Weight: 243 lbs
Real Name: Richard Fliehr
Hometown: Charlotte, North Carolina
Other Names: Rick Flair, "The Nature Boy" Ric Flair(NWA/WCW, WWF/WWE, TNA), "Slick Ric"
Wrestler Since: 1972
Finishing Maneuver: Figure-Four Leglock
Previous PWI 500 Rankings: #19(2008), #70(2007), #24(2006), #51(2005), #30(2004), #53(2003), #34(2002), #43(2000), #42(1999), #55(1998), #35(1997), #10(1996), #20(1995), #3(1994), #6(1993), #3(1992), #3(1991)
Other Related Websites:
History: (Last Edited: 5/01/06)
The Four Horsemen - Rollercoaster Bio
Fortune - Rollercoaster Bio
Immortal - Rollercoaster Bio
Ric Flair - Cagematch Bio
Ric Flair - Online World of Wrestling Bio
Ric Flair - Wikipedia Bio
Ric Flair.Com (Unofficial Fan Site)
Weight: 243 lbs
Real Name: Richard Fliehr
Hometown: Charlotte, North Carolina
Other Names: Rick Flair, "The Nature Boy" Ric Flair(NWA/WCW, WWF/WWE, TNA), "Slick Ric"
Wrestler Since: 1972
Finishing Maneuver: Figure-Four Leglock
Previous PWI 500 Rankings: #19(2008), #70(2007), #24(2006), #51(2005), #30(2004), #53(2003), #34(2002), #43(2000), #42(1999), #55(1998), #35(1997), #10(1996), #20(1995), #3(1994), #6(1993), #3(1992), #3(1991)
Other Related Websites:
History: (Last Edited: 5/01/06)
Richard Morgan Fliehr began his life under a different name, in a different life. He was born in February '49, and was immediately taken away from his real parents and sent to the Tenneessee Children's Home Society, which later became infamous for its stealing away of over 5,000 children by tricking the parents into signing adoption papers. Only a few weeks later, the child was legally adopted by Dick & Kay Fliehr, and had his name legally changed. This was the true beginning of Fliehr's life, as his adopted parents shaped the path of his future.
As a two-time Wisconsin Private School Wrestling Champion in '66 and '67, Ric Fliehr quickly showed what his future held in store for him. However, Fliehr, while a great athlete, had trouble keeping up with the intellectual portion of school, preferring instead to enjoy the finer things in life. This led to Fliehr dropping out of the University of Minnesota his sophomore year. Fliehr worked various jobs after dropping out, from selling insurance door-to-door to being a bouncer for a club in Minneapolis. It was through the club that Fliehr made friends with Olympic hopeful Ken Patera, and through him, began training with legendary wrestler and promoter Verne Gagne.
On December 10th, 1972, Ric Flair made his wrestling debut, fighting to a Draw with George "Scrap Iron" Gadaski. Flair would face many great stars while wrestling for the American Wrestling Association, including Dusty Rhodes, Andre the Giant, Larry "The Ax" Hennig, and Wahoo McDaniel, just to name a few. After only a few years with the company, though, Flair, through contacts with McDaniel, opted to move on, leaving for the NWA Mid-Atlantic Championship Wrestling organization in 1974.
NWA Mid-Atlantic: 1974-1975
Flair immediately began to make an impact as soon as he came to Charlotte, teaming up with Rip Hawk to form a dangerous tag-team. The duo won the NWA Mid-Atlantic Tag-Team Titles in July '74, beating Bob Bruggers & Paul Jones. They would hold the belts for nearly a year, before dropping them in February '75 to Jones & his new partner, Tiger Conway Jr. Around the same time, though, Flair compensated by winning his first singles gold, taking the Mid-Atlantic Television Title from Jones, continuing their feud. Jones would win back the title later in the year, only to have Flair regain it in June '75. Flair's 2nd reign only lasted a week, though, before Jones took back the belt.
Once again, though, Flair found a way to turn a negative into a positive. In July '75, Flair made his way to the top of the organization, winning the Mid-Atlantic Heavyweight Championship. It was a short but memorable reign, as Wahoo McDaniel beat him for the belt by the end of July. Flair was persistant, though, having a long-running feud with McDaniel over the next few months. In September '75, Flair managed to regain the Mid-Atlantic Heavyweight Title, taking down McDaniel. Their feud, though, was set to continue for some time.
The Plane Wreck
Just as it seemed that Flair's career was about to explode, an event occurred that nearly ended it, as well as Flair's life. On October 4th, 1975, Flair joined Johnny Valentine, Bob Bruggers, Tim Woods, and David Crockett in a Cessna 310, piloted by Mike Farkas. In one of those ironies that goes with disasters, both Bruggers and Crockett were substitutions, as Wahoo McDaniel opted to drive and David's brother, Jimmy, was too sick to fly. When the plane had more than half-way covered its destination, it ran out of fuel, due to a miscalculation by the pilot. The plane crashed at a bad angle, sending wrestlers tumbling everywhere. Farkas died in the crash after a long time in a coma. Bruggers and Valentine never wrestled again. Flair broke his back in three places, and many speculated that he would never wrestle again.
Despite what others had to say, though, Flair had no intention of giving up his professional career. After months of recuperation, Flair made his return in early '76, still holding onto the NWA Mid-Atlantic Heavyweight Title that he had been holding before the accident. The feud with McDaniel began right where it had left off, with Flair still the heel that everyone wanted to see fall. In May '76, it happened, as Flair dropped the belt to McDaniel. Only a few weeks later, though, Flair managed to reclaim the gold for the third time, cheating to win, as always. He kept the Heavyweight Title for another four months, with McDaniel taking the belt away again. Flair answered back in October '76, becoming a four-time Mid-Atlantic Heavyweight Champ. This reign lasted another month and a half, as McDaniel snatched back the belt before the end of the year. The two men continued to have an incredible feud for some time, while being good friends behind the scenes.
After losing the Heavyweight Title, Flair began teaming up with Greg "The Hammer" Valentine, the son of the man he was on the plane with, Johnny Valentine. The duo quickly managed to win the NWA World Tag Team Titles from the Minnesota Wrecking Crew (Gene & Ole Anderson) in December '76. The two reigned as champs until May '77, when the Crew won the belts back. For a time, Flair was wearing two belts at once, as he had won the Mid-Atlantic Television Title for the 3rd time in April '77 from Rufus Jones. Flair successfully defended the title for the next few months, but was shockingly upset by a debuting Ricky Steamboat in June '77, creating a feud that lasted for many years.
For a few weeks, Flair had to live without gold around his waist. Of course, he wouldn't let this last. In early July '77, Flair & Greg Valentine managed to arrange for them to be awarded the Mid-Atlantic Tag-Team Titles, Flair's second run with the belts. A short time later, Flair also earned a new belt, the NWA United States Heavyweight Title, taking down Bobo Brazil. This gave Flair and Steamboat two titles to feud over, with Flair staying with Valentine as Steamboat began teaming with Paul Jones. In August '77, Flair & Valentine lost the Mid-Atlantic Tag Titles to Steamboat & Jones. Flair and Steamboat continued to meet in furious battles wherever they went, usually selling out the stadiums. In October '77, Steamboat finally managed to beat Flair for the US Title, ending another reign for the Nature Boy, as he was becoming known (in homage to a former NWA star, "Nature Boy" Buddy Rogers).
Once again, Flair quickly compensated for the lack of gold around his waist, as he & Valentine were able to beat the Minnesota Wrecking Crew the next week for the 2nd time, regaining the NWA World Tag-Team Titles. Flair & Valentine continued to make a solid tag-team in the Mid-Atlantic federation, as well as other organizations, representing the National Wrestling Alliance for the rest of 1977 as their tag-team champions.
In April '78, Flair & Valentine were stripped of the NWA World Tag-Team Titles, leaving Flair to head back into the singles ranks. This wasn't a problem for Flair, as he soon defeated Mr. Wrestling (Tim Woods) to become the 2-time NWA United States Heavyweight Champion. This led to more encounters with Ricky "The Dragon" Steamboat, as the two men feuded for much of the rest of the year. Flair also found himself a new partner in Big John Studd, with the two winning the Mid-Atlantic Tag-Team Titles together at the end of October '78 from Steamboat & Jones. The victory was short-lived, as Steamboat & Jones regained the titles the next week. Near the end of the year, Flair lost the US Title again to Steamboat, and for the first time in years, ended a year without wearing a major title.
After months of attempts and failures, Flair finally managed to beat Steamboat in April '79 to get the NWA United States Title back around his waist. Flair continued to match up against Steamboat routinely over the next few months, as well as having other feuds, including several notable encounters with his namesake, "the Nature Boy" Buddy Rogers. At "The Battle of the Nature Boys" in July, Flair was able to beat the legendary star via the Figure Four Leglock, staying the true Nature Boy in the sport. Flair continued to defend the US Title for another month, until he was forced to vacate the belt after he and Blackjack Mulligan won the NWA World Tag-Team Titles from Paul Jones & Varon von Raschke. Unfortunately for Flair, he & Mulligan lost the belts back to Jones & Raschke only a few weeks later, leaving Flair without either a singles or a tag belt to call his own for a time.
After a few months without gold, Flair became a four-time NWA US Heavyweight Champion in April '80, taking down "Superfly" Jimmy Snuka. Flair ran with the belt for the next few months, enjoying his status as the champ. But Flair had a new challenger to his gold, his old friend and tag-team partner, Greg "The Hammer" Valentine, who beat Flair for the gold in July '80. Flair and Valentine continued their feud for the next five months, with Flair regaining the NWA United States Heavyweight Title in November '80, becoming a 5-time US Champ. It was another milestone for Flair, as he continued to gain respect and honor across America, as well as the rest of the wrestling world.
Going into the new year, Flair, now as a fan favorite, began feuding with another up-and-coming star in "Rowdy" Roddy Piper. Near the end of January '81, Piper, as the Mid-Atlantic Television Champion, defeated Flair to take away the United States Title. The cocky Piper later tried to give Flair the Television Title, saying that he didn't need it anymore. Flair refused, though, saying that he didn't wear anything that he didn't win. The TV belt was vacated, as Flair and Piper continued to feud over the United States Title. Despite his great skills in the ring, though, Flair was unable to take the belt back from Piper. It didn't seem to matter, though, as Flair was beginning to set his sights towards something much higher.
One of the most respected titles in all of wrestling at the time was the NWA World Heavyweight Title. It was the strap that connected several large wrestling organizations, with the champion being called on to wrestle in every one. In September '81, Flair realized the dream of many wrestling super-stars, as he managed to win the NWA World Heavyweight title from Dusty Rhodes. It was Flair's first singles World Title reign, a major accomplishment for a wrestler. Flair would defend the belt all over the world, from facing down Jumbo Tsuruta in Japan for AJPW, to wrestling to a double count-out against the WWWF World Heavyweight Champion, Bob Backlund, to defending against stars like Rhodes, Kerry von Erich, and others.
One of the more interesting incidents occurred in the Dominician Republic, when Flair headed there to face off against Jack Veneno. At the time, wrestling was still considered an actual sport, as the wrestlers worked hard to keep the kayfabe alive. The fans in the country were ravenous, as they heavily rooted for Veneno. The match ended in a 60-minute draw, just as Flair seemed about to submit to Veneno's sleeper hold. The place rioted, with everyone believing that Veneno had actually won, and rather than add to the violence, Flair left without the World Title, leaving it with Veneno. Flair returned later on, to try to 'regain' the gold. But due to the violence of the situation, Flair allowed Veneno to pin him, then later was given back the title, without the NWA acknowledging the transfer of the belt.
Flair's main rival back in the States continued to be Dusty Rhodes, whom almost won the NWA Title from Flair in February '83 under a mask as the Midnight Rider (since Rhodes, at the time, wasn't supposed to compete, having lost a "Loser Leaves Town" Match). When NWA President Bob Geigel told Rhodes he would have to unmask to be the champ, Rhodes was forced to give the belt back to Flair, saving the title. Flair next concentrated on a feud with Harley Race, who finally stopped Flair's title reign in June '83. After Flair executed a suplex to try and hold Race down to the mat, Race got his shoulder up, while Flair didn't. Flair compensated the next month for the lost title, defeating Bob Brown, George Welles, Butch Reed, and finally David von Erich in a tournament to win the vacated NWA Missouri Heavyweight Title. He would stay the champion for the next two months.
Flair's thoughts, however, never left the NWA World Title, as it was arranged for Flair to take on Harley Race at the first Starrcade: Flair For The Gold. Flair was the huge fan favorite coming into the match, having had to deal with Race putting a $25,000 bounty on Flair's head. Flair's friend at the time, "Cowboy" Bob Orton, turned on Flair during a match, with Orton, Race, and Dick Slater beating down the challenger. Flair, with a supposedly injured neck after the assault, announced his retirement, but soon came back to take out both Slater and Orton. At Starrcade, with Gene Kiniski as the special referee, Flair won a bloody "Steel Cage" Match over Race to regain the NWA World Heavyweight Title, becoming a 2-time champion.
In March '84, while on an international tour, Flair dropped the World Title to Race. Only a few days later, in another country, Flair regained the gold, setting himself up for another run with the belt. A few months later, Flair faced off against Kerry von Erich at the David von Erich Memorial Parade of Champions. The emotions were running high, especially after Kerry defeated Flair for the NWA World belt. Just a few weeks later, though, Flair climbed back to the top, dethroning von Erich to get the belt for the 4th time. Flair then spent the rest of '84 as the NWA World Champion, being the major face of the organization to counter the rising threat of the WWF. In October '85, Flair wrestled to a draw with the AWA World Champion, Rick Martel. Flair also had a great showing at Starrcade '84, where he was victorious over Dusty Rhodes, due to special referee "Smokin'" Joe Frazier stopping the match due to Rhodes' blood loss.
Two major developments in '85 began to take Flair's wrestling career on a new course. First, Crockett Promotions, Flair's main organization, merged with Georgia Championship Wrestling to create World Championship Wrestling, or WCW. Second, Flair began teaming up with his 'cousins', Arn & Ole Anderson, and Tully Blanchard, with J.J. Dillon as their manager, forming one of the greatest stables of all time, the Four Horsemen. The group helped Flair stay on the top of the NWA, with Flair gaining a victory at the Great American Bash '85 over Nikita Koloff and retaining the belt, but losing, via DQ, to Dusty Rhodes at Starrcade '85. The symbol of raising four fingers in the air became an infamous sign in professional wrestling, thanks to this group.
Flair continued to defend the NWA World Title against all comers in '86, although many of his matches were regulated by WCW. Flair had various feuds with Barry Windham, Ricky Morton (of the Rock 'n' Roll Express), among others. During the Great American Bash '86 series, Flair won a "Steel Cage" Match over Morton. A few weeks later, though, Flair lost a bloody "Steel Cage" Match to Dusty Rhodes, dropping the title. Just a few weeks later, after the Four Horsemen had badly injured Rhodes' leg, Flair forced Rhodes to pass out to the Figure Four, getting the NWA World Title for the fifth time. Flair would spend the rest of the year as the champion, including getting a DQ win over Nikita Koloff at Starrcade '86.
The Four Horsemen ruled the NWA/WCW area in '87, with, at various points, Flair as the World Champion, Blanchard as the Television Champion, and Arn Anderson & Blanchard as the World Tag Champs. Early in the year, though, a replacement was made, as Ole Anderson was taken out of the group and replaced by Lex Luger. At the Great American Bash '87, Flair, Anderson, Blanchard, Luger, & JJ Dillon faced off against Rhodes, Koloff, the Road Warriors, & Paul Ellering, with Flair's team unfortunately coming up on the losing side of the equation. Luger later turned into a fan favorite, refusing to let J.J. Dillon win the Bunkyard Stampede Battle Royal in December. Luger left the Horsemen, leading to a long protracted feud, which included Barry Windham, Luger's tag-team partner, turning on him and taking his place in the IV Horsemen.
In September '87, Flair lost the NWA World Title to Rugged Ronnie Garvin in a "Steel Cage" Match (which kept the IV Horsemen from interfering). Flair immediately began to try to plan to get the belt back, and faced off against Garvin at Starrcade '87. After another brutual "Steel Cage" Match, Flair got the victory by sending Garvin into the steel and getting the quick pin. Flair thus gained the NWA World Title for the sixth time, although the NWA/WCW contingent only recognized 5 of the reigns (leaving out Flair's trade of the title with Harley Race away from the States).
One of Flair's greatest feuds started in '88. At Clash of the Champions I, Flair went up against a young newcomer calling himself Sting. It was the first meeting between the two wrestlers, and Flair came off overconfident early on. But Sting quickly proved his worth, and the two wrestlers went for a 45-minute draw, with Flair trapped in the Stinger Deathlock at the end. This immediately made Sting a star, creating a new rival for Flair to feed off of. Flair also had his old foes, as well, and defeated Lex Luger via blood loss (Luger couldn't continue) at the Great American Bash '88. For the rest of the year, Flair & the IV Horsemen feuded with Luger, with Flair getting another tainted win over him at Starrcade '88.
At the beginning of '89, Flair & Barry Windham agreed to a match with Eddie Gilbert and a "mystery" partner. The partner turned out to be Ricky Steamboat, who had come out of retirement. Due to Flair & Windham losing to Steamboat & Gilbert that night, Flair fired J.J. Dillon for not adequately preparing them, and hired Hiro Matsuda instead. It was during this period that the "Horsemen" name was put on the shelf, since most of the members had departed for the WWF (Arn & Tully became the Brain Busters, and Windham became the "Widowmaker").
Flair and Steamboat had a series of great matches, leading up to the Chi-Town Rumble in February '89. Flair lost the NWA Title to Steamboat when Steamboat caught him with an inside cradle, pinning him to the mat. Flair immediately began pursuing the gold again, challenging Steamboat at every opportunity for the belt. He became obsessed, telling Hiro Matsuda to let him go after the title alone, breaking off from the Yamazaki Corporation. At Clash of the Champions VI, Flair and Steamboat had a "Three Falls" Match for the NWA World Title. Flair pinned Steamboat in the first fall, but was forced to submit to a standing double-chicken-wing for the second. Steamboat then pinned Flair to retain the title.
Flair didn't give up trying, however, and faced off against Steamboat again at WrestleWar '89 (also called Music City Showdown). With three ringside judges (Lou Thesz, Terry Funk, & Pat O'Connor) looking on, Flair pinned Steamboat to become the 7-time NWA Heavyweight Champion. After the match, Flair and Steamboat showed their respect to each other, getting the cheers of the crowd. Flair then began an interview, talking about the win. It was interrupted, though, by one of the judges, Terry Funk, who said he wanted to challenge for the title. When Flair told him it wouldn't happen, since Funk wasn't on the contenders' list, Funk snapped, attacking Flair and taking him outside, piledriving him through a table! Flair was out of action for more than a month afterwards, mulling over retirement due to a neck injury.
But Flair came back from the piledriver to get his revenge on Funk. The two men met at the Great American Bash '89, with Flair getting the victory. This didn't stop the feud, though, as Flair and Funk met up several times over the next few months, with Flair, now as a fan favorite again, joining up with Sting on occassion, as well as a semi-retired Ole Anderson. At Halloween Havoc '89, Flair & Sting faced off against Funk & the Great Muta (Sting's rival) in a "Thunderdome" Match, with Bruno Sammartino as the guest referee. Once again, Flair's team got the win, but things still weren't settled.
This led to Flair and Funk finally deciding to settle things with an "I Quit" Match at Clash of the Champions IX. An added stipulation was that the loser would have to shake the hand of the winner and tell him that he's the better man. The two men had a brutal brawl, showing the hatred that each had for the other. In the end, Flair latched on the Figure Four Leglock, holding it unmercifully until Funk finally said that he quit. After the match, Funk followed through with the stipulation, shaking Flair's hand.
In December '89, Flair was continuing a feud with the Great Muta, and was in danger of being double-teamed. Surprisingly, Arn & Ole Anderson ran down to the ring to make the save. The three men, along with Sting, reformed the IV Horsemen (Tully Blanchard was going to return as well, but tested positive for cocaine and was not given a contract). It seemed like a great match, but things soon started falling apart between Flair and Sting. At Starrcade '89, in the Iron Man tournament, Flair met Sting in the finals (having beating the Great Muta and fought to a Draw with Luger). Sting upset the champion, winning the tournament and getting a World Title shot.
As the IV Horsemen moved into the new year, there was definite tension, as Flair seemed worried about Sting's desire to challenge him for the NWA World Title. In February '90, Flair & the rest of the Horsemen told Sting to give up the title shot at Clash of the Champions X, but Sting refused, leading to the Horsemen beating him down. Later in the night, during the Horsemen's "Steel Cage" Match with Buzz Sawyer, the Great Muta, & the Dragon Master, Sting ran down to attack, only to injure his leg on the cage, putting him out of action for a time, much to Flair's relief.
In March '90, the IV Horsemen regrouped, with Barry Windham returning from the WWF to rejoin the group. Sid Vicious also became a member, as Ole Anderson stepped aside to become the manager of the faction. With Sting out for a time, Flair feuded with Lex Luger, each match usually having a 'unique' ending. At WrestleWar '90, Flair won via countout, and at Capital Combat, a DQ loss saved Flair's title (with the Horsemen attempting to save Flair). Finally, Sting made his return, and was given the title shot that he had earned at the Great American Bash '90. When Flair went for the Figure Four, Sting rolled him up and got the 3 count, winning away the World Title.
Flair and the rest of the Horsemen pursued Sting's World Title in the coming months, including sending Vicious to challenge Sting at Halloween Havoc '90. In the match, a strangely-off Sting seemed to be having no luck against Vicious, and was pinned, apparently losing the title. As "Sting" headed towards the back, he had a big grin on his face, and a loose flap of 'skin' coming off his head. The real Sting then came out, having escaped from where the Horsemen were holding him in the back, and attacked, revealing the imposter as Windham. Sting eventually went on to beat Vicious and retain the title. Flair wasn't done, though, and underwent a 'transformation' of a sort, playing mind games with Sting as the masked Black Scorpion. Sting was eventually able to beat the Black Scorpion, though, at Starrcade '90,, despite the presence of several masked men at ringside. Sting managed to unmask the head Scorpion, revealing Flair's attempted trickery.
Flair and Sting's battles didn't stop with the unmasking. In January '91, Flair finally managed to regain the World Title, beating his long-time nemesis. It was announced that the title would now be known as the WCW World Heavyweight Title. Flair, as the champion, feuded with El Gigante, a 7'6" giant, as well as Sting and the Steiner Brothers. In March '91, WCW headed to Japan for a show with New Japan Pro Wrestling, entitled Starrcade in Egg Dome. It was here that Flair defended the NWA/WCW Title against Tatsumi Fujinami. In a strange finish, Fujinami pinned Flair, but only after Fujinami had thrown Flair over the top rope earlier on, an illegal maneuver in WCW. It was ruled that Fujinami had won the NWA Title, but Flair was still the WCW Heavyweight Champion, splitting apart the belts. A few months later, at SuperBrawl I, Flair beat Fujinami by grabbing the tights, re-unifying the two titles.
Flair next feuded with Bobby Eaton, beating him in a "Three Falls" Match at Clash of the Champions XV. But by this time, Flair's chief feud was with the financial office, and with the man in charge of WCW at the time, Jim Herd. While Flair was still the WCW Champion, a contract agreement could not be reached, as the people in charge were looking for a cut in salary, something that Flair didn't agree with. Since there was no contract renewal, it was first thought that Flair would lose the title to Lex Luger at the Great American Bash '91. This then changed to having Flair lose to Barry Windham a few days before, and have Windham defend against Luger. Finally, though, it was decided to simply give Flair his release, which turned out to be a terrible decision for WCW, as Flair took his World Title with him when he headed to the competition.
In August '91, Bobby "The Brain" Heenan, a long-time manager, began touting that the "Real World's Champion" was coming to the World Wrestling Federation. Soon, Flair made his first appearance, wearing the NWA/WCW World Title as his own. Flair & Heenan were soon joined by Mr. Perfect, who became part of Flair's staff. Flair's first pay-per-view for the WWF was The Survivor Series '91, where Flair teamed up with "The Million Dollar Man" Ted DiBiase, the Warlord, & the Mountie against "Rowdy" Roddy Piper, "The British Bulldog" Davey Boy Smith, Bret "Hitman" Hart, and Virgil. Flair had the first effect, eliminating Smith. Piper's team struck back, though, by taking out their biggest weapon, the Warlord. Soon afterwards, both teams broke down, brawling outside the ring. Only Flair was smart enough to get back in the ring in time, avoiding the countout and winning the match.
Going into the new year, the main topic around the WWF was the vacated WWF World Heavyweight Title. Problems between Hulk Hogan and the Undertaker had led to the belt being held up by President Jack Tunney, and the ruling was that the winner of the 1992 Royal Rumble would become the new champion. Flair decided that this was his chance to bring both his belts together, and was considered one of the favorites going in. His hopes appeared to be dashed, however, when Flair entered at #3, a terrible draw. Bobby Heenan, who was one of the announcers for the event, added his own angst and struggling to the match, making Flair the center of attention. Time and time again, Flair seemed about to go out, yet would somehow hang on. Inbetween these times, Flair eliminated the British Bulldog, Kerry von Erich, and the Big Boss Man. In the end, Flair was in the Final Four. Sid Justice (known as Sid Vicious in WCW) got rid of "Macho Man" Randy Savage, then shockingly tossed Hulk Hogan while Hogan was busy with Flair. Hogan, upset, grabbed Justice's arm from the outside, overbalancing him enough so that the exhausted Flair could toss him out, winning the Rumble and becoming the undisputed WWF World Champion.
Flair would feud with the top faces in the company for the next few months, eventually focusing on Randy Savage. Flair used his mind games along with Heenan & Perfect, announcing that Flair had been seeing Miss Elizabeth, Savage's valet (& wife), in intimate situations. Flair even produced doctored photographs that seemed to show he and Elizabeth hanging out together, although Savage & Elizabeth were able to show the original photos, which featured Savage, not Flair. At Wrestlemania VIII, Flair and Savage met up for the WWF Heavyweight Title. Mr. Perfect, from ringside, interfered constantly, giving Flair a foreign object to use at one point. Despite everything, though, Savage was able to roll Flair up for the victory, taking away the title. After the match, a bloody Flair forcibly kissed Elizabeth, elicting a slap from Elizabeth, followed by another brawl with Savage.
Flair continued to feud with Savage over the summer of '92, with Flair bringing in Razor Ramon (Scott Hall) as another ally. In September '92, at a television taping, Flair, with help from Mr. Perfect & Ramon, made Savage pass out from the Figure Four, becoming a 2-time WWF World Champion. Flair seemed set for a nice reign as the champion, with many opponents to go against. However, a fluke injury occurred in October, when, after an Ultimate Warrior suplex was botched, Flair had a bone chip in his inner ear break loose and cause dizziness, upsetting his equilibrium. Flair, unable to perform, quickly dropped the World Title to Bret Hart, then eventually recovered from the problem. It was around this time that Flair had a major falling out with Mr. Perfect, with the two beginning to feud. At the '92 Survivor Series, Flair & Razor Ramon tagged against "the Perfect Team", Mr. Perfect & Savage. Flair & Ramon lost via DQ.
Going into the new year, Flair once again set his sights on winning The '93 Royal Rumble. It seemed likely that Flair, who had proved he could last a long time, would get a better draw. Yet somehow Flair beat the odds, entering this time as the #1 entrant and facing off against Bob Backlund at the beginning. Flair managed to toss out Papa Shango (later known as the Godfather), but couldn't last as long as last year. He was eventually tossed out by his rival, Mr. Perfect. Not long after the pay-per-view, Flair and Mr. Perfect agreed to have a "Loser Leaves Town" Match on Raw. Despite Flair's best efforts, Mr. Perfect got the victory with the Perfect Plex, ending Flair's short-but-successful stint with the World Wrestling Federation.
Flair made his triumphant return to World Championship Wrestling in February '93, immediately rejoining with his good friend, Arn Anderson. For a while, Flair ran a "talk show" of sorts on WCW television (since he had to wait out his no-compete clause from the WWF). During one of these shows, Flair brought out "Pretty" Paul Roma, who would join with Flair, Arn, & Ole Anderson as the newest reincarnation of the IV Horsemen. The group worked as fan favorites, feuding with the Hollywood Blondes (Brian Pillman & Steve Austin), among others. In June '93, at Clash of the Champions XXIII, Flair & Arn Anderson took on the Hollywood Blondes in a "Three Falls" Match for the Blondes' WCW Tag-Team Titles. Flair & Arn won the match, but since one of the falls was a disqualification victory, the Hollywood Blondes kept the belts.
Flair did find other gold to go after, however. In July '93, Flair defeated former Horsemen Barry Windham at Beach Blash '93 to regain an old friend, the NWA Heavyweight Title (which was a separate title from the WCW World Heavyweight Title). This was Flair's 10th reign as NWA Champion, although it was possibly the least prestigious, as the title no longer held as much meaning as it once had. At Fall Brawl '93, Flair lost the NWA Title (now called the WCW International Heavyweight Title) to "Ravishing" Rick Rude. Flair tried to regain the belt from Rude at Halloween Havoc '93, but lost via DQ.
So Flair aimed towards the WCW World Heavyweight Title, which was currently being held by the monster named Vader. At successive PPVs, Flair met up against the monster, and couldn't manage to snatch away the title. Finally, at the biggest stage of the year, Starrcade '93, Flair and Vader met up with the belt on the line. Flair had spoken before the match that, if he couldn't win the title this time, he would retire. The two men had a brutal match, pulling no punches against the other. Vader had his manager, Flair's old foe Harley Race, aiding him, but Flair had the fans behind him, and managed to roll up Vader for the pin, becoming a 2-time WCW World Heavyweight Champion (14-time World Champion over-all).
Flair continued as a face for the next few months, as he continued to meet up with Vader at several pay-per-views, always managing to come out with the title. At Superbrawl '94, Flair and Vader settled things in a "Thundercage" Match, with the Boss (the Big Boss Man) as the special guest referee. Flair again came out victorious, staying the champion. Flair then entered into a feud with his long-time adversary, Ricky "The Dragon" Steamboat. By now, Flair was beginning to become a heel again, with Arn Anderson by his side. In April '94, Flair and Steamboat wrestled a competitive match, that ended with both men's shoulders on the mat for the 3 count. This led to the WCW World Title being held up. A week later, the two wrestlers met again, and this time Flair won out, reclaiming his World Title. Flair would add another prize soon enough, as he defeated Sting at Clash of the Champions XXVII to unify the WCW World Title with the WCW International World Title, ending the run of that belt.
In the summer months, Flair had to deal with "the Immortal" Hulk Hogan, who had come over from the WWF (in part due to Flair's backstage negotiations). At Bash At The Beach '94, Flair and Hogan went at it for the WCW World Title. Flair had "Sensational" Sherri in his corner, while Hogan brought a posse of Jimmy Hart, Shaquille O'Neal, and Mr. T. Sensational Sherri did her best to interfere, taking out the referee at one point, and giving Flair brass knuckles to hit Hogan with at another. Yet Flair couldn't keep the Hulkster down, and finally, after Hulking Up, Hogan got the Big Legdrop and won the match, taking away the World Championship.
At Clash of the Champion XXVIII, Flair got a rematch against Hogan. He also got some help from a masked man, who tried to take out Hogan's knee (I believe this was later revealed to be the Butcher, aka Ed Leslie, but I'm not certain). Hogan was eventually counted out due to the pain in his leg, giving Flair the win, but not the title. The final match of the competition was set up for Halloween Havoc '94, with Flair putting his career on the line. The bout was a "Steel Cage" Match, with Hogan having the odds stacked in his favor by having Mr. T as the special referee. Flair fought hard, knowing the stakes, but he couldn't complete it, as Hogan won out, apparently ending Flair's career in WCW.
At WCW Uncensored '95, "Macho Man" Randy Savage was wrestling against Avalanche (John Tenta). During the match, a woman could be seen at ringside. A strangely proportioned woman. The 'woman', aka Flair in drag, attacked Savage, causing the DQ. Flair was quickly revealed, as he brought Savage into the ring to help Avalanche squash him. Later on, Flair & Arn Anderson tried to help out Vader in his "Strap" Match against Hogan for the World Title. In a strange twist, though, Hogan managed to get the strap on Flair, then dragged him to all four corners, which apparently counted as the win. For a while afterwards, Flair tried to get reinstated to active status as a wrestler, with Hogan & Savage (for less pleasing reasons) asking for the same thing. The WCW Board of Directors relented, bringing Flair back to the ring.
Flair teamed up with his former enemy, Vader, to take on Hogan & Savage at Slamboree '95. Savage had his father, former wrestler Angelo Poffo, at ringside, as the bout took place. Hogan & Savage won out, but Flair got some revenge, taking out Poffo before he left. Flair and Savage fought again at The Great American Bash '95. Poffo was once again at ringside, but this proved to be more of a detriment for Savage, as Flair was able to steal Poffo's cane and hit Savage, knocking him out and allowing Flair to get the pinfall. Savage got revenge the next month, though, winning a "Lifeguard Lumberjack" Match over Flair at Bash At The Beach '95.
Flair & Anderson next had to deal with a falling out with Vader. The three men signed to have a "Handicap" Match at Clash of the Champions XXXV. Although Flair & Arn had the advantage, problems between them allowed Vader to capitalize and win out. After the match, Flair and Anderson continued to have issues, which eventually led to the two long-time friends opting to sign a match to face off at Fall Brawl '95. It was an epic match, that had many WCW wrestlers come out to watch, since the two men had never faced off before. After a lot of back-and-forth action, the ending was marred when "Flyin'" Brian Pillman opted to interfere, nailing Ric with a huge kick from the outside to allow Anderson to get the pin and the victory.
Flair continued to feud with Anderson & Pillman for a time, with his foes claiming to be the "real" Horsemen. Flair started asking Sting to be his tag-team partner, but Sting didn't trust the Nature Boy. Flair helped prove his point somewhat, though, taking on Anderson & Pillman in a "Handicap" Match, which Sting eventually coming out to help. After much pleading by Flair, he got Sting to join up with him as his partner against Anderson & Pillman at Halloween Havoc '95. Before the match, though, Flair was apparently taken out, leaving Sting this time to fight in a "Handicap" Match. After holding his own for a while, Sting was finally joined by Flair, who desperately wanted to make the tag. But when it happened, Flair turned on Sting, joining with Anderson & Pillman to beat the man down.
Flair and Sting had it out a month later at World War III '95, in a brutal match that saw Sting take the victory. Later on, Flair competed in the Battle Royal as well, but again couldn't last, especially with how spent he was. Flair did get a boost, though, with the addition of Chris Benoit to make the IV Horsemen again a complete set. At Starrcade '95, Flair was entered into a "#1 Contenders Triangle" Match against Lex Luger and Sting. Flair, with the Horsemen nearby, got the victory, to earn a World Title shot against Savage that night. Thanks to a lot of interference from all three Horsemen, especially with Anderson using some brass knuckles on Savage, Flair got the victory, again becoming the WCW World Heavyweight Champion.
Only a few weeks into '96, Flair dropped the title back to Savage, after a miscue from Anderson ko'ed the wrong wrestler. Things weren't settled between the two, though, so a "Steel Cage" Match was signed between Flair and Savage at Superbrawl '96. Flair had his former manager, Woman, in his corner, while Savage had Miss Elizabeth. During the match, Woman tried to interfere on Flair's behalf, with limited results. Miss Elizabeth, though, proved to be the deciding factor, as she turned on Savage and handed Flair a shoe to knock him out with, allowing Flair to regain the WCW World Heavyweight Title, his 5th official reign (and 17th World Title reign over-all).
After a few months at the top, Flair had to face the challenge of the largest athlete in the world, the Giant. Despite the help of the IV Horsemen (which was actually only Anderson & Benoit, since Pillman was no longer with the company), Flair couldn't stop the Giant, losing the World Title to him. Still, Flair continued to work with Anderson & Benoit as a strong group, looking for one more recruit. At the Great American Bash '96, Flair & Anderson signed to fight two former football stars in Kevin Greene and Steve "Mongo" McMichael. In a startling twist, though, McMichael turned his back on Greene and instead joined the IV Horsemen, getting the group up to the numbers. A month later, at Bash At The Beach '96, Flair gained the United States Heavyweight Title for the 6th time, beating Konnan. Flair would hold the belt for the next few months, while joining in feuds against the growing threat of the new World order, but tore his rotator cuff during a match in September '96 with Kensuke Sasaki in the Japan/United States All-Star Tournament, leaving him badly injured. He eventually vacated the title.
After his return from the shoulder injury, Flair teamed some with "Rowdy" Roddy Piper against the nWo, challenging the Outsiders for the Tag-Team Titles at the Great American Bash '97. The Outsiders won out, though, and Flair & Piper had a falling out, eventually facing off against each other at Bash At The Beach '97, where Piper won out by putting Flair to sleep. Flair & the rest of the Horsemen became a major power front for WCW, even as the nWo tried to take over the organization. Unfortunately, one member of the Horsemen was not going to be able to help out. Arn Anderson, who had had Jeff Jarrett 'unofficially' replace him in the Horsemen for a time, announced his retirement at the end of August '97, with Curt Hennig (formerly Mr. Perfect in the WWF) picked to take over his spot. This seemed like a good choice, but it couldn't have backfired worse, as Hennig turned on the Horsemen at Fall Brawl '97, joining with the nWo force to help destroy the Horsemen in the War Games match.
Flair sought his revenge against Hennig over the next few months, first facing him at Halloween Havoc '97, with the United States Title around Hennig's waist on the line. Just when Flair seemed to have Hennig's number, though, the nWo interfered, causing the DQ. The two hated foes met again at World War III '97, again with the gold on the line. Near the end, Flair had Hennig in the Figure Four Leglock, and seemed to be about to get the victory, when Hennig got hold of his US Title and clocked Flair with it, knocking him out. Hennig then got the pin for the victory, keeping Flair from his revenge. Flair then faded into the background for a few months, recovering from the decimation of the Horsemen.
Flair started out '98 feuding with Bret "Hitman" Hart, who had come to WCW after the Montreal Screwjob in the WWF. Flair and Hart had arguments about who the best technical wrestler was, and ended up facing off at Souled Out '98. Although Flair put on a strong showing, the younger Hart won out, making Flair submit to the Sharpshooter. Flair's contract with WCW expired in February '98, but Flair continued to work with the company, while working on another deal. However, in April '98, Flair's son, Reid, qualified for the AAU National Wrestling Tournament (he went on to win). Flair, a proud father, asked for time off to see the tournament. Instead, the current manager, Eric Bischoff, refused. Flair took the time off, anyway, and was promptly 'fired' by Bischoff and sued for Breach of Contract (even though Flair wasn't currently UNDER contract!). Flair answered back with a counter-suit, leading to a 4-month legal battle.
In September '98, Flair came out on a Monday Nitro to a huge explosion by the audience. He joined Arn Anderson, Chris Benoit, Steve "Mongo" McMichaels and Dean Malenko (who had been pushing hard for Anderson to bring the group back) in the ring, and effectively restored the Four Horsemen. Flair then proceeded to lead the Horsemen into a war against Eric Bischoff and the nWo Black 'n' White. Flair and Bischoff had many altercations, including his son, Reid, out-wrestling Bischoff, and a controversial staged heart attack by Ric. The "heart attack" was later changed to Flair having been poisoned, apparently by Bischoff. Flair and Bischoff met at Starrcade '98, where, due to nWo interference (specifically Curt Hennig), Flair lost. However, the two met again a few days later during a Monday Nitro. Flair, with the Horsemen keeping the nWo occupied, defeated Bischoff to become the WCW President for 90 days (if Flair had lost, he would have retired).
With Flair as the President, things started heating up between himself and the champion, "Hollywood" Hulk Hogan. As President, Flair, with his son, David, made a match for Souled Out '99 against Barry Windham & Curt Hennig, which the two Flairs won with the help of Arn Anderson's tire iron. But Hogan and the rest of the nWo came out and attacked the Flairs, beating on David while holding Ric back. Next, during a Monday Nitro, David Flair defeated Bischoff (with help from Randy Anderson giving him a roll of quarters), allowing Ric to stay the President for life. This also got Bischoff's head shaved, which made Hogan angry. Subsequently, Hogan and Flair were signed to face each other for the World Title at the next PPV, Superbrawl IX. But at the PPV, Ric was betrayed by his own son, who zapped him with a cattle prod, enabling Hogan to get the pin. David had apparently been seduced by Torrie Wilson into betraying his father. This started Flair down a dark road...
The next month had the IV Horsemen and the nWo Wolfpac attacking each other, including a beating on Flair by most of the nWo. At Uncensored '99, Flair made a First Blood Cage Match with Hogan for the World Title. At the PPV, Hogan seemed to have the win, making Flair bleed after scraping his face with barbed wire. The referee, Charles Robinson, ignored the wound. After Arn Anderson took out David Flair, who was at ringside, Ric Flair put on the Figure Four leglock, getting the surprising win and regaining the WCW World Heavyweight Title, as well as still being the President of WCW.
Once becoming the champion, Flair became more and more of a "Bischoff" lookalike, making matches and always having his crooked friend, Charles Robinson, as the referee. Flair started to insult the fans again, and helped to turn the IV Horsemen, once again, into one of the biggest heel groups in professional wrestling. Flair also became involved in multiple feuds, which came to a head at Spring Stampede '99, when Flair had to face Sting, Diamond Dallas Page, and Hollywood Hogan in a Four-Way match for the World Title. Flair was pinned by Diamond Dallas Page, losing the title.
In late April '99, Flair began pulling bigger and bigger stunts as the President, signing papers without reading them and calling himself the President of the USA sometimes. This caused "Rowdy" Roddy Piper to get a few items signed, including committing Flair to a mental hospital, taking him out of action. After a brief time spent in a mental ward (where he ran into Scott Hall), Flair returned to face Piper for the Presidency of the company at Slamboree '99. Although Piper dominated the match, since "L'il Natch" Charles Robinson was the ref, Flair was given the pinfall victory after a foreign object shot. However, Eric Bischoff reappeared and came to the ring, telling Flair that Piper had won the match, apparently making Piper the President. But Flair disputed this call, claiming that Bischoff didn't have the power.
For the next month, the feud between Flair and Piper continued, and they agreed to a rematch at the Great American Bash '99, with the Presidency on the line once again. During the match, Flair got the Figure Four on Piper. Buff Bagwell then came out to help, attacking Flair and giving him the DQ win. Bagwell had been promised "the ball" by Piper if the Rowdy One won. However, after the match, Piper surprisingly sided with Flair against Bagwell, beating him. Flair then made Piper the Vice President of WCW. Flair soon became the leader of the more 'established' wrestlers, facing the tide of the youth movement, led by Buff Bagwell. Chris Benoit and Dean Malenko, two of Flair's former Horsemen, sided with Bagwell against Flair & Arn Anderson. Flair in turn brought in Diamond Dallas Page, Bam-Bam Bigelow, and later Kanyon to his group. The two groups battled for a few weeks, but nothing came out of it.
Soon, Flair and Page had a 'disagreement' that led to them breaking apart as a group. Page joined with Sting and "The Total Package" Lex Luger, both of whom had turned heel. Flair came out to protest what Sting and Luger were doing, and was viciously beat as a result. So Flair joined up with Hulk Hogan and Bret Hart against the force, going to war with Diamond Dallas Page at Halloween Havoc '99 in a Strap match that turned very ugly. During the match, Page's allies attacked both Flair and his son, David (who had reconciled, in an insane sort of way, with his father), getting Page the victory. Flair was out of wrestling for a while afterwards, as David fought his battles for him, facing Kimberly Page, and then DDP, in successive PPVs, while Ric Flair recuperated, among other activites. One of the most (in)famous moments of October was when Ric Flair, taking his son's place in a hotel room, surprised Kimberly, who had given David the key in hopes of drugging him. Whatever went on in the room did not go to air.
In the year 2000, Ric Flair again returned to his heel ways, joining with Luger to form "Team Package". While having short battles with guys like Sting and Hogan, Flair also renewed an old war, going at it with "the Commissioner" Terry Funk. In a Texas Death Match which was very brutal, Flair, with some help from his allies, defeated Funk at Superbrawl X. Soon after, Flair began a serious war of words and fists against Hulk Hogan, his long-time nemesis. When Hogan challenged Flair to a Yapapa Indian Strap match at Uncensored '00, Flair accepted. The two met in another brutal match, this time with Hogan coming out successful, despite Team Package's best efforts. Hogan and Flair then killed their feud quickly, as a major change was on the horizon for WCW.
In April '00, Vince Russo and Eric Bischoff returned to the fold, taking over the reins of WCW. They formed a group of the younger wrestlers, calling them the New Blood. Flair, along with Hogan, became a focal point for the New Blood, as Russo immediately began calling Flair out. Flair became one of the 'leaders' of the Millionaires' Club, along with Hogan, Luger, Diamond Dallas Page, Sid Vicious, and other established stars. Team Package, still united through the change, were put in the tag-team tournament for the vacated belts, against all the New Blood had to offer. Despite defeating the Mamalukes and the Harris Boys, Flair and Luger were unable to get past Buff Bagwell & Shane Douglas in the finals, at Spring Stampede '00, mostly due to New Blood trickery.
In anger over what had occured, Flair began a long-awaited feud with Shane Douglas, who had been calling Flair out for years (back in the days of Extreme Championship Wrestling). The two went to war at Slamboree '00, with Russo continuing to aid Douglas. But the true difference came when David Flair returned to the scene, betraying his father (once again) and causing him to lose the match. This began another dark time in Flair's family life. Ric came to the next Nitro, pleading for David to come with him, to straighten things out. But Russo continued to fill David's head, saying that, since Ric neglected David throughout most of his life, Russo was now his father. The battles between Ric and the New Blood continued, with many mind games being played by Russo & David Flair.
This did not stop Flair from adding onto his record. After winning a Battle Royale that made him #1 Contender to the World Title, Flair faced off against Jeff Jarrett. In a shocker, Flair rolled up Double J to win the WCW World Title for yet another reign. However, at the next Thunder, after a tag match, Flair collapsed. It was diagnosed as an inner ear problem, but it also had many concerned for Flair's health. During Nitro the next week, Russo 'stripped' Flair of the belt for health reasons, and gave it back to Jarrett. This lasted but a few days, as Kevin Nash defeated Jarrett for the belt, then gave it back to Ric Flair free and clear. Unfortunately, Flair's run with the belt this time lasted less than a day, as, at the same show, Flair was triple-teamed by Russo's regime, losing the belt back to Jarrett despite his best efforts.
Flair continued to fight against Russo and his son, including an epic battle inside a Hell in a Cell. Russo and Flair fought all over, with David Flair appearing inside the cage to help. Russo even climbed onto the roof through an escape hatch in the ceiling, only to be shoved back through the hole by Ric. The match ended with a splash of New Blood Paint, leaving Ric pinned while in David Flair's figure-four. Ric and David signed to face each other at the Great American Bash '00, father vs. son, with the stipulation that, if Ric lost, he would be forced to retire from the sport of wrestling. During the battle, Russo managed to get a pair of handcuffs on Ric, giving David many openings. But Ric's other son, Russ, and his daughter, Ashley, played a key role, and Ric came back, putting the handcuffs on Russo, then making his own son submit to the Figure Four, winning the match. However, the next night on Nitro, Ric wrestled Russo with the same stipulations in place. Russo used trickery and the power of the New Blood to take out Flair, thus "retiring" him.
Flair came back a few months later, not as a wrestler, but as the new Chief Executive Officer of WCW. He continued to make his presence felt for the next few months, usually countering "Commissioner" Mike Sanders during the Natural Born Thrillers' battles with the InSiders, Kevin Nash & Diamond Dallas Page. Flair seemed to have it in for the heels of the company, including "Big Poppa Pump" Scott Steiner.
At the beginning of 2001, Flair began having a "mystery man" launch assaults on Steiner, Jeff Jarrett, and other heels. This led up to WCW Sin, where the mystery wrestler was put into the main event with World Champion Steiner, Sid Vicious, and Jarrett. It all turned out to be a swerve, though, when the "mystery man" was revealed to be Road Warrior Animal, Flair's new bodyguard, who helped Steiner win and retain the title (this was the match where Vicious horribly broke his leg while attempting to come off the turnbuckle, prematurely ending the match).
Flair's group soon became known as the Magnificent Seven, consisting of Scott & Rick Steiner, Jarrett, Lex Luger, Buff Bagwell, Animal, & Flair. With Flair in charge of WCW as the CEO, his group became the most destructive since the nWo, doing whatever they wanted. Flair had a minor feud with the "Commissioner" at the time, Ernest "The Cat" Miller. But Miller voluntarily gave up his Commissionership to go after Kanyon, giving Flair all the power. However, Flair wasn't without enemies. At one Nitro, Flair brought Dustin Rhodes out and tried to give him a contract, to get him to sign with Flair's group. Rhodes instead cursed Flair out and attacked him, until Animal came out to double-team him. Enter Dusty Rhodes, Flair's long-time nemesis, who helped his son clear the ring. This led to a protracted feud between Flair and his partner, Jeff Jarrett, against the Rhodes. After a long build-up, the two forces were scheduled to wrestle at WCW Greed, Flair's return to the ring. During the night, Dusty was shown with 240 burritos, and said that he was going to make Jarrett & Flair kiss his ass. During the match, both Flair & Jarrett got Figure-Fours on the Rhodes, but both broke free. Dustin rolled up Jarrett to get the victory. Flair then ran from the ring, avoiding the stinkface, which allowed Jarrett to get it from Dusty instead.
The next night, on Nitro, Dusty said that Flair had only postponed the inevitable, and said that Flair had to kiss his ass. He again showed the burritos to be eaten as well. Later that night, Flair & Jarrett came out, with Flair saying that he wasn't going to kiss any ass. The Rhodes then came out, bringing with them a donkey named "Silver Dollar", aka, an ass. Dusty told Flair that he had to kiss it. Flair wanted to make Jarrett do it, but Jarrett refused. The two men then brawled with Dusty & Dustin, but were ultimately both forced to pucker up to the mule.
Soon afterwards, it was announced that Vince McMahon had bought WCW, and that the Season Finale, on March 26th, 2001, would be the last show under Ted Turner's ownership. Flair came out at the beginning of the Season Finale and talked about all the great superstars that had passed through WCW's doors. Flair then said that he wanted to go out with a bang, and called out Sting, one of his greatest foes. Sting reappeared later in the show, saying that he wouldn't miss it for the world. Flair and Sting went at it in the main event, showing the fans one last time what WCW had been all about. In a classic match that went back and forth, showing off every signature move of the two superstars, we saw wrestling personified. In the end, Sting got on the Scorpion Deathlock, and Flair tapped. After the match, both men embraced, letting loose the emotion of the moment.
At the '01 Survivor Series, Vince McMahon's WWF team managed to defeat Shane & Stephanie McMahon's WCW/ECW Alliance team in an "Elimination" Match, with Kurt Angle betraying the Alliance to help the Rock pin "Stone Cold" Steve Austin. On the next Raw, which was held in Charlotte, North Carolina, Vince McMahon was all smiles, punishing many former Alliance members in several ways (including having William Regal kiss his backside). At the end of the night, McMahon came out to the ring with Angle and the WWF World Title. McMahon talked about how Austin, the champion, had not shown up to do it personally, but that he was still going to strip him of the title and give it to Angle, whom he thought deserved it. However, McMahon was interrupted by Ric Flair's music! The Nature Boy walked out to a huge explosion from the hometown crowd. When McMahon demanded to know why Flair was there, Flair replied that he had bet on a winner, having bought Stephanie & Shane's WWF stocks beforehand. Therefore, since McMahon's team had won, Flair was now his partner as a co-owner of the WWF! Austin then came out and attacked Angle, reclaiming his WWF Title and drinking beers with Flair.
Although Flair and McMahon were equal partners, they frequently went at odds with each other over the next few months, as Flair played the "face" co-owner, while McMahon was the "heel". Flair sided with many of the top stars, including Steve Austin, the Rock, and Rob Van Dam, while McMahon had guys like Kurt Angle, William Regal, & the Undertaker on his side. On a December '01 Raw, when McMahon & Angle were set to face Trish Stratus & the Rock in a match (with the Rock having to kiss McMahon's backside if he lost), Flair added the reverse stipulation that McMahon would have to kiss the Rock's backside if their team lost. Thanks to Austin's interference, McMahon's team fell, leaving McMahon to have to pucker up to the Rock on the next Smackdown in order to save Angle's title shot at the pay-per-view (McMahon actually ended up kissing Rikishi's behind instead, which was far worse).
At Vengeance '01, Chris Jericho, with help from Vince McMahon, won the first Undisputed Heavyweight Championship (a unification of the WWF and WCW World Titles). During Jericho's final match with Steve Austin, Flair and McMahon got into it, with McMahon getting the better end of the brawl. On the next Raw, Flair, true to his word, handed Jericho the two titles, giving him his moment in the spotlight. Right afterwards, though, Flair announced that Jericho would have to defend the Undisputed Championship that night in a "Steel Cage" Match against Austin (Jericho retained due to Booker T's interference). For the rest of the year, Flair continued to place Jericho in title situations, while also feuding with McMahon.
On the last Smackdown of the year, Mr. McMahon came out and started telling all of his New Year's resolutions, including becoming more powerful than ever before. He was interrupted by Flair, who went on a long tirade about McMahon's recent actions. Flair also brought out a contract that he had discovered, showing the name as "Vince McMahon - Owner/Wrestler". This meant that Flair had the power to put McMahon in a match, so he scheduled McMahon vs. Flair at the next pay-per-view!
Animosity was high between the two owners going into the new year. On one Raw, McMahon embarrassed Flair, first by wearing a Flair wig and robe, then by knocking out Flair with a lead pipe when Flair came down to the ring. McMahon talked about how he loved to abuse his power and destroy lives. Flair came back by abusing his own power, making the match at the PPV a "Street Fight", with no disqualifications, no countouts, and no rules. At the '02 Royal Rumble, Flair and McMahon met up in their brutal match. The fight quickly went to the outside, where Flair was bloodied. McMahon added insult to injury by grabbing the camera from Megan Flair (Flair's daughter) and taking a picture of her father being beaten up. McMahon then tried to win with the Figure Four, but Flair reversed it, causing McMahon to go for a lead pipe. This backfired on him, though, as Flair got a low blow in to take the momentum away. Flair then took McMahon to the outside, smashing him into a monitor and cutting him open. Flair then demanded to see a replay of the hit on the very monitor he was watching! Flair also headed back to his daughter, having her take a very different picture, before taking McMahon back into the ring. Flair nailed McMahon in the head with the lead pipe, then put on the Figure Four, forcing McMahon to tap out and getting Flair a huge victory.
Flair came out to celebrate with the crowd on the next Raw, talking about how good it felt to win. He was interrupted by McMahon, who got into the ring as if to fight, but then opted to leave instead. McMahon then talked about how he wasn't the only one that had lost, that everyone in the WWF had lost. On the next Smackdown, in several dark segments, McMahon revealed how much the loss to Flair had caused him. He said that Flair had brought a "terminal cancer" to the WWF, but only he would be allowed to destroy his creation. So he would inject a lethal dose of poision into the WWF. He would bring in the new World order.
Flair confronted McMahon about the decision a week later on Raw, asking him not to destroy his own company. McMahon replied that the only way he wouldn't bring in the nWo would be if Flair gave up his half of the WWF stocks. After a few days' thought, Flair seemed to agree to the terms, coming out and saying goodbye to the crowd on Smackdown, that he had to think of the fans in this instance. McMahon arranged for the transfer to occur in the ring later that night, insulting Flair and calling him a loser, among other things. When Flair came out, he seemed to be having second thoughts, as the fans chanted for him not to sign. After hesitating, Flair began to sign his name, but was interrupted by "Stone Cold" Steve Austin, who came out and asked the fans to give a "Hell Yeah" if they wanted Flair to rip up the contract. The fans, of course, agreed, even as McMahon tried to get a cheap shot on Flair. Flair blocked it, then struck him back, allowing Austin to get the Stone Cold Stunner on McMahon. Flair then ripped up the contract, staying the 50% owner of the WWF.
Although Flair seemed to second-guess his actions later (especially after Arn Anderson was quoted as saying he made the wrong decision), he stood by what the fans wanted, even as McMahon announced that the nWo would be returning at the next pay-per-view. Flair also started to have problems with the Undertaker. After the Dead Man savagely beat down the Rock, injuring him, Flair confronted the Undertaker about it, with the two having words. Flair set the Undertaker to face the Rock at the next PPV, and also placed the Undertaker into a match with "Stone Cold" Steve Austin that night (the match ended in a DQ when Chris Jericho attacked Austin). At No Way Out '02, during the Undertaker/Rock match-up, the Dead Man took out the referee, then went for a lead pipe on his motorcycle. Flair then came out to stop him, with McMahon appearing later to try to go after the Rock. In the end, Flair nailed the Undertaker with the lead pipe, allowing the Rock to get the Rock Bottom for the pinfall victory.
The Undertaker came into Flair's office on the next Raw with a challenge to the Nature Boy, saying that he wanted to face Flair at Wrestlemania. Flair, though, surprisingly declined the challenge, saying that he wanted to focus on being an owner, not a wrestler. The Undertaker didn't take this news well, saying that he would change Flair's mind. Over the next few weeks, that's what the Undertaker did. On one show, the Undertaker took out Arn Anderson, brutally bloodying him in the ring. Later, the Dead Man went down to Ohio Valley Wrestling and destroyed Flair's son, David, trashing him in a bathroom. Flair then agreed to the match with the Undertaker, but the Dead Man didn't want just an acceptance. He called Flair out to have him beg for the chance to face him. Flair refused, though, instead attacking the Undertaker in a wild brawl. During the fight, a fan was hit at ringside, leading to Flair being arrested and taken away, while the Undertaker was seen with a big smile on his face.
McMahon quickly used the arrest to his advantage, calling Flair into a Board of Directors meeting to question his actions in front of Linda McMahon and the rest of the Board members. McMahon talked about how Flair's actions were unbecoming of an owner. Flair, when asked, barely defended himself, saying that he had to do what he did because he had his pride. The Board later temporarily took away Flair's power, giving it to McMahon, who quickly used it the Smackdown before the pay-per-view, first giving Flair the night off, then bringing David Flair up to Smackdown for one night only, to face off against the Undertaker. The match was short-lived, as David Flair was quickly being dominated by the Dead Man. Ric, though, came out to help his son, and ended up causing the DQ by nailing the Undertaker with a violent chair shot, sending him out of the ring.
At Wrestlemania X-8, Flair and the Undertaker went at it in a brutal "No Disqualification" Match. The fight quickly went to the outside, as the two men fought around the announcers' table. The Undertaker took control by throwing Flair into the ringpost, then dominated for a time, cutting the Nature Boy open. Every time Flair started to make a comeback, the Dead Man stopped it, getting in more offense. Flair finally started to make a comeback when the Undertaker missed a big boot, doing the splits on the top rope. Flair knocked him out of the ring, then followed, getting the Undertaker's lead pipe from his motorcycle and using it to bloody the Dead Man up. The momentum shifted a few more times, leading back into the ring, where Flair got the Figure Four applied. But the Undertaker was able to reach over and grab Flair by the throat, breaking the hold and lifting the Nature Boy in the air for a Chokeslam for a 2 count. This led the Undertaker to beat down the referee (Charles Robinson), but this just led to Arn Anderson running out and getting the Spinebuster on him. But despite the double-team, the Undertaker was just too strong, throwing Arn from the ring, then Tombstone Piledriving Flair for the 3 count.
WWF Raw: 2002
On the Raw following the pay-per-view, Linda McMahon made the surprise announcement that, a week from that night, the WWF would split into two shows. Flair would be 100% in charge of Raw, while McMahon would be 100% in charge of Smackdown. McMahon won the coin toss that night, meaning that he would get to draft from the current roster first. McMahon also tried a sucker punch on Flair, but it backfired, as Flair came back and took McMahon down for the Figure Four. The next week, McMahon and Flair selected their picks, with Flair surprisingly taking his Wrestlemania foe, the Undertaker, with the first pick. Flair followed that up by selecting the nWo (Hall/Nash/X-Pac), Kane, Rob Van Dam, Booker T, the Big Show, Bubba Ray Dudley, Brock Lesnar, William Regal, and Lita for his on-air picks. Flair and McMahon later went into a 'bidding' war for "Stone Cold" Steve Austin, who had had a "No-Draft" Clause in his contract. Flair won Austin's signature on the contract when Austin Stunned McMahon, but Austin followed it up with a Stunner on Flair as well, leaving both men out.
Flair also continued to have problems with the Undertaker. The Dead Man had challenged Triple H for the Undisputed World Title, and Flair had sanctioned the match at the PPV. But Vince McMahon, on Smackdown, overruled Flair, saying that, as the man who won the coin toss, he got to choose the challenger for the first PPV, taking away the Dead Man's shot. Instead, Flair set up two #1 Contenders Matches, with the Undertaker beating Rob Van Dam and Austin beating Scott Hall to earn a shot at the shot, a #1 Contenders Match at the next PPV. During the Austin/Hall match, the Undertaker came down to interfere, with Flair coming down as well to try and stop it. Austin finished off the match by Stunning everyone, including Flair once again. On the next Raw, Flair came out at the beginning of the show and called out Austin, saying that he had warned Austin about putting his hands on the boss, and fined him $5,000. Flair claimed that he had nothing against Austin, and wanted him to beat the Undertaker at the PPV. Austin, meanwhile, said it was Flair's own fault for being at ringside, and that he had never asked for Flair's help. The Undertaker then came out and threatened both men, causing Flair to announce that he would be the special referee between the two men!
Before the match at Backlash '02, Flair had a confrontation with Vince McMahon. McMahon mentioned Flair's recent problems with Austin, and said that he was starting to relate to Flair. Flair responded by saying he would never be like Vince McMahon, to which McMahon replied, no, but you can try. In the match, Flair tried to be an impartial referee for Undertaker vs. Austin. He also had to worry about the nWo, who came out to the ramp to 'watch' the match. During the bout, Flair was knocked down when Austin shoved the Undertaker into him. Soon after, Austin got the Stone Cold Stunner, but Flair couldn't make the count. Flair recovered enough to make a 2 count for the Undertaker's Chokeslam, but then denied the Dead Man the use of a chair. Flair then went down again, this time when Austin ran into him, allowing the Undertaker to regain the chair and use it on the Rattlesnake. Near the end of the match, Austin tried to use the chair on the Undertaker, but Flair grabbed it. Austin pulled it free, but the Undertaker was able to kick it into Austin's face, then made the cover. Although Austin got a foot on the ropes, Flair didn't see it, counting to 3 and giving the Undertaker the #1 Contender's spot. Afterwards, in the back, the Coach pointed out to Flair that he had missed the leg. Flair, upset, cursed and walked away.
Twenty-four hours later on Raw, Flair apologized for his mistake, and again claimed "I'm not Vince McMahon". Austin confronted him in the ring, saying that at least McMahon didn't lie to his face. Flair, wanting to make things right, blamed the nWo for distracting him during the match, and put Austin & Bradshaw in a match with them. But Bradshaw was taken out before the match. Flair substituted in the Big Show to be Austin's partner, but this all turned out to be a swerve, as the Big Show, after being tagged in, Chokeslammed Austin and joined the nWo. A week later, Flair, claiming to know nothing of the Big Show's turn, made himself the referee for a rematch between Austin & Bradshaw and the nWo (Hall & X-Pac). Austin's team won after a Stunner, when Flair counted to 3 despite X-Pac's leg being on the rope. The nWo threatened Flair later on, with Flair standing his ground. It was during this time that Insurrextion '02 took place in England, where Flair made himself the special guest "second" referee in a match between Austin and the Big Show. Flair kept the nWo at bay to allow Austin to get the win, but Austin landed a Stunner on Flair afterwards.
WWE Raw: 2002
It was announced at the next Raw that the WWF had become World Wrestling Entertainment (due to a lawsuit with the World Wildlife Fund). For the "new" show, Flair set up a match to have himself, Austin, & Bradshaw take on Hall, X-Pac, and the Big Show (who had apparently returned from a tour of India). Hall, in an interview, promised a major surprise during that match. Flair, seemingly concerned about the surprise, checked the nWo locker room and Bradshaw's locker room, finding an APA hat and Kane's mask (which had been stolen by X-Pac) respectively. Flair confronted Bradshaw about it, wanting an explanation, but Bradshaw refused, saying that he & Austin were heading to the ring. During the match, the suspicion hung between Bradshaw and Flair, but it was actually a swerve, as Flair turned on Austin, nailing him with several chair shots! Flair then told a battered Austin that he would be facing the Big Show & Flair at the next PPV in a Handicap Match!
Flair continued to abuse his power at the next Raw. First, he informed the nWo that he had to fire Scott Hall, apparently because of his problems beating Austin (actually, it was because of Hall's alcohol problem). Next, Flair booked himself in the main event, facing Hulk Hogan for the Undisputed Championship. But the match broke down after interference by the nWo, Bradshaw, and finally Austin, who hit the Stunner on Flair, knocking him down for Hogan to get the Leg Drop and win the match. Furious afterwards, Flair put Bradshaw in a Handicap Match against X-Pac & the Big Show (which the nWo won) and Austin in a "Lumberjack" Match against the newest member of the nWo, Booker T. Austin won the match after miscues from Booker T & X-Pac, but didn't get away unscathed, as Arn Anderson surprisingly came out of the back and took him down long enough for the rest of the nWo to get at him, bloodying him with a savage beatdown.
At Judgment Day '02, Flair had another chance meeting with Vince McMahon. This time, the two shook hands, as Flair told McMahon he was right in saying that Austin was a no-good son-of-a-b****. Flair promised to take Austin down, then gave a surprised Vince a hug. The match between Flair & the Big Show and Austin started quickly, with a furious Austin assaulting both men. He then tried to bring a chair into the ring, but the referee (Charles Robinson yet again) wouldn't let him. Austin quickly showed his displeasure, sitting down in the chair and flipping off Robinson. Austin seemed to have Flair's number, but the Big Show's power brought their team back into control. Flair & the Big Show worked over Austin's legs, damaging them so that Flair could use the Figure Four to full effect. Austin refused to tap, though, eventually reversing the hold (with the Big Show breaking it up). In the end, after an Austin Stunner on the Big Show, interference from X-Pac backfired, as he accidentally kicked the Big Show. Austin then Stunned X-Pac and then Flair, then pinned the owner, winning the Handicap Match.
Flair came out with Arn Anderson on the next Raw, saying that the loss didn't count, since the Big Show, not Flair, was the legal man. Flair then called out Austin, telling him that he was going to Plan B, namely, that Austin was benched and wouldn't be competing. Austin responded by Stunning both Flair and Anderson and drinking some beers. On the last week of May '02, Chris Benoit (who was drafted for Smackdown) appeared on Raw, since it was in his hometown, and he wanted to see the fans. Benoit and Eddie Guerrero then had a confrontation, with Flair breaking it up by having security throw out Benoit (since he wasn't with Raw). Later in the night, Rob Van Dam defeated Guerrero to win the Intercontinental Title. After the match Guerrero attacked RVD with the ladder, prompting Austin to come out and go after Guerrero (who had bashed Austin with a beer bottle on the previous Raw). Flair & Anderson ran out to aid Guerrero, with Benoit apparently coming out to help Austin. But Benoit attacked Austin from behind, leading to a four-way beatdown, with Benoit laughing alongside Guerrero, Flair, & Anderson.
A week later, Flair came out with Benoit & Guerrero, with Benoit explaining that, since it had been Austin who had put him on the shelf for almost a year with injuries, he was just getting some payback. Flair also reiterated that Austin was not going to wrestle. But Austin came on the TitonTron, showing that he had captured Anderson, and wouldn't let him go unless Flair agreed to a match with him (since Guerrero already had a match and Benoit was not medically cleared). The stipulations would be that if Austin won, he was off the bench, while if Flair won, Austin wouldn't wrestle again. Flair agreed, even as Austin decided to urinate on Anderson. Flair later jury-rigged the contract, having it state that if he won, Austin would be his personal assistant, and that Austin couldn't use punches. The attorney messed up slightly, though, leaving the personal assistant stipulation available for either wrestler. Despite being unable to punch, and despite the interference at one point from Benoit & Guerrero, Austin won the match with a Stone Cold Stunner, making Flair his personal assistant. Or so it seemed.
On the next Raw, Flair showed up at the beginning of the show to state that Austin had failed to show up that night (a real-life story; Austin "took his ball and went home"). Flair then had a verbal sparring match with Vince McMahon, ending up with the two men deciding to go at it in a "No Holds Barred" Match, with the winner getting full control of both shows. Flair and McMahon had another brutal war against each other, using any and all weapons they could find. With Arn Anderson watching from ringside, Flair seemed to have control in the final minutes, eventually getting McMahon in the Figure Four Leglock. But Brock Lesnar then surprisingly came down the aisle and attacked, giving Flair the F-5. Strangely, Anderson chose to leave rather than help, allowing McMahon to get the pinfall and win the match, taking away Ric Flair's ownership of Raw.
A week later, Flair came out talking about how he had decided not to just go home like Austin did, and signed a WWE wrestling contract. He was then cursed out by Guerrero, who saw his departed chance to fight Austin as Flair's fault. Benoit then came down, apparently to defend Flair, and even flashed the IV Horsemen sign. But Benoit then said that he, too, blamed Flair for losing his chance for revenge on Austin. The two men beat down Flair, with Guerrero using the Figure Four on him. At King of the Ring '02, Flair and Guerrero had it out, with Guerrero mocking Flair from the very beginning. Guerrero even used Flair's Figure Four on him again, with Flair able to escape. Later on, when Guerrero missed a Frog Splash, Flair applied his own Figure Four, nearly forcing Guerrero to tap. Later on, though, after Guerrero tossed Flair from the ring, Benoit appeared and struck, putting Flair in the Crippler Crossface. This backfired on Guerrero, though, as, while the referee, who had turned and seen Benoit at ringside, was telling him to leave, Bubba Ray Dudley came in out of nowhere and Bubba Bombed Guerrero. Flair then made the weak cover, as the returning ref counted to 3 and gave the win to the former owner.
A few weeks after the PPV, the 2002 King of the Ring, Brock Lesnar, with his manager, Paul Heyman, at his side, called out a veteran from the back, as he wanted to prove how great he was. Flair's music hit, and the Nature Boy walked out, saying that he hadn't forgotten that Lesnar had cost him the co-ownership of WWE. Flair and Lesnar had a good match, with Flair nearly winning with the Figure Four. But after being distracted (and swinging at) Heyman, Flair was caught with the F-5 and pinned, losing to the young star. A week later, Flair was seen in the back advising Jeff Hardy for his European Title match. He was overheard by Steven Richards, who talked about how Flair's legendary status had dropped as of late. Flair quickly told Richards to back up his words, and showed him why he's the Nature Boy later on that night, making Richards submit to the Figure Four.
Flair had a shock to his system in the middle of July '02, as Eric Bischoff was surprisingly announced as the new General Manager of Raw. Flair and Bischoff had a short confrontation in the back, with Bischoff wanting to put the past behind them. Flair didn't seem to see it that way, as he walked away to prepare for his match. Later on that night, Flair teamed up with Rob Van Dam to take on Brock Lesnar & the Undertaker. While Flair & RVD seemed to work well together, they were facing too much power, as the Undertaker took out RVD with the Last Ride to get the pin. That Sunday, at Vengeance '02, Flair didn't compete, but was seen in the back congratulating Jeff Hardy on his European Title defense over William Regal along with Hulk Hogan.
For the next few weeks, Flair seemed to be a mentor for Hardy, encouraging him in his win streak while criticizing Bischoff for constantly putting Hardy into "hardcore" situations. On the last Raw of July '02, Flair was given a "Non-Title" Match against the Undisputed Champion, the Rock, who was thrilled to have had matches against both Hogan and Flair that year. Flair gave the Rock a good competition, even locking in the Figure Four at one point, but the Rock won out with the Rock Bottom, then shook Flair's hand afterwards. After the Rock had left, Flair got on the mic, wanting to make a special announcement (presumably his retirement). However, before he could, Chris Jericho's music came over the 'Tron, stopping him. Jericho then appeared behind Flair, knocking Flair out with a chair shot before announcing that Raw Is Jericho (he had been on Smackdown). Flair got revenge the next week, as he smacked Jericho with a chair shot of his own, helping Rob Van Dam beat Y2J.
Flair and Jericho continued to feud for the next few weeks leading up to Summerslam '02, with Flair interrupting Jericho's band, Fozzy, at one point to get a piece of Y2J. At the pay-per-view, the two men had their match, with Jericho still talking about how much of a has-been Flair was. Jericho seemed to be much stronger early on in the match, shaking off Flair's knife-edge chops and taking control for a long while. Flair finally started to make a comeback after a Jericho miscue, concentrating on Jericho's back. Jericho responded, though, with a version of the Figure Four, with Flair barely able to make it to the ropes. In the end, with the referee (again Charles Robinson... coincidence or conspiracy?) distracted, Flair got a low blow on Jericho, then locked on his own Figure Four, forcing Jericho to submit.
At the beginning of September '02, when Brock Lesnar decided to make the WWE Undisputed Title exclusive to Smackdown, GM Eric Bischoff opted to award a new WWE Raw Heavyweight Title to Hunter Hearst Helmsley. Flair then came out, upset at how a belt he had worn so many times was not being earned. Flair then challenged Triple H to a match, with Triple H accepting it. Bischoff made the match, even as Triple H nailed Flair with a sucker-punch. Backstage, Flair had another confrontation with Jericho, who couldn't believe that Flair was getting a title shot in front of him. Jericho said he wanted Flair to win, though, so that he could beat him and get the belt. In the match, Flair and Triple H both fought hard, exchanging the momentum several times. In the end, though, after the referee had to go outside to dodge a hit, Triple H scored a low blow followed by the Pedigree, winning the match. Afterwards, Jericho ran out to the ring and put Flair in the Walls of Jericho, with Rob Van Dam making the save. This led to a match signed for the end of the night, with Flair & RVD winning a tag match over Jericho & Triple H.
Flair continued to support Van Dam, cheering him on when RVD won a #1 Contenders Match on Raw. A week later, Flair got a match himself, but was surprisingly upset by a young gun, Rico. In the back after the match, Triple H talked about how pathetic a loss it was, and told Flair he should retire. Flair responded by saying it was more pathetic that Triple H was wearing a belt he hadn't earned. Later on that night, thanks to Triple H's interference, Jericho won the Intercontinental Title from Van Dam, then told Bischoff that he wanted to defend the belt against Flair at Unforgiven '02 in a rematch from Summerslam. The match was another good one, with Flair looking to get his first WWE gold since 1992. Near the end of the match, Jericho went down holding his leg, stopping the action. But it was a ruse from Y2J, who suddenly got up and caught Flair in the Walls of Jericho, forcing him to tap out and winning the match. Later on that night, Flair came out during the RVD/Triple H World Title match, as the referee was down. Flair grabbed Triple H's sledgehammer, apparently to use it on the champ. But instead, Flair surprisingly turned around and nailed RVD, much to the surprise of both men. Triple H quickly took advantage of the situation, though, Pedigree'ing Van Dam to win the match.
Flair came out on the next Raw to talk about what happened, saying that he agreed with many of the comments that Triple H had made about him in recent weeks. Flair said that he wanted to take Triple H to a whole new level, while ending his career by his side, on top of WWE. Van Dam then came towards the ring, but Triple H attacked him from behind, leading to a double-team, with Bubba Ray Dudley making the save. This led to a tag-team match between the four men, with Flair getting the win by rolling up Bubba and holding his tights. After the match, though, Van Dam & Bubba got revenge by putting Triple H through a table. Flair cotninued on the track as Triple H's manager over the next few weeks, helping the Raw World Champ continue to rack up victories. He also sided with Triple H in his feud against Kane, which included announcing about how Kane had apparently 'killed' his old girlfriend, Katie Vick (a storyline best not remembered).
At No Mercy '02, Flair had a match with the man he had betrayed Rob Van Dam. Despite Flair's best dirty tricks, he couldn't stop "Mr. PPV", who won out with the Five Star Frog Splash. Flair was still able, though, later in the night, to help Triple H stay the Raw World Champion over Kane. Twenty-four hours later on Raw, Flair joined with Triple H in humiliating Kane by showing a video "chronicalling" Kane (as played by Triple H) having sex with a dead woman (again, not worth remembering). Later in the night, Flair & Triple H took on Kane & Van Dam, with RVD once again pinning Flair after a Five Star Frog Splash. Flair, down and hurting, was then unable to help as Kane threw Triple H into the trunk of a car and drove off (with Triple H escaping from the trunk via a safety button). A week later, Triple H was scheduled to fight in a "Non-Title Casket" Match with Kane. Although Flair was expected to be a major factor on the champ's side, he called in and said his plane had been delayed, keeping him from the arena. Thus, no one was there to counter Shawn Michaels' interference, allowing Kane to put Triple H in the casket.
Flair managed to show up over the next few weeks, helping to prep Triple H for his defense of the Raw World Title at the next pay-per-view. At the same time, Flair began building for the future, as he was seen talking with Dave Batista, praising him for his power and strength. At the '02 Survivor Series, Flair had to watch from outside of the Elimination Chamber as Triple H wrestled against five other men. In the end, Shawn Michaels won out with some Sweet Chin Music, winning away the World Title. On the next Raw, an upset Flair informed Bischoff that Triple H, being injured, wouldn't be competing that night, and had in fact not shown up. Bischoff, apparently deciding on some retribution, placed Flair in a match against Kane. Flair came out for the bout dressed in a suit, saying that he wasn't going to wrestle. He told Kane that he respected him, but that if Kane laid a finger on him, he'd have to answer to Triple H. Kane, predictably, didn't care about the threat, and went after Flair, who ran away from him. As Kane gave chase, though, Batista appeared and knocked him down, showing that he had joined with Flair & Triple H.
On the next Raw, Kane demanded a match against Batista. Once again, Flair proved to have a pivotal role, as first he distracted Kane by coming out first so that Batista could get a sneak-attack, and later by hitting Kane with a chair shot while the ref was down, enabling Batista to get the Batista Bomb. Flair managed Batista the next week as well, watching as Batista defeated Kane's tag-team partner, the Hurricane. Later on that night, Flair tried to manage Triple H in his #1 Contenders Match against Rob Van Dam. But the special referee, the World Champ, Shawn Michaels, barred Flair from ringside. Helmsley was still able to get the win, though, which allowed Flair to continue to manage two strong stars.
In December '02, Flair stayed with both Batista & Triple H, helping both get impressive victories (usually because of a distraction from the Dirtiest Player In The Game). Flair also helped with the mind games, as he got under Shawn Michaels' skin by saying that, a few years ago, Flair had decided that he was no longer the man; Michaels was. But now Michaels was no longer the man, since he didn't have the body to keep up with someone like Triple H. Later on that night, though, Michaels proved his heart, taking out both Flair & Triple H in the parking lot. At Armageddon '02, Flair continued his cheating ways. First, his distractions helped Batista beat Kane. Then, at the end of the night, Flair proved to be a major factor in Triple H winning back the Raw World Title in a "3 Falls" Match over Michaels. Flair would finish out the year joining Triple H in his new feud against the former WCW World Champ, Scott Steiner, who had been given a World Title shot due to signing a contract with Raw.
At the '03 Royal Rumble, Flair once again sat in Triple H's corner, cheering on the champion as he faced the tough challenge of getting past Scott Steiner. It was a long match (with the crowd interestingly booing Steiner and cheering Triple H for some reason), with Flair doing all he could to cheat for his man. At one point, Flair grabbed the Raw World Title and Triple H and tried to steer him for the exit, content with a countout to preserve the belt. Steiner chased them down, though, and brought Triple H back to the ring. Later on, Flair screamed at the referee (NOT Charles Robinson, but Earl Hebner; guess the "Robinson coincidence" only pertains to Flair) to end the match via Triple H's blood loss, but the referee refused. It finally ended with Triple H using the sledgehammer on Steiner, ending the match via DQ. Afterwards, Steiner took out Flair, then held Triple H in the Steiner Recliner.
On the following night's Raw, Steiner came out and demanded a rematch for the title, but Flair & Triple H announced that the champ wasn't medically cleared, and instead arranged for Steiner to face Batista. During the night, Steiner had a confrontation with Randy Orton, who was returning from a shoulder injury. For the main event, Flair came down with Batista for his match with Steiner, but the match barely even got started before Orton appeared to attack Big Poppa Pump. Flair & Batista joined in, with Triple H coming down to help out as well. The four men eventually beat down Steiner, then raised each other's hands in celebration. This was the beginning of Evolution.
The four-man stable beat down Steiner again the next week, then assaulted Tommy Dreamer before one of his matches a week later. Triple H then got on the mic and talked about how if you don't have what it takes, then Evolution will leave you behind. The Evolution started with Flair (the past), ran through Triple H (the present), and went to Batista & Orton (the future). During the night, Batista & Orton electrocuted Goldust by throwing him into a power box. This led to Booker T joining with Steiner in battling Evolution. At No Way Out '03, Flair watched as Triple H again defended the Raw World Title against Steiner. At one point, when Triple H was trapped in the Steiner Recliner, Flair called for Batista & Orton to come down, distracting Steiner. Big Poppa Pump was able to fight off the 3 men, though, with the referee sending them from ringside. However, the distraction allowed Triple H to hit Steiner with the title belt, then get the Pedigree for the victory.
When Booker T won the #1 Contenders Battle Royal going into March, Flair and the rest of Evolution increased their feud with him, as he was the newest threat to Triple H's Raw World Title. Things seemed to get worse for Triple H's chances soon afterwards, as both Batista & Orton went down with various injuries. Still, Flair joined Triple H in making several derogatory and racist remarks towards Booker T, among them saying that he wasn't worthy to face Triple H, and that he should be carrying their bags. This, of course, led to several brawls between Flair, Triple H, and Booker T. On the last Raw before the pay-per-view, Flair & Triple H tagged against Booker T & Goldust. In a surprising ending, Triple H was the one pinned, after being knocked bloody by Booker T. Flair helped Triple H get his revenge, though, at Wrestlemania XIX, where Triple H beat Booker T via the Pedigree to stay the Raw World Champ.
Going into April '03, Flair & Triple H began teaming with Chris Jericho in their respective feuds with Booker T & Shawn Michaels. Michaels, though, had another surprise, as he brought back Kevin Nash, who seemed to side with HBK, although he and Triple H still appeared to have some chemistry from the "Clique" days (the Clique was a backstage group consisting of Helmsley, Nash, Scott Hall, Shawn Michaels, and somewhat of X-Pac). When asked Bischoff to "make a decision" about picking a side, Nash replied that he would be on his own. Triple H later made up Nash's mind for him, as, after Nash had helped him up after a match, Triple H gave him a low blow from behind. During this period, Flair also had a mini-feud with the Hurricane, attacking him after a match with Jericho and putting on the Figure Four.
At Backlash '03, Flair finally returned as an active wrestler on a PPV, having not competed since October '02. He teamed with Triple H & Chris Jericho against Nash, Michaels, & Booker T in a Six-Man Tag-Team Match. It was a solid match, with all six wrestlers showing off their various talents inside the squared circle. Near the end, when everything started to break down, the wrestlers paired off, brawling around the ring. While the referee was distracted, Nash went for the Jackknife Powerbomb on Jericho. After hitting the maneuver, though, Triple H came into the ring with his sledgehammer, knocking Nash out and getting Flair's team the big victory.
On the next Raw, Flair was informed by Triple H that it was time for the Nature Boy to have some gold around his waist. He explained that Bischoff had signed a Tag-Team Title Match between Flair & Triple H and the champs, Rob Van Dam & Kane. During the match, Shawn Michaels was shown in the backstage area, saying over the phone that Triple H was a sitting duck. Flair & Triple H, meanwhile, were working well as a team, with Flair even getting the Figure Four on Kane. RVD broke it up, though, with the Rolling Thunder, but Triple H was able to get rid of Van Dam and score the Pedigree on Kane. However, Nash then came out with a sledgehammer, sending Triple H running for it and leaving Flair in a handicap match. It didn't last long, as Flair tasted the Chokeslam and the Five Star Frog Splash before getting pinned, losing the chance to become a champion again.
A few weeks later, while protesting to "Stone Cold" Steve Austin about how Triple H should be in charge of the show (Austin had been named co-General Manager along with Bischoff), Flair was insulted by the Hurricane, who thought Nash was going to kill Triple H at the PPV. Austin, seeing the hostility between the two men, set up a match right then and there, and 'rang' the bell by saying "ding". Flair and the Hurricane brawled through the arena, heading towards the ring. At one point, Flair had his pants pulled down (since he wasn't in ring gear), an embarrassing moment, but the Nature Boy came back to beat the Hurricane with the Figure Four. Triple H came out afterwards and nailed the Hurricane with a Pedigree, adding to the damage. At Judgment Day '03, Flair watched (and interfered when possible) as Triple H defended the Raw World Title against Nash. The match ended badly, in a way, for Triple H, who got knocked out by the gold, but still retained it via a DQ win.
Twenty-four hours later on Raw, Flair & Triple H were called out by co-GM Austin, who said that Triple H would have to defend the title that night. Austin also said that Triple H could pick his opponent, as long as he was a former World Champion. Triple H, who was still sore from the beating he had taken from Nash, tried to outsmart Austin, by choosing Flair as his opponent, which was a complete surprise to Flair. Triple H seemed to think that Flair would lay down for him, basically giving him the night off. But Flair seemed strangely reluctant at the idea, especially after Shawn Michaels approached him in the back and talked about how Flair had set the standard in the business, and shouldn't lay down for anybody. Flair later agreed, telling Triple H that he wasn't going to give him the match without a fight. Flair and Triple H then had an extremely competitive match, with the fans getting behind the Nature Boy. Flair nearly won the match after a low blow and a title shot while the referee was down, but in the end, the champ won out with a Pedigree. After the cameras stopped taping, a crowd of WWE wrestlers came out out of character and praised Flair, including Vince McMahon and Triple H. Flair then gave a deeply emotional speech to the fans, thanking them for all they had done for him.
A week later, Flair came out with Michaels, as Michaels continued to praise Flair. HBK also challenged Flair to a friendly match, which Flair accepted. However, the two were interrupted by Triple H, who told Flair that he was the one who made him back into the Nature Boy, and to not turn on him. Flair responded by saying that he was standing alone from now on. Co-GM Eric Bischoff then came out and made the match between Flair and Michaels for the next PPV, while arranging for a "Handicap" Match that night, with Flair & Michaels going against Triple H. During the night, Flair was seen in the back, preparing for the match, with a masked man watching him from the doorway. During the match, Michaels took the brunt of the assault with Triple H, until finally making the hot tag to Flair. But the Nature Boy quickly punched out Michaels, showing that the whole thing had been a ruse. Kevin Nash then ran down to try to make the save, only to have a "3-on-1" assault, as the masked man appeared to help take him out. The man then removed his mask to reveal Randy Orton, back from his injuries to rejoin Flair & Triple H in Evolution.
Going into June '03, Flair, Triple H, & Orton made another statement at the beginning of Raw, beating down the Hurricane after he came out for a match. Flair then praised Triple H, saying that he had passed the torch to him, not to Michaels. HBK & Kevin Nash then came out, with Michaels saying that he would stick the torch where the sun didn't shine. As the two men came towards the ring, a recovered Hurricane joined them, sending Evolution out. The six men had a match later that night, with Triple H getting the win after a Pedigree on the Hurricane. At Insurrextion '03, Flair joined Triple H for his "Street Fight" Match with Nash (with Michaels in his corner). Within minutes of the match, Flair was a bloody mess, but he still helped Triple H win, keeping Michaels busy while Triple H used a sledgehammer to knock Nash out.
Only a week later, Flair wrestled against Michaels at Bad Blood '03. The match started out with the Heart Break Kid dominating, with Flair able to get the momentum back only through dirty tactics. Both wrestlers tried on a version of the Figure Four, with neither getting the other to submit. Flair also nearly got the win after a roll-up while holding the tights, but he couldn't keep Michaels down. Things started to get ugly as the fight went to the outside, where Michaels set up Flair on a table. Randy Orton then came down to try to make the save, but Michaels knocked him out with some Sweet Chin Music, then came off the top rope to splash through Flair (and the table), cutting up Flair's back. When the referee accidentally got low blowed, though, it began to change the momentum. Flair tasted some Sweet Chin Music, but Orton reentered the ring, bloodying Michaels with a huge chair shot. Orton then had a barely conscious Flair make the cover, getting the 3 count and the victory.
Flair joined with Randy Orton in feuding with Mick Foley & Maven on the next Raw, with Orton getting a win over Maven with the RKO, but Foley getting revenge with a Mandible Claw for both Flair and Orton. Flair & Orton tagged up the next week, but were beaten by Nash & Michaels, with HBK knocking out Flair with some Sweet Chin Music. After the match, in the back, Foley told a passing Flair & Orton "nice match". This led to the two Evolution members attacking Foley, and after a back-and-forth brawl, Orton kicked Foley down some stairs, injuring him. Flair & Orton later helped Triple H beat Kane in a "Mask vs. Title" Match, forcing Kane to unmask. Flair continued helping out Orton a week later, cheating to help him beat Tommy Dreamer. The two beat down Dreamer after the match. Flair & Orton then had another significant role in Triple H's match, a "No DQ, No Countout" win over Rob Van Dam. Van Dam got some revenge on the next Raw, though, teaming with Bubba Ray Dudley to beat Flair & Orton.
Evolution continued to do things their way as the WWE headed into August '03. Flair routinely interfered on behalf of Triple H and Orton in their matches, while occassionally wrestling himself. When Triple H began to feud with Bill Goldberg, Flair was placed in a match with Da Man. Goldberg dominated a lot of the match, which led to Orton hitting him with a chair, causing the DQ. Triple H joined the rest of Evolution for a beatdown of Da Man, with Shawn Michaels, Chris Jericho, and finally Kevin Nash all making run-ins. This led to co-GM Austin making a match at the coming PPV an Elimination Chamber match, with Triple H, Orton, Goldberg, Michaels, Jericho, & Nash involved. Flair had a rematch with Goldberg the next week, this time with Orton as the special guest referee. Despite that, Goldberg won again, with Michaels proving to be the equalizer.
At Summerslam '03, Flair & Orton could only watch from outside the Elimination Chamber as Triple H fought 5 other men for his gold. Fortunately for Evolution, Triple H won out, taking out Goldberg with a sledgehammer hit at the end. Afterwards, Flair & Orton entered the cage to celebrate with Triple H and beat down a handcuffed Goldberg. Evolution continued to feud with Goldberg after the PPV, as Triple H signed a rematch with him for Unforgiven, with the stipulation that if Goldberg lost, he would have to retire. On the first Raw of September '03, Evolution fought in a Six-Man Tag Match against Goldberg, Shawn Michaels, & Maven. Although Evolution did well against the other two, they couldn't stop Goldberg, who Speared and Jackhammered Orton to win the match. Evolution got its revenge the next week, though, thanks in part to co-GM Bischoff, who booked Flair & Triple H vs. Goldberg & Orton. Of course, this resulted in a 3-on-1 beating, with Triple H devestating Goldberg with a huge chair shot.
At Unforgiven '03, Flair first helped Orton in his match against Shawn Michaels. When Michaels seemingly had the victory, Flair stopped the count by putting Orton's foot on the ropes. Later on, Flair got Orton some brass knuckles, which he used to knock out the Heart Break Kid for the win. Things didn't go as well at the end of the night, though, as neither Flair nor Orton could prevent Goldberg from beating Triple H and walking away with the Raw World Championship. An upset Triple H joined Flair & Orton in defeating Maven, Jindrak & Cade on the next Raw, and Flair had a mini-feud with Maven (as well as Jindrak & Cade) over the next few weeks. On one Raw, Flair was scheduled to fight Maven, but claimed to have a hamstring injury. However, after Maven beat Rico in a match, Flair attacked him with a crutch, showing that he was fine. The two wrestled a week later, with Flair getting the tainted victory.
But Evolution's main attention was still focused fully on Goldberg. Triple H set a bounty on the new champion, saying that anyone who could beat him would get $100,000. Although several tried, it turned out that a member of Triple H's own stable collected, as Batista surprisingly returned from injury to attack Goldberg with a chair, badly injuring his leg. Although Evolution celebrated the next week, the celebration was short-lived, as co-GM Austin announced that Goldberg would face Triple H for the title at the next PPV. Da Man returned only a few weeks later, getting his revenge on Batista with a Spear, then dishing one out to Flair as well. At the '03 Survivor Series, Flair did all he could to help Triple H regain the title, including giving him brass knuckles and repeating going after Goldberg. But in the end, after Flair, Orton, & Batista had all taken sledgehammer shots, Goldberg defeated Triple H with the Spear/Jackhammer combination, keeping the gold away from Evolution.
With Batista back in the mix, Flair had another great talent to mentor to. He & Batista regularly teamed up going into December '03, and got some big wins, including a victory over Shawn Michaels & Chris Jericho (albeit because Jericho super-kicked Michaels). Flair also helped Batista get a big victory in a "Non-Title" Match with the Intercontinental Champ, Rob Van Dam. This was a purposeful match, as it weakened RVD going into Armageddon '03, where he would be facing Randy Orton. Even with the new co-GM, Mick Foley, as the special referee, Flair found a way to become involved, repeating distracting Foley. Although Foley punished Flair for this with some right hands, this allowed Orton to get in a low blow followed by the RKO, winning the IC Title. Flair tried similar tactics for Batista, but couldn't help the big man get past Shawn Michaels. However, Flair had a masterstroke of genius later on, taking the enraged Batista and getting them in as a last-minute entry to the Tag-Team Turmoil Match, where they easily defeated the exhausted Dudley Boys to become the Raw Tag-Team Champions. Finally, after more than 3 1/2 years, Flair was again wearing gold.
Evolution finished off the night by helping Triple H regain the Raw World Title in a "Three Way" Match with Goldberg and Kane. This gave every member of Evolution a major title to call their own. On the Raw following the PPV, Flair, Batista, & Triple H teamed up to face Michaels & RVD in a "Handicap" Match (after Goldberg was suspended by co-GM Bischoff). In a surprising finish, Michaels knocked out Triple H with some Sweet Chin Music to get the win, upsetting the champs. Still, Evolution couldn't consider it a bad night, as Orton won, via forfeit, over Mick Foley (who walked out), ending Foley's run as Co-GM. On the final Raw of '03, Flair got himself made the special referee in a match between the Dudley Boyz and a couple of unknowns. This was, of course, a ruse, as Flair actually disqualified the Dudleyz for using a closed fist! The Dudleyz then went to attack Flair, only to have Batista appear and take both men out.
Flair & Batista defended the Raw Tag-Team Titles against the Dudleyz to start off the new year. Thanks to Triple H distracting the challengers, the champions were able to get the victory, retaining the belts. The feud continued between Flair & Batista and the Dudley Boyz heading into the '04 Royal Rumble, where the belts were once again on the line. Thanks to Steve Austin (who had returned following Foley's departure as the Sheriff of Raw), the match was made a Tables Match, the Dudleyz' specialty. The match featured many close calls for the champions, but they managed to avoid the tables. Near the end, Flair looked to be in danger of a 3-D through a table, but the Dudleyz became distracted by the Coach, who had previously been injured by them. The Dudleyz simply took down the Coach and prepared for their Wassup Drop on him, but Flair made the save, and a recovered Batista got the Spinebuster through a table on D'von to win the match, once again keeping the titles.
Twenty-four hours later, Flair, Batista, & Orton won a "Handicap" Match over Chris Jericho & Rob Van Dam, with Orton knocking out Jericho with the RKO so that Batista could make the pin. Later on, Flair & Batista tried to help Orton in a brawl against the recently-returned Mick Foley, but with Foley fighting them all off with a steel chair. A week later, Flair had a confrontation with Chris Benoit, who had won the Royal Rumble and subsequently had jumped to Raw to contend for Triple H's Title at Wrestlemania. Flair taunted Benoit, the former Horsemen, about how he had never been able to win the big one. Later that night, Flair & Batista defended the Raw Tag Titles against Chris Jericho & Christian. At one point, Flair was tapping out to the Walls of Jericho, but the referee was distracted by the other two wrestlers. Batista then freed Flair and injured Jericho's leg, allowing Flair to get on the Figure Four for the victory.
On the next Raw, Flair had a great match with Benoit, with the two going back and forth against each other. Benoit won out with the Crippler Crossface, forcing Flair to tap out. In the middle of February '04, Flair & Batista were placed in a Tag-Team Title defense against Rob Van Dam & Booker T. Although Orton interfered on Evolution's behalf, he was chased away by Foley, leaving it a 2-on-2 contest. In the end, Flair got the Figure Four on Booker T, but RVD came off the top ropes with the Five Star Frog Splash, nailing the defenseless Nature Boy. Booker T then made the cover to win away the tag-team titles. Later in the night, Orton called out Foley, but it was an ambush, as Flair & Batista joined in on beating down the Hardcore Legend. For the next month, Flair, Batista, & Orton feuded with Foley, who brought in his own partner in the Rock.
At Wrestlemania XX, Flair, Batista, & Orton fought in a "Handicap" Match with the Rock 'n' Sock Connection. Despite the odds against them, Foley & the Rock were in control at the start of the match, keeping the heels off-balance. Thanks to Batista pulling down the ropes to send the Rock flying, Evolution took back the momentum, with Flair controlling the Rock for a time. The Rock eventually made the hot tag to Foley, but the odds again worked in Evolution's favor, as Flair was able to take Foley down as he went for the Mandible Claw on Orton. Near the end, Flair had the Rock down, and went for a version of the People's Elbow, only to have the Rock block it, then score his own People's Elbow. The Rock then got the Rock Bottom on Orton, but Flair broke up a close count. Batista later got the Batista Bomb on the Rock, basically taking him out of the match. Foley still almost got the win with the Mandible Claw, but Orton blocked it with the RKO and got the win for Evolution.
At the same event, Triple H had lost the Raw World Title to Chris Benoit in a "Triple Threat" Match also involving Shawn Michaels. It didn't take long for Evolution to regroup and want a piece of the new champion. On the next Raw, Flair, Batista, & Orton were given a "Handicap" Match against Benoit & Michaels. It started out good for Evolution, especially with Triple H becoming involved, but things started deteriorating when Orton was chased away by Foley. In the end, Michaels took out Triple H with some Sweet Chin Music, then wrestled with Flair, even as Batista got caught in the Crippler Crossface and was forced to tap. A week later, a "Draft Lottery" took place between Raw and Smackdown, with the shocking revelation that Triple H had been drafted for Smackdown! This would change within the week, though, as Bischoff worked some trades to get Triple H back (in exchange for Booker T & the Dudley Boyz). Meanwhile, the night wasn't a total loss for Evolution, as Flair & Batista won a rematch with Rob Van Dam & Booker T, thanks to a mis-directed kick by RVD, to become the two-time WWE Raw Tag-Team Champions.
Flair and the rest of Evolution soon joined Triple H in his mini-feud with the new Raw wrestler, Shelton Benjamin (who had been drafted from Smackdown). Benjamin surprisingly upset Triple H in a match, pinning him. This led to a rematch being signed, with no "unauthorized" wrestlers to be at ringside. However, Flair was made the ring announcer, Batista became the official timekeeper, and Orton was the trainer, allowing all to be involved. Despite this, Benjamin was able to win again, this time by sling-shotting Triple H into the turnbuckle post outside the ring, then getting back in, winning via countout. Evolution attacked Benjamin after the match, bloodying him, with Benoit, Foley, & Michaels making the save. This led to Bischoff calling out the four faces later that night, making an announcement that they would face Evolution the next week. Evolution then came out of the crowd and attacked the four men, beating them down.
On the next Raw, Flair disputed that Benjamin had ever beaten Triple H, saying that he just wasn't good enough. Flair wanted a match with Benjamin at the next PPV to prove it. Benjamin provided his answer to the challenge by choking out Flair, with Bischoff having to call for security to make the save. Later that night, the faces defeated Evolution, with Michaels getting some Sweet Chin Music on Orton for the win. At Backlash '04, Flair tried to use his experience to his advantage against the young gun, Benjamin, who controlled the early tempo of the match. Flair eventually came back, nearly getting Benjamin with the Figure Four, but Benjamin was able to roll over and reverse the hold. An irate Flair got free and went for a chair, but was stopped by the ref, allowing Benjamin to take control again. Flair made one last comeback, but again made a mistake by attempting to cheat, grabbing for some brass knuckles. Before he could get out of the corner to use them, Benjamin got a Stinger Splash, then came off the top rope with a flying clothesline to get the win over the Nature Boy.
On the following Raw, after Evolution had beat down both the Raw World Champion, Chris Benoit, & Edge, Bischoff made a match between Flair & Batista and Benoit & Edge for the Raw Tag-Team Titles. Despite plenty of interference from Triple H, a spear from Edge on Batista led to the pinfall, costing Flair & Batista the tag straps. The duo got a rematch for the belts the next week, with similar results, as this time Flair tasted the Spear and lost the match. In May '04, after taking a week off, Flair returned to action, helping both Batista and Orton win their respective matches over Tajiri and Edge. Flair later had to face Edge because of his actions, and almost won thanks to interference from Orton. But when Shelton Benjamin took care of Orton, Edge got the Spear and the victory.
Going into June '04, Flair continued to mainly stay outside the ring, while trying to aid his fellow Evolution members. At Bad Blood '04, Flair helped Orton stay the Intercontinental Champion, beating Shelton Benjamin, although Benjamin did have Flair in the Figure Four at one point during the match. On the next Raw, it was announced that Triple H would be facing GM Eric Bischoff's nephew, Eugene, in a #1 Contenders Match in a week. This led to Evolution pretending to befriend Eugene, who said that Triple H was his favorite wrestler. On the same Raw, Flair, Orton, & Batista took on Chris Benoit, Chris Jericho, & Edge in an "Elimination" Match. After Jericho eliminated Batista, he had Flair in trouble as well, trapping the Nature Boy in the Walls of Jericho. But, with the referee distracted, Orton came in and got the RKO on Jericho, allowing Flair to get the pin. Another RKO eliminated Edge, but Flair & Orton combined couldn't stop the World Champion, Benoit, who first made Flair tap to the Crippler Crossface, then eliminated Orton with the Sharpshooter.
Flair and the rest of Evolution continued to "pal" around with Eugene, even after Triple H brutally beat down the 'special' talent in the Contenders Match. Triple H explained the beating by pointing out Chris Benoit's 'interference' (Benoit accidentally hit Eugene with a chair). Eugene was then named an honorary member of Evolution, despite Flair and the other members of Evolution objecting. Flair's objections got worse when, as GM for the day when Bischoff was gone, Eugene made a match at the next PPV, teaming himself & Flair against the Raw Tag Champs, La Resistance! Later that night, Flair, Triple H, & Eugene teamed in a "Handicap" Match against Benoit & Edge. Although Eugene and Benoit had been friends, Evolution's influence proved too strong in the end, as Eugene nailed Benoit with a chair when the champ had Triple H in the Sharpshooter. Flair then took a crying Eugene to the back, even as Triple H won the match with a Pedigree.
At Vengeance '04, Eugene showed up along with Flair & Evolution, still being an honorary member. Early in the night, Eugene was met by Benoit, who tried once again to explain about Evolution. But Helmsley was able to make Eugene forget Benoit's warnings by giving Eugene a Ric Flair robe to wear for the tag-team title match. Not surprisingly, Flair was very upset by this 'donation', but Triple H was able to talk him down. During the match, Eugene acted just like Flair, down to the "Wooos" and the moves, including taking a few steps forward and dropping on his face. Flair seemed to not appreciate the parody, and got into the ring to show Eugene how it's actually done. La Resistance later used some dirty tactics to take the advantage, then angered Eugene by dropping him off the apron. After they got Flair with the Au Revoir, Eugene rushed the ring, angrily attacking both members of the tag-team champions, as well as shoving the referee, leading to the disqualification and keeping the Tag-Team Titles from Flair.
Later in the night, Eugene's mistakes also cost Triple H his chance to regain the World Title from Benoit. On the next Raw, a contrite Eugene came into the Evolution locker room. Flair looked ready to join Orton & Batista in beating him down, but Triple H stopped it, saying that he wasn't mad at Eugene, but that Bischoff wanted to see him. Bischoff later said he was proud of Eugene, and gave him a World Title match against Benoit. But this was a set-up, as Evolution beat down both men. This later backfired on Evolution, though, as Eugene became involved a few weeks later during Triple H's Iron Man Match against Benoit, with Eugene laying out all of Evolution, as well as Bischoff, with chair shots to help Benoit win. This led to Triple H destroying Eugene's mentor, William Regal, the next week, and getting a match against Eugene at the PPV.
Meanwhile, Flair was splitting his concentration between Triple H and Randy Orton, who had won the #1 Contenders Battle Royal to earn a shot against Chris Benoit. Flair teamed with Orton & Batista on the first Raw of August '04 to take on Benoit, Chris Jericho, & Edge. Bickering between Jericho & Edge (who were to face for Edge's Intercontinental Title, along with Batista) helped Evolution out, and in the end, Orton caught Benoit, who had Flair in the Sharpshooter, with the RKO and pinned him for the win. Also around this time, Flair had come out with his autobiography, which sold well but also caused some controversy due to Flair's comments about Bret Hart and Mick Foley, among others (Flair & Foley supposedly later got in a backstage scuffle over this, but this is unconfirmed).
At Summerslam '04, Flair came to ringside along with Triple H in his match against Eugene. Near the end of the match, Eugene had remarkably used a Pedigree on Triple H, and seemed to have the match won, only to have Flair put Triple H's foot on the ropes. The ref saw him do it, though, and ejected Flair from ringside. It wasn't over for Flair, as he was nailed by William Regal's brass knuckles on his way up the aisle. But while this was happening, Eugene was caught by a recovered Triple H, Pedigree'd, and pinned, getting Evolution a much-needed victory. Later that night, Orton was able to dethrone Benoit for the World Title without help from Evolution. This led to a rematch being signed on the next Raw, with Triple H promising to be there for Orton. Flair and the gang did come down when Orton was in the Crippler Crossface, and while Benoit was able to fight them all off, Orton got the RKO and won out. After the match, Batista hoisted Orton onto his shoulders, with Flair and Triple H seemingly celebrating the victory. However, Triple H then went from thumbs up to thumbs down, and Batista threw Orton to the ground, leading to Evolution beating down the new champion!
Twenty-four hours later on Raw, Evolution came out to talk about why they had kicked Orton out of the group, basically stating that Orton should have softened Benoit up for Triple H, not taken the title. Flair told Orton to do the right thing and hand over the title. Orton then came down and made as if to give the belt to Triple H, but instead spit in his face, then clocked him with the belt. Orton then ran out before Flair & Batista could grab him. Later in the night, Flair wrestled William Regal, with Batista and Eugene in their respective corners. Flair nearly won with the Figure Four, but tried to cheat, using Batista to hold his arms for pressure. The ref caught them, though, and started arguing with Batista, allowing Eugene to enter and reverse the hold. Later on, Flair grabbed some brass knuckles, but Regal had his own pair and was quicker, knocking Flair out and winning the match.
The next week, Flair cost Regal his match with Batista by using his pair of brass knuckles. That same night, Flair tried to bring the brass knuckles again in his match with Chris Benoit, but the ref found them in his knee pad. Flair thus had to have a fair match with the former champion, and was in danger of losing to the Sharpshooter when Batista came down and caused the DQ, Batista-Bombing Benoit. This made it a good night for Evolution, except at the end, when Orton caused Triple H to lose to Eugene in a No DQ Match. The feud between the four men continued the next week, as Flair & Batista teamed with La Resistance to take on Benoit, Regal, Rhyno, & Tajiri. Despite Evolution's best efforts, Rob Conway tapped out to Benoit's Sharpshooter for the loss. Evolution also couldn't contain Orton, who won a Steel Cage Match over Kane, then managed to escape despite being chased by four wrestlers.
At Unforgiven '04, Flair & Batista went against Benoit & Regal. The match started off fast, with Benoit almost immediately going for the Crippler Crossface on Batista, who was able to escape to the outside. After a few more go-betweens, each man tagged in their partner, with Flair and Regal going at it. Flair was on the receiving end of a lot of punishment from both Regal & Benoit for a while, until he was able to tag Batista. The tags continued to go back and forth, with Benoit & Regal in control more often. Near the end, Flair got nailed by Benoit's Flying Headbutt, then was placed in the Crossface, only to have Batista make the save by picking Benoit off the ground and slamming him. As Batista went to deal with Regal, Flair went for the Figure Four, only to have Benoit reverse it into the Crossface, forcing Flair to tap out.
Evolution came back later in the night, and despite Flair taking an RKO, they were able to help Triple H win back the Raw World Title. On the next Raw, Flair & Batista joined the new champ in an in-ring celebration, complete with a giant cake. It turned out, though, that neither Flair nor Batista had ordered the cake, which had a surprise inside. Orton came flying out and attacked, throwing Flair & Batista from the ring and knocking Triple H down with the title. Because of this, GM Bischoff gave Evolution a 3-on-1 Handicap Match against Orton that night. Technically, Evolution lost the match via DQ, as, when Orton seemed to have the edge, all 3 attacked him at once. As Flair and the rest were beating down Orton, though, Shelton Benjamin & Chris Benoit ran out to make the save, ending with Batista tasting 3 finishing maneuvers in a row.
On the next Raw, Vince McMahon came out and announced that a new type of PPV would occur in October, called Taboo Tuesday. The event would have the fans voting on match-ups that would occur at the PPV. One of the matches that was arranged was between Flair and Orton, with Flair promising to teach the young rebel what the Nature Boy was all about. At the show, it was announced that the fans had voted for the two men to fight it out in a Steel Cage Match. Both wrestlers were quickly busted open, due to being tossed into the cold, unforgiving steel. Flairtried repeatedly to escape the cage, while Orton seemed more intent on doing damage to his former ally. In the end, Flair nailed Orton with a shot from some brass knuckles, but still couldn't pin him. So Flair headed to the door, only to be stopped by Orton. The Nature Boy was, however, able to grab a steel chair from outside, but he missed his swing, and Orton got the RKO to get the pinfall victory.
On the next Raw, with Bischoff away because of his getting his head shaved at Taboo Tuesday, Evolution declared themselves in control of the show. Flair demanded a rematch with Orton, which Triple H quickly granted. Orton then came out to try to get Triple H for the title instead, with Triple H saying that, if Orton could again beat Flair, he'd get a title shot, but if Flair won, Orton would never get another chance at Triple H's belt. Throughout the night, Evolution had confrontations with the faces of Raw, namely Chris Benoit, Chris Jericho, and Maven. At the end of the night, during Flair's match with Orton, Flair tasted the RKO again. Batista started to come out for the save, but was stopped by the 3 faces. However, Triple H came from the other side and knocked Orton out with a chair shot, allowing Flair to get the pinfall victory, keeping Orton from the title. The win didn't help Flair or Triple H, though, as the rest of the faces from Raw came out and joined together in a complete beatdown of both men, with Flair once again getting knocked out by the RKO.
An upset Flair & Batista took out Tajiri on the next Raw, then came to the ring, angrily demanding retribution (while Triple H wasn't there). Instead, GM Bischoff came out, apparently angry himself at the fact that Evolution didn't save him from getting his head shaved. He made a "Survivor Series Elimination" Match for the next PPV, with the winners getting to control Raw for a month. Surprisingly, Flair was left off the heel team, which consisted of Triple H, Batista, Gene Snitsky, & Edge. When Flair protested, Bischoff just put him & Batista in a "Handicap" Match against Jericho, Maven, & Orton (3 of the 4 face team, with Chris Benoit being the other). Although a Triple H appearance was teased (it was Tajiri dressed up like him), there was no help for Evolution, who lost the "Handicap" Match.
Flair did make an appearance at the '04 Survivor Series, coming down with Triple H's team for the Elimination Match. But Flair was ejected by the ref after hitting Chris Jericho, and had to watch from the back as the face team won, meaning that they would be in control of Raw for the next month. On the next Raw, Maven was the GM-of-the-Week, and he quickly booked a World Title Match between himself and Triple H. Despite Flair and Triple H trying to convince Maven to instead join Evolution, Maven sticks with the title shot. Soon after the match begins, Batista, then Flair, were ejected, but an attack from Snitsky helped Triple H retain the title. A week later, Benoit was in charge, and made a "Steel Cage" Match with Triple H. Meanwhile, though, there seemed to be dissention between Triple H and Batista, with Flair trying to be the middle man. Flair failed, as Batista took out Triple H in the back, keeping Triple H from facing Benoit in the World Title Match. Benoit defeated Edge instead. Later on, Batista and Triple H faced off in the ring, with it turning out to be a swerve. All 3 members of Evolution celebrated the dodge, until Randy Orton came out and said that next week, there would be a battle royal with the title up for grabs!
A week later, Vince McMahon made a slight change, saying that Triple H would face the winner of the Battle Royal, since he didn't want to chance someone like Stephen Richards lucking out and winning the big belt. Flair competed in the Battle Royal, but was shockingly eliminated by Batista! Benoit & Edge both went out at the same time to 'win' the title shot against Triple H. In the back, Flair had a tirade against Batista, who said it was an accident. Later in the night, Flair took out his frustration in a "Legends" Match against Jerry "The King" Lawler, beating him with the Figure Four. At the end of Raw, Flair & Batista were once again thrown out during the match, which led to Edge & Benoit both seemingly winning and vacating Triple H's Raw World Title.
Dissention really started to grow between Batista and Triple H going into December, as Triple H blamed him for not being there to save the title. Flair seemed to be the go-between, but sided more with Triple H. During the night, when Triple H found out that a returning Eric Bischoff would decide the title's fate, he called up the GM and started to threaten him, but Batista hung up the phone, saying that Triple H was making a mistake, causing more stryfe. Later on that night, Batista & Triple H were put in a tag-team match against Benoit & Jericho, with Flair at ringside. Evolution did well in the match, but lost it via DQ when Helmsley decided to use a chair on Benoit. He then swung at Jericho, but hit Batista instead, knocking him down. Helmsley then laid out Jericho and tried to apologize to the hurting Batista.
A week later, Bischoff announced that there would be a 6-man Elimination Chamber match at the next PPV, with the Raw Championship on the line. The competitors would be Triple H, Benoit, Jericho, Randy Orton, Edge, and, in a big twist, Batista! Flair had his hands full trying to keep the two men from breaking up Evolution as 2004 headed to a close, especially when Batista defeated Rhyno quickly enough on the last Raw of the year to win the coveted last entry into the Elimination Chamber. Triple H yelled at Batista after the show, with Flair stepping back, as Batista growled that Triple H was starting to piss him off. It took Flair separating the two to bring things back to order.
On the next Raw, Flair came out with Tiple H, who had a match with Randy Orton. Triple H had asked Batista not to come out, so he could handle business 'by himself', not counting Flair. Late in the match, though, when Orton got rid of Flair and seemed to have Triple H in trouble, Batista came out, only to brawl with Chris Benoit, while Triple H lost. Flair had little to do with New Year's Revolution, as he was excluded from the Elimination Chamber Match. Instead, he worked on moral support, trying to make sure that Triple H and Batista would work together to get Triple H the title back. Things somewhat worked out according to plan, as, after Batista was eliminated by Randy Orton, he knocked Orton out with his clothesline. Triple H then got the Pedigree for the victory, regaining the Raw World Title.
Twenty-four hours later on Raw, Helmsley praised Batista as a team player, with Flair chipping in his own two cents. But Orton interrupted the celebration and talked Batista into seeing a video of the match, showing that Helmsley had a chance to save Batista from elimination, but didn't take it. This caused more friction between the Evolution members. Later on, when Batista took on Randy Orton, with the winner to get a World Title shot, Flair & Triple H took up ringside seats. Late in the match, while Flair distracted the referee, Triple H tried to give Batista a steel chair to use, but Batista wouldn't take it. The argument between the two allowed Orton to slam Batista forward into the chair (as well as Triple H) and got the roll-up victory.
Batista seemed to forgive Triple H the next week on Raw, but tensions were still high between the Evolution members, especially when Batista was given a chance to be in the Royal Rumble match. Flair & Triple H tried to talk Batista out of it, saying that they should be focusing on Triple H's World Title defense against Orton at the PPV. Batista said he would think about it. A week later, Flair & Triple H came out to interrupt a ceremony for Jim Ross (it was Jim Ross Day in Oklahoma). Flair & Triple H told J.R. and his guest, Danny Hodge (an old legend of Oklahoma NCAA wrestling), to leave, while telling Stacey Keibler to stay. When J.R. wouldn't leave her behind, Flair gave him a low blow from behind, then the two took out Hodge as well. Triple H then threatened to Pedigree Keibler because of the kiss she had given Orton the week before, but Orton made the save.
Flair & Triple H bragged to Batista about what they had done later on, with Batista apparently not impressed by the beatdown of an announcer, an old man, and a woman. Batista then told his fellow Evolution mates that he had decided to take the qualifying match for the Rumble. While Flair & Triple H were upset, Batista explained that he was doing it because, if Helmsley lost the title to Randy Orton, Batista could get it back. Batista went on to win a Handicap Qualifying Match, defeating the Tag-Team Champs, La Resistance, on his own. Flair later was announced by Triple H that he, too, would be in the Rumble, supposedly for more Evolution 'security'. Flair went against Orton in the main event, with Triple H & Batista at ringside. At one point, when Triple H tripped Orton from the outside, the referee blamed it on Batista, throwing him out. Later in the match, with the ref being down, Flair & Triple H double-teamed Orton, with Flair getting on the Figure Four. But despite the double-team, Orton fought back, taking Triple H to the outside, then getting Flair with the RKO for the win.
At the '05 Royal Rumble, Flair got the best draw of all, coming in at #30. He quickly teamed up with Batista, and had a successful run, with the two eliminating the Coach and Chris Benoit. Later on, though, after Batista had thrown out Christian, Flair attacked, trying to eliminate him. Batista then turned, with Flair claiming it was all a mistake. Flair was then attacked by both Rey Mysterio & Edge, who threw him over the top rope, eliminating him. After a confusing ending, where both Batista and John Cena went over the top rope together, Vince McMahon had the match restarted, with Batista getting the victory.
For the next few weeks, the main speculation on both Raw and Smackdown was, where would Batista go? Having won the Rumble, Batista had the choice of challenging either World Champion on the two shows. While Triple H seemed to be interested in a match between the two men, he also decided that Batista should take the Smackdown Title from John Bradshaw Layfield. Flair seemed torn, not wanting the strength of Batista to leave Raw, but quickly got on Triple H's side when the champ explained that Evolution would rule both shows. Flair called Triple H a genius. Around this time, Smackdown interviews mysteriously began playing on Raw, showing different Smackdown superstars bad-mouthing Batista, seemingly convincing him more to go to the show and prove himself. Meanwhile, Flair & Triple H teamed up to take on Shawn Michaels & a concussed Randy Orton. Despite the concussion, though, interference from Edge (who was given a World Title shot against Triple H to take place the next week) allowed Orton to pin the champ, causing Evolution to lose the match.
When Raw appeared live in Japan the next week, Flair had another "Legends" Match, this one against Shawn Michaels. Although Flair had his moments, Michaels was just too strong, knocking him out with some Sweet Chin Music for the victory. A week later, Flair was shown in the dressing room, dressed in a nice suit, when Triple H came in with his wrestling gear on, announcing that they had to be ready, since a rumor said that the Smackdown champ, JBL, was coming to Raw! Flair & Triple H seemed to want to gang-attack JBL if he showed up, while Batista proclaimed that he wanted to do it alone. At the end of the night, JBL's limo was spotted outside, and Batista quickly went to confront the man. But the limo was ready for him, and almost ran him down, with Triple H shoving him out of the way. Flair, after the limo had passed, ran over to check on both men. Evolution glared & yelled at JBL as the limo drove away.
Batista appeared on the following Smackdown, where JBL proclaimed his innocence, saying that someone had stolen his limo for the night (Batista didn't seem to care, destroying the limo). Batista also appeared on the Smackdown PPV, which made it seem like a sure thing that he was leaving Raw. However, on the night of the contract signing, Triple H told Flair that he was actually the one behind the Smackdown interview clips and the limo assault, saying that he was doing it for Batista's own good, when it was obvious it was because he didn't want to face Batista. Once again, Flair called him a wrestling genius, praising the champion. All the while, Batista was listening just outside the door. Later on that night, Batista, along with Flair & Triple H, made his way out to where Bischoff & Theodore Long were waiting. After speeches from both GMs, as well as Triple H, Batista announced that he had known all along what he wanted. He dropped the Raw contract and seemed to be about to sign with Smackdown, giving the thumbs up to Evolution. But as Flair & Triple H celebrated, Batista changed it to a thumbs down, then attacked, throwing Flair out of the ring, then Batista Bombing Helmsley through a table! Batista then signed the Raw contract, saying that he was coming for Triple H's title!
A week later, Flair & Triple H seemed interested in nothing but revenge. Triple H said in the ring that he would beat Batista within an inch of his life as soon as the Animal arrived. However, when he did show, and Flair told Triple H that they needed to go get him, Triple H said he had another plan. When Batista came out for an interview later on, Triple H & Flair headed out as well, surrounding the ring. However, when both went to get into the squared circle, only Flair made it, as Triple H stepped back out. Batista then destroyed the Nature Boy, eventually Batista Bombing him and leaving him laying. An outraged Triple H opted not to come in, and instead left Flair laying in the ring. The champ headed to the back and yelled at GM Bischoff, eventually demanding a match the next week between Batista... and Flair.
Flair seemed distinctly unsure of the match on the next Raw, as he'd already felt Batista's power. But Triple H convinced him that, with Triple H and his 'friend' the sledgehammer with them, Flair couldn't lose. However, as the two (or three, if you will) headed to the ring, Bischoff stopped them, saying that he couldn't let Triple H destroy his Wrestlemania main event, and wouldn't let the sledgehammer come with them, much to the terror of Flair. The Nature Boy still did the best he could against the Animal, even getting the Figure Four at one point, with extra pressure added from outside from Triple H. But even with the Raw World Champ trying to help, it was no good, as Batista got rid of Triple H, then Batista Bombed Flair again, this time for a pinfall victory.
A week later, Flair was seen many times during the night 'motivating' Gene Snitsky, who was in a match with Batista. Flair kept telling Snitsky that, if he injured Batista, it wouldn't be his fault. Snitsky disagreed, saying it WOULD be his fault, with a smirk on his face. Flair later confronted Batista in the back with Snitsky, yelling and screaming at him. Batista took it calmly, though, and told Flair that the World Title would be his. In the main event, Flair & Triple H came out with Snitsky to 'support' him. They also interfered early on, trying to help the big man slaughter Batista. But Batista again was too strong, and was about to Batista Bomb Snitsky when Flair entered the ring, chop-blocking his knee. Triple H joined in, as the match went to a disqualification. Afterwards, Batista fought off the 3 heels, but was quickly surrounded again, this time with all 3 armed with chairs. Kane made the save, though, beating down Snitsky even as Batista got rid of Flair & Triple H. After the match, Triple H (who had the power to pick Batista's opponent for the next week) chose Kane.
It was announced on the next Raw that not only would Batista have to fight the Big Red Machine, Kane, but it would also be a "Lumberjack" Match, with wrestlers handpicked by Triple H at ringside. The plan somewhat backfired on Triple H, though, as some of the wrestlers also had a grudge with Kane, and attacked him as well during the match. In the end, both Batista and Kane took out most of the lumberjacks, then got back to the fight, with Kane nearly winning with a Chokeslam. But Batista came back and got the Batista Bomb to walk out victorious, with Triple H & Flair angrily looking on from the announcers' table. Triple H & Batista had an orchestrated Face-Off on the final Raw before the big event, with security at hand if needed. Flair nodded as Triple H talked about how he had created Batista, and subsequently been betrayed. Batista simply said he would take the title, that Flair was a true legend, and that Triple H was an a**hole. This led to Triple H throwing over the table between them and slapping Batista, prompting a "thank-you" from the Animal, since this allowed him to fight back. The two brawled, with Flair, Bischoff, & security all trying to break them up.
At Wrestlemania 21, Flair came down with Triple H, there to help him against the threat of Batista. Flair distracted Batista at one point, and later choked Batista from the outside, doing all he could to help his man win. Later on, when the ref was knocked down, Flair entered with the belt, looking to knock Batista out, only to taste the Spinebuster. This basically took Flair out of the match, as Batista would later Batista Bomb Triple H and win away the WWE Raw World Heavyweight Title, leaving Flair & Triple H to stew over the defeat from a former ally. Over the next few weeks, Flair & Triple H planned on how to get the gold back, with Triple H even wrestling announcer Jim Ross at one point. Thanks to Batista coming down and taking out both Flair & Triple H, JR got the win, embarrassing both men.
When it was announced that Christian would be facing Batista in a "Non-Title" Match, Flair went to talk to Christian about a plan for that night. Christian shrugged him off at first, but when Kane took out Christian's bodyguard, Tyson Tomko, Christian came back and nervously talked with Flair & Triple H. It was soon set up that the Coach would be the referee, Flair would be the timekeeper, and Triple H would be Christian's "manager". This put the odds severely against Batista, since the Coach didn't call any interference from Flair or Triple H. However, Batista still took out everyone, Batista Bombing Christian and pinning him (while using a limp Coach's arm to make the count. After the match, though, Triple H Pedigree'd Batista, leaving him laid out.
Flair again accompanied Triple H to his rematch against Batista at Backlash '05. Flair continued to be a major asset for Triple H, at one point distracting the ref while Triple H used the title, hitting Batista and getting a near fall. When the ref got knocked down later in the match, Flair entered, but got taken out by Batista. With Flair down, Triple H again got caught, getting the Batista Bomb and getting pinned. Once again, Flair & Triple H and failed to regain the gold. A Gold Rush Tournament was set up on the following Raw, with Triple H facing Chris Benoit in the first round. Flair worked hard to help Triple H screw over Benoit, but when the ref was out (again), Batista ran down, taking out Flair, then helping Benoit get up and get the Sharpshooter on Triple H. With Batista grinning from the outside, holding back the rope, Triple H was forced to tap out, losing another shot. Due to this defeat, Triple H "took his ball and went home," leaving Flair behind. Flair begged for Triple H to stay, but he instead drove off, with Flair blaming Batista for making him go.
In the coming weeks, Flair had more problems with Christian, due to Christian mocking Triple H's defeat in the tournament. Flair wrestled Tyson Tomko on the next Raw, defeating him to earn a shot against Christian. On the next Raw, Flair talked with Batista, who seemed to be supporting Flair now that Triple H was gone. That night, Flair managed to defeat Christian with some dirty tactics, using the ropes to get the win. An embarrassed Christian attacked Flair after the match along with Tomko, until Batista surprisingly came down to make the save. A week later, Batista was set to defend the World Championship against Edge, with Christian & Tomko working with Edge to help him win. Late in the match, though, Flair came out to return the favor, battling against all three men. Although Flair got Speared by Edge, he helped Batista regain the momentum, with the champ landing the Batista Bomb on Edge for the victory. After the match, Flair and Batista looked to be coming back together as a team. However, Triple H's music then hit, and as Batista was distracted, Flair gave him a low blow, showing that he was still united with the Game! Triple H then came down and beat Batista down, before announcing that he'd be facing Batista in a "Hell In A Cell" Match at the next PPV!
Flair worked with Triple H over the next few weeks in their preparations for the next title shot, standing with Triple H during the contract signing for the Hell In A Cell Match. At the time, a Draft Lottery was taking place between Raw and Smackdown, leading to some interesting confrontations. On one night, Kurt Angle came out, going face-to-face with Triple H about who the #1 guy on Raw now was. When Angle gave a "Woooo" at one point, Flair told him that he was the only one who did that, leading, strangely, to a "Woooo"-off between the two men. Later on, when Angle fought Batista in a "Non-Title" Match, Flair & Triple H quickly intervened, causing the DQ. All three men attacked Batista afterwards, with Shawn Michaels coming down for the save. A tag match soon started between Triple H & Angle and Batista & Michaels, with Flair helping his team from the outside by distracting Batista. When Batista turned back around, Triple H Pedigree'd him, pinning the champion.
At Vengeance '05, Triple H and Batista went at it inside the Hell In A Cell, which basically kept Flair from getting too involved. Flair could only watch as Triple H was given a Spinebuster on the steel steps, followed by a Batista Bomb, getting pinned once again. For the third time in a row, Flair & Triple H had failed. They would not get any more opportunities against Batista, as he was drafted to Smackdown the next week. On the next Raw, Kurt Angle came out wanting another shot at Batista. Flair interrupted him, though, talking about how Triple H deserved another shot. Flair and Angle again had a "Wooo"-off, leading to the two signing to face in a match that night. It was a great bout, with Flair showing that he still had it in the ring, nearly getting the win with the Figure Four. But Angle came back and got his Ankle Lock, forcing Flair to tap out. Flair & Triple H then both disappeared from television for a few months, to rest and be with their families.
In late August '05, Flair returned to Raw, appearing as a guest on Carlito's Cabana. Carlito at first called Flair the greatest guest ever on his show, but then started insulting Flair. He said that his dad (Carly Colon Sr) had said Flair wasn't that great, and now he agreed with him. Carlito then spit an apple in Flair's face, causing the Nature Boy to attack Carlito, knocking him from the ring! A week later, Flair helped save Shawn Michaels from a double-team of Carlito & Chris Masters, leading to a tag match being signed for that night. However, before the match, Flair was savagely attacked in the back, leaving him out of the match. Michaels took on Carlito & Masters in a "Handicap" Match, with a battered Flair coming out near the end to be there for him. It backfired on Flair, though, as he was caught by Masters in the Masterlock and passed out, losing the match.
Flair kept going after Carlito & Masters for the next few weeks, with Michaels backing him up. At Unforgiven '05, Flair took on Carlito for the Intercontinental Heavyweight Title. It was a match pitting experience against youth, but Flair's dirty tricks and skills helped him win out in the end, forcing Carlito to tap out to the Figure Four Leglock! Flair, shockingly, was now the Intercontinental Heavyweight Champion! After the match, Flair partied all night in his limo with several women, even taking Viagra before hand. At the end of the night, Flair was seen exiting the limo, then taking a Flair Flop on the concrete, exhausted but happy! Twenty-four hours later, Flair had a rematch with Carlito, and again came out on top, forcing Carlito to tap out. After the match, though, as Flair was being interviewed by Maria, he was double-teamed by Carlito & Masters, and left in a bloody heap.
To combat the duo, Flair announced on the next Raw that his best friend, Triple H, was making his return the next week! Flair & Triple H teamed up against Carlito & Masters at WWE Homecoming, which signified WWE's move back to the USA Network. There were little problems between Flair & Triple H, as they worked together to defeat Carlito & Masters, with Triple H Pedigree'ing Carlito for the win. After the match, Flair gave Triple H his sledgehammer, and the two celebrated... until Triple H hit Flair in the head with the weapon! Triple H beat Flair down, eventually dragging him through the backstage area and throwing the bloody Nature Boy into a limo, ordering the driver to take off. Triple H explained himself the next week, saying that Flair had gone soft, and that Triple H didn't want to see his hero end up like that. Instead, Triple H claimed he'd taken the horse behind the barn and shot him.
A furious Flair came back after a week off and called out Triple H, giving an amazing interview where his head wound started bleeding again, gushing out blood. When Triple H came out to respond, Flair immediately chased him to the back with a baseball bat. Flair continued to chase after Triple H, as it was announced that the two men would fight on the next PPV, with the fans deciding on what type of match. Flair begged the fans to make it a "Steel Cage" Match, and they listened, putting the two inside the cage at Taboo Tuesday '05. It was a brutal fight, with both men showing the anger that was between them. In the end, a bloody Flair managed to crawl out of the ring, winning the match over his former best friend. On the next Raw, Flair took on Rob Conway, with the IC Title on the line. Triple H watched from the ramp as Flair went at it, distracting him. But Flair still got the win over Conway, retaining the IC Title. Triple H attacked Flair after the match, though, showing that the two still had some major problems.
The feud was put on hold, though, the next week, as both Raw and Smackdown did a tribute for Eddie Guerrero, who had passed away that weekend. Flair wrestled William Regal on Raw, having an old-school match, with both looking to 'cheat to win', as Guerrero was known for. Flair won out, forcing Regal to submit. A week later, things went back to normal, as Flair pinned Trevor Murdoch while holding his tights, winning the old-fashioned way. Afterwards, though, Flair had to listen to Triple H cut a promo on the big screen, talking about what he was going to do to Flair. At the '05 Survivor Series, Flair and Triple H again went at it, in a "Last Man Standing" Match. It quickly got ugly, as Triple H used a screwdriver to cut Flair open! Flair came back later to backdrop Triple H through an announce table, showing that he could give as good as he got. In the end, though, Triple H landed three Pedigrees in a row, with Flair struggling to his feet each time. A frustrated Triple H then smacked Flair with the sledgehammer, finally knocking him out completely to win the match. Flair was stretchered out afterwards, with Triple H making the "gun" symbol above him, apparently finishing him off.
Only a short time later, Flair was in trouble in the real world, as he was charged with assault after an alleged road rage incident from the week before. Flair proclaimed his innocence in the matter, but the incident brought out other details, as it was found out that Flair's wife, Beth, had filed for divorce earlier in the year, accusing Flair of violence towards her. Flair was scheduled to talk on Edge's show, the Cutting Edge, but Flair backed out due to 'legal advice', leading to Edge & Lita insulting him in the ring. A week later, Flair competed in an "Elimination Chamber Qualifying" Match against Kurt Angle, but Angle used his gold medals to knock Flair out, scoring the win. Edge & Lita again made fun of Flair after the match, saying that he could only win on the roadways. Flair did go to the Christmas in Afghanistan Raw, where he defended the Intercontinental Title by defeating the Coach in a short match. On the final Raw of the year, Edge said that he finally had Flair to interview him. However, it was all a joke, as a picture of Flair was displayed on the Tron, with someone else controlling the lips, making fun of him. This was finally enough for the real Flair, who charged out and attacked Edge, with Lita coming in just long enough to help Edge escape.
On the first Raw of the new year, Edge had another video for Flair, dressing up as the Nature Boy and doing a "live video" of the road rage incident. Flair again came out to put a stop to Edge's fun, attacking Edge and going for the Figure Four. When Lita interfered again (and Edge escaped), Flair opted to put the Figure Four on Lita as well, torturing her until Edge reluctantly came back to pull her out. At New Year's Revolution '06, Flair put his IC Title on the line against Edge. Once again, Lita became involved, and once again, Flair put her in the Figure Four. But Edge then attacked with his briefcase, bloodying Flair while causing the DQ. It all turned out to be part of a master plan from Edge, as he cashed in his "Money In The Bank" contract later that night to win the WWE Raw Championship from John Cena.
Edge & Lita planned to celebrate their victory with a "Live Sex" demonstration on the next Raw. As they were going at it, though, Flair came down, attacking his foe. Unfortunately for Flair, Edge got the upper hand, taking out Flair with a One-Man Conchairto! Cena later came down for the save. A week later, Flair got a shot at the WWE Championship, taking on Edge in his specialty match, Tables, Ladders, & Chairs! Flair looked to be a major underdog, as he had never competed in a "TLC" Match before. But Flair gave it all, getting the fans to think that he might just become the Heavyweight Champion again. Both men took some horrible shots, including Edge leaping onto Flair, breaking through the announce table! Near the end, a bloody Flair was able to tip Edge's ladder over, sending Edge out of the ring and through a table! However, as Flair reached out for the title, that close to winning, Lita became involved, holding him back. Flair knocked Lita down and gave her the Figure Four, then tried to climb again, but Edge came back, punching Flair off the ladder, then getting the gold, retaining the title. After the match, Edge kept attacking Flair, again going for the One-Man Conchairto, but Cena again made the save.
A week later, Cena and Edge were set to face off in a tag match, with both needing to find partners. Edge got himself Chris Masters, but Cena's partner was a surprise, as Flair, despite the beating he had taken the week before, came out to the hometown crowd! Flair was instrumental in the match, saving Cena near the end from the Masterlock with a knee clip to Masters. This allowed Cena to take out Masters and make him tap out to the STFU, getting the win for their team. Flair next appeared at the '06 Royal Rumble, entering the Rumble at #5. Unfortunately for Flair, his run in the match didn't last long, as his old foe, Triple H, tossed him out. A day later, on Raw, Flair had a confrontation with Shelton Benjamin, who had turned around his career thanks to his Mama coming to the ring with him. Benjamin let Flair know that, now that he had his confidence back, he was coming back for the IC Title. Flair quickly told Benjamin that a Mama's Boy shouldn't mess with the Nature Boy, then walked off.
Going into February '06, Flair entered into the #1 Contenders Tournament for the WWE Title. His first foe, though, was Triple H, who managed to catch Flair with the Pedigree, keeping Flair from another title shot. A week later, Flair watched as Benjamin won a "#1 Contenders" Match over Eugene, earning the right to wrestle Flair for the IC Title. The match took place on the next Raw, with Flair working to keep the former champion down. However, when Mama Benjamin seemed to be having health issues, the ref was distracted, allowing Shelton Benjamin to use an air tank to hit Flair repeatedly with. Shelton then gave Flair the T-Bone Suplex and won the match, taking away the IC Title. Afterwards, Mama Benjamin did a little dance, showing that she was perfectly fine. It was announced a week later by Carlito that another "Money In The Bank" Match would be held at Wrestlemania, with the competitors being chosen in Qualifying Matches. Flair surprisingly managed to defeat the man who started the matches, Carlito, by rolling him up and grabbing the ropes, earning a spot in the match while a shocked Carlito looked on. The other two Raw spots were earned by Rob Van Dam and Benjamin.
Flair got a rematch against Benjamin for the IC Title a week later, with Flair looking to get some revenge on the man who took his title. During the match, Flair had Benjamin down in the corner, with the ref pushing him away. The ref then went to check on Benjamin, but took a thumb to the eye from Benjamin, who thought it was Flair! The Nature Boy caught Benjamin afterwards and locked him in the Figure Four, causing Benjamin to tap, even as the referee called for the bell. But before Flair could celebrate regaining the IC Title, it was announced that Flair had won via DQ! Flair argued with the referee, who stayed with his ruling, which meant that Flair got the win, but not the title. Afterwards, a frustrated Flair attacked Benjamin, even going to the outside to grab Mama Benjamin's oxygen tank, hitting Benjamin in the ribs with it.
On the next Raw, Flair watched from the announce table as Rob Van Dam took on Benjamin for the IC Title, in a fast-paced match. However, when Benjamin went for the belt, probably to hit RVD with it (and escape with the DQ to stay the champ), Flair interceded, grabbing the belt. Unfortunately, when RVD charged the two men, he only hit Flair, allowing Benjamin to roll him up for the pin, keeping the title. Flair and RVD had words after the match, with each blaming the other for what went down. Flair, Van Dam, and Benjamin had a "Three-Way" Match on the next Raw, with Benjamin's IC Title again on the line. It was a violent match, with Flair and Van Dam bumping heads during an RVD suicide dive, busting both men open. In the end, Van Dam tried for the Five Star Frog Splash on Flair, but missed, allowing Flair to lock on the Figure Four Leglock. As Flair increased the pressure, however, Benjamin snuck in and quickly pinned the trapped Flair, retaining the IC Title once again.
Flair came out on the next Raw with a ladder, talking about how winning another World Title was his destiny. He was interrupted by Benjamin, who started attacking Flair. Van Dam made the save, of sorts, giving Benjamin a Rolling Thunder on top of a ladder. RVD then talked about how he was going to win the title shot, only to have Flair give him an eyepoke, followed by a ladder shot, sending Flair out as the last man standing! At Wrestlemania 22, Flair, Van Dam, and Benjamin, representing Raw, went into the "Money In The Bank Ladder" Match to compete both against each other and the Smackdown representatives, Matt Hardy, Bobby Lashley, and Finlay. It was an wild affair, with lots of great moves, including Benjamin running across a ladder at one point to deliver a Senton to the outside. Flair fought hard in the match, but took a massive Superplex off a ladder from Hardy, sending Flair to the back with the EMTs. Flair would return, limping, later on, but couldn't fully compete in the bout. In the end, Benjamin and Hardy were fighting on the ladder, but Van Dam took both out by knocking down the ladder. This left Van Dam free to make the climb, grabbing the briefcase for the victory to earn the title shot, keeping Flair from returning to the big time.
Flair came out to talk to the Chicago crowd on the next Raw, still optimistic about getting to the top one more time. However, Flair's interview was interrupted by a newcomer, Alejandro Armando Estrada, who talked about how Flair was old and broken down. Estrada then introduced a new wrestler, Umaga (formerly Jamal), who beat down Flair and left him lying in the ring. Flair was helped out of the ring, and disappeared from Raw for the next few weeks, apparently recovering from his injuries (actually, he was having eye surgery). Flair returned to Raw on the April 24th, '06 Raw, attacking Umaga after one of his matches. Flair and Umaga met again that weekend at Backlash '06, with Flair intent on using his experience and intelligence to get him past the power of the monster. Flair also tried his old bag of tricks, from a thumb to the eyes to a low blow. But in the end, Umaga was too strong, taking Flair out with his thumb strike to the throat, followed by a pin.
Pay-Per-View/Show Summary: (100 - 81, 7 Draws, 3 DCOs, 1 DDQ, 2 NCs, 1 unknown)
- AWA/WWWF Title Unification (NWA Toronto) (March '79) = Flair was beaten by the NWA US Champion Ricky Steamboat.
- Mid-South Superdome Extravaganza (April 21, '79) = Flair took down Randy Tyler.
- NWA Mid-Atlantic "Battle of the Nature Boys" (July 8, '79) = Flair retained the NWA US Title, beating Buddy Rogers.
- Mid-Atlantic Battle of the Nature Boys (November '79) = Flair defeated Buddy Rogers.
- AJPW Sumo Hall (October '81) = Flair stayed the NWA World Champion by winning a "Three Falls" match over Jumbo Tsuruta.
- Sam Muchnick Retirement Show (January '82) = Flair retained the NWA World Title by defeating Dusty Rhodes.
- AJPW Sumo Hall (June '82) = Flair fought to a No-Contest with Jumbo Tsuruta. Flair stayed the NWA World Champion.
- GCW NWA/WWF World Title Unification (July '82) = Flair and his NWA World Title fought the WWF World Champion Bob Backlund to a Double Countout.
- WCCW Wrestling Star Wars '82 (August) = Flair retained the NWA World Title, defeating Kerry von Erich in 3 Falls.
- WCCW Christmas Star Wars '82 = Flair won over Kerry von Erich in a No DQ Steel Cage Match. Flair retained the NWA World Title. Michael Hayes was the referee.
- AJPW Sumo Hall (June '83) = Flair and Jumbo Tsuruta battled to a draw in a "Three Falls" match. Flair retained the NWA World Title.
- NWA (Toronto) Exhibition Stadium #1 (July '83) = Flair won, via DQ, over the NWA World Champion Harley Race.
- NWA Missouri Title Tournament (July '83) = Flair defeated Bob Brown, George Welles, Butch Reed, and David von Erich to win the tournament.
- NWA (Toronto) Exhibition Stadium #2 (July '83) = Flair lost, via DQ, to the NWA World Champion Harley Race.
- WWC (Puerto Rico) 10th Anniversary Show (1983) = Flair was beaten, via DQ, by WWC North American Champion Pedro Morales.
- WWC (Puerto Rico) Stadium Show (Dec '83) = Flair lost to Universal Champ Carlos Colon in a Steel Cage match.
- WCW Starrcade '83 = Flair won a "Steel Cage" Match over Harley Race to win the NWA World Title. Gene Kiniski was the special referee.
- WCCW Christmas Star Wars '83 = Flair lost, via DQ, to David von Erich. Flair retained the NWA World Title.
- AJPW Sumo Hall (December '83) = Flair defeated the Great Kabuki via DQ, retaining the NWA World Title.
- WCCW Star Wars (January '84) = Flair and Mike Von Erich fought to a Draw.
- WCCW Parade of Champions I (May '84) = Flair lost the NWA World Title to Kerry von Erich.
- Lords of the Ring (Florida) (June '84) = Flair retained the NWA World Title, but lost a "3 Falls" Match to Dusty Rhodes. Due to a DQ, the belt was not transferred.
- WCCW World Class Texas Title Tournament (June '84) = Flair defeated Kevin von Erich and Jules Strongbow, but lost in the Finals to Gino Hernandez.
- Mid-South Superdome Extravaganza (August 24, '84) = Flair, as the NWA World Heavyweight Champion, fought to a Double Disqualification with Kerry von Erich.
- WCW Starrcade '84 = Flair defended the NWA World Title by winning over Dusty Rhodes when the match was stopped due to Rhode's excessive bleeding. Joe Frazier was the special referee.
- WCCW Christmas Star Wars '84 = Flair lost, via DQ, to Kerry von Erich, but retained the NWA World Title.
- WCCW Parade of Champions II (May '85) = Flair kept the NWA World Title by fighting to a Double Count-Out with Kevin von Erich.
- PNCW Owen Productions 60th Anniversary Show (May '85) = Flair fought to a draw with Billy Jack Haynes, retaining the NWA World Title.
- WCW Great American Bash '85 = Flair defeated Nikita Koloff to retain his NWA World Title.
- NWA Mid-South Superdome Extravaganza (June '85) = Flair defeated the NWA World belt, defeating Terry Taylor.
- NWA Mid-South Superdome Extravaganza (August '85) = Flair defeating Butch Reed to stay the NWA World Champion.
- Polynesian Hot Summer Night (August '85) = Flair and Siva Afi fought to a No-Contest. Flair retained the NWA World Title.
- Battle of the Belt I (Florida) (September '85) = Flair again successfully defended the NWA World Title, winning a "3 Falls" Match over Wahoo McDaniel.
- WWC (Puerto Rico) 12th Anniversary Show (Sept '85) = Flair defended the NWA World Title against Hercules Ayala (unsure of winner).
- AWA SuperClash I ('85) = Flair defended the NWA World Title by defeating Magnum TA.
- AJPW 13th Anniversary Show (October '85) = Flair, the NWA Champ, and Rick Martel, the AWA Champ, fought to a Double Countout.
- WCW Starrcade '85 = Flair lost, via DQ, to Dusty Rhodes, but kept the NWA World Title.
- PNCW Superstar Extravaganza (January '86) = Flair won, via DQ, over Dusty Rhodes, staying the NWA World Champion.
- Battle of the Belts II (Florida) (February '86) = Flair continued his streak, defending the NWA World Title by defeating Barry Windham.
- NWA Mid-South Superdome Extravaganza (June '86) = Flair retained the NWA World Title, defeating Ricky Morton.
- WCW Great American Bash '86 (July 5th) = Flair stayed the NWA World Champion by pinning Ricky Morton in a Steel Cage Match.
- WCW Great American Bash '86 (July 26th) = Flair lost the NWA World Title to Dusty Rhodes in a Steel Cage Match.
- Battle of the Belts III (Florida) (September '86) = Flair fought to a draw with Lex Luger in a "3 Falls" Match, keeping the NWA World Title.
- WCW Starrcade '86 = Flair won via DQ over Nikita Koloff, retaining the NWA World Title.
- AJPW Budokan Hall (March '87) = Flair kept the NWA World Title, defeating Hiroji Wajima.
- Eddie Graham Memorial Show (May '87) = Flair lost, via DQ, to Dusty Rhodes. Flair retained the NWA World Title.
- WCW Great American Bash '87 = Flair, Arn Anderson, Lex Luger, Tully Blanchard, and J.J. Dillon lost to Hawk, Animal, Dusty Rhodes, Nikita Koloff, and Paul Ellering.
- WCW Starrcade '87 = Flair regained the NWA World Title by defeating Ron Garvin in a "Steel Cage" Match.
- WCW Bunkhouse Stampede (January '88) = Flair lost, via DQ, to Hawk of the Road Warriors. Flair retained the NWA World Title.
- WCW Clash of the Champions I (March '88) = Flair fought Sting to a Draw, retaining the NWA World Title.
- WCW Great American Bash '88 = Flair held onto the NWA World Title by defeating Lex Luger, when Luger was bleeding too badly to continue.
- WCW Clash of the Champions IV (December '88) = Flair and Barry Windham defeated the Midnight Express.
- WCW Starrcade '88 = Flair stayed the NWA World Champ by again defeating Lex Luger.
- WCW Chi-Town Rumble (February '89) = Flair lost the NWA World Title to Ricky "The Dragon" Steamboat.
- WCW Clash of the Champions VI (April '89) = Flair lost a "3 Falls" Match to the NWA World Champion Ricky "The Dragon" Steamboat.
- WCW WrestleWar '89 = Flair defeated Ricky "The Dragon" Steamboat to become the NWA World Champ.
- WCW Great American Bash '89 = Flair stayed the NWA World Champ by pinning Terry Funk.
- WCW Clash of the Champions VIII (September '89) = Flair and Sting won, via DQ, over Dick Slater and the Great Muta.
- WCW Halloween Havoc '89 = Flair and Sting defeated The Great Muta and Terry Funk in a "Thunderdome" Match. Ole Anderson (seconded Flair's team), Gary Hart (seconded Muta's team), and Bruno Sammartino (referee) were also involved.
- WCW Clash of the Champions IX (November '89) = Flair won an "I Quit" Match over Terry Funk.
- WCW Starrcade '89 = Flair defeated the Great Muta. Later, Flair fought to a draw with Lex Luger, then lost to Sting.
- WCW Clash of the Champions X (February 6, '90) = Flair, Ole and Arn Anderson defeated the Great Muta, Buzz Sawyer and the Dragon Master in a "Steel Cage" Match.
- WCW WrestleWar '90 = Flair won, via countout, over Lex Luger. Flair stayed the NWA World Champ.
- WCW Capital Combat (May '90) = Flair lost, via DQ, to Lex Luger in a "Steel Cage" Match. Flair retained the NWA World Title.
- WCW Clash of the Champions XI (June '90) = Flair lost, via DQ, to the Junkyard Dog. Flair retained the NWA World Title.
- WCW Great American Bash '90 = Flair lost the NWA World Title when he was beaten by Sting.
- WCW Clash of the Champions XII (September '90) = Flair lost, via DQ, to the NWA United States Champion, Lex Luger.
- WCW Halloween Havoc '90 = Flair and Arn Anderson fought the NWA Tag Champs Doom to a Double-Countout.
- WCW Clash of the Champions XIII (November '90) = Flair defeated Butch Reed.
- WCW Clash of the Champions XIV (January '91) = Flair, as the WCW World Champion, fought to a draw with Scott Steiner.
- WCW WrestleWar '91 = Flair, Barry Windham, Sid Vicious and Larry Zbysko won a "WarGames" Match over Sting, Flyin' Brian Pillman and the Steiner Brothers.
- NJPW Tokyo Dome '91 (Starrcade in Egg Dome) = Flair lost the NWA World Title (but retained the WCW World Title) to the IWGP Champion Tatsumi Fujinami.
- WCW Superbrawl I ('91) = Flair both retained his WCW World Title and (unofficially) regained the NWA World Title by beating Tatsumi Fujinami.
- WCW Clash of the Champions XV (June '91) = Flair retained the WCW World Title after winning a "3 Falls" Match over Bobby Eaton.
- WWF Survivor Series '91 = Flair, Ted DiBiase, the Warlord and the Mountie fought an "Elimination" Match against "Rowdy" Roddy Piper, Davey Boy Smith, Bret Hart and Virgil. Flair was the "survivor".
- WWF Royal Rumble '92 = Flair earned the vacated WWF World Title by winning the "Royal Rumble".
- WWF Saturday Night's Main Event #30 (January '92) = Flair and the Undertaker lost, via DQ, to Hulk Hogan and Sid Justice.
- WWF Wrestlemania VIII ('92) = Flair lost the WWF World Title to "Macho Man" Randy Savage.
- WWF Survivor Series '92 = Flair and Razor Ramon lost, via DQ, to "Macho Man" Randy Savage and Mr. Perfect.
- WWF Royal Rumble '93 = Flair competed in the "Royal Rumble", which was won by Yokozuna.
- WCW Clash of the Champions XXIII (June '93) = Flair and Arn Anderson won a "3 Falls" Match over the WCW Tag Champs Brian Pillman and Steve Austin. Due to one of the falls being a DQ, the belts did not change hands.
- WCW Beach Blast '93 (July '93) = Flair defeated Barry Windham to regain the NWA World Title.
- WCW Clash of the Champions XXIV (August '93) = Flair and Sting defeated Awesome and King Kong.
- WCW Fall Brawl '93 = Flair lost the WCW International World Title to Ravishing Rick Rude.
- WCW Halloween Havoc '93 = Flair lost, via DQ, to the WCW International World Champion "Ravishing" Rick Rude.
- WCW Clash of the Champions XXV (November 10, '93) = Flair won, via DQ, over the WCW World Champ Vader.
- WCW Battlebowl (November 20, '93) = Flair and Steve Austin defeated Maxx Payne and Too Cold Scorpio. Later in the night, Flair competed in the BattleBowl, which was won by Vader.
- WCW Starrcade '93 = Flair defeated Vader to win the WCW World Title.
- WCW Clash of the Champions XXVI (January '94) = Flair and Sting fought in an "Elimination" Match against Vader and "Ravishing" Rick Rude. Flair was counted out. Sting was the "survivor".
- WCW Superbrawl IV ('94) = Flair kept his WCW World Title by defeating Vader in a "Thundercage" match, with The Boss as the Special Referee.
- WCW Spring Stampede '94 = Flair, the WCW World Champion at the time, wrestled to a No-Contest with Ricky Steamboat.
- WCW Slamboree '94 = Flair retained his WCW World Championship by pinning Barry Windham.
- WCW Clash of the Champions XXVII (June '94) = Flair both retained the WCW World Title and earned the WCW International Title from Sting. The two titles were unified by Flair.
- WCW Bash At The Beach '94 = Flair lost the WCW World Title to Hulk Hogan.
- WCW Clash of the Champions XXVIII (August '94) = Flair won, via countout, over the WCW World Champ Hulk Hogan.
- WCW Halloween Havoc '94 = Flair lost a "Steel Cage Retirement" Match to Hulk Hogan. Mr. T was the referee.
- NJPW Pyongyang Sports Festival (April 29, '95) = Flair was beaten by Antonio Inoki.
- NJPW Wrestling Dontaku '95 = Flair forced Hiroshi Hase to submit.
- WCW Slamboree '95 = Flair and Vader were defeated by Hulk Hogan and "Macho Man" Randy Savage.
- WCW Great American Bash '95 = Flair defeated "Macho Man" Randy Savage.
- WCW Bash At The Beach '95 = Flair lost a "Lifeguard Lumberjack" Match to "Macho Man" Randy Savage.
- WCW Clash of the Champions XXXI (August 4, '95) = Flair and Arn Anderson lost a "Handicap" Match to Big Van Vader.
- NJPW Sumo Hall (August 11, '95) = Flair fought to a Draw with Masa Chono.
- NJPW Sumo Hall (August 12, '95) = Flair forced Shiro Koshinaka to submit.
- NJPW Sumo Hall (August 13, '95) = Flair was pinned by Keiji Mutoh, eliminating him from the 1995 G-1 Climax Tournament.
- NJPW Sumo Hall (August 14, '95) = Flair defeated Hiroyoshi Tenzan.
- WCW Fall Brawl '95 = Flair was pinned by Arn Anderson.
- WCW Halloween Havoc '95 = Flair and Sting defeated Arn Anderson and Brian Pillman via DQ.
- WCW World War III '95 = Flair lost to Sting. Later in the night, Flair competed in the "3 Ring Battle Royal", which was won by "Macho Man" Randy Savage.
- WCW Starrcade '95 = Flair defeated Sting and Lex Luger in a "Triangle Match". Later, Flair beat "Macho Man" Randy Savage to win the WCW World Title.
- WCW Clash of the Champions XXXII (January '96) = Flair and the Giant defeated Hulk Hogan and "Macho Man" Randy Savage.
- WCW Superbrawl VI ('96) = Flair won the WCW World Title from "Macho Man" Randy Savage in a Steel Cage Match.
- WCW Uncensored '96 = Flair was part of the "Tower of Doom" Match with Arn Anderson, Meng, The Barbarian, Lex Luger, Kevin Sullivan, Ze Gansta, and the Ultimate Solution, against Hulk Hogan and "Macho Man" Randy Savage. Flair was defeated.
- WCW Slamboree '96 = Flair and "Macho Man" Randy Savage defeated Arn Anderson and Eddie Guerrero. The two later had to forfeit their match against Public Enemy.
- WCW Great American Bash '96 = Flair and Arn Anderson defeated Kevin Greene and Steve McMichael.
- WCW Bash At The Beach '96 = Flair won the WCW US Title from Konnan.
- WCW Hogg Wild '96 = Flair defended the US Title by defeating Eddie Guerrero.
- WCW Clash of the Champions XXXIII (August '96) = Flair won, via DQ, over then-WCW World Champ Hulk Hogan.
- WCW Fall Brawl '96 = Flair, teamed with Lex Luger, Arn Anderson, and Sting, lost a War Games match to Hollywood Hogan, Kevin Nash, Scott Hall, and the nWo Sting.
- NJPW Japan/US All-Star Tournament (September 19-23, '96) = Flair beat Tatsumi Fujinami, but lost to Kensuke Sasaki, who went on to win the Tournament.
- WCW Slamboree '97 = Flair, "Rowdy" Roddy Piper and Kevin Greene defeated the Outsiders (Kevin Nash, Scott Hall, and Syxx).
- WCW Great American Bash '97 = Flair and "Rowdy" Roddy Piper lost to the Outsiders, who retained their WCW Tag-Team Belts.
- WCW Bash At The Beach '97 = Flair was forced to submit to "Rowdy" Roddy Piper.
- WCW Road Wild '97 = Flair defeated Syxx.
- WCW Clash of the Champions XXXV (August '97) = Flair and Curt Hennig defeated Syxx and Konnan.
- WCW Fall Brawl '97 = Flair, teamed with Chris Benoit, Steve "Mongo" McMichael, and Curt Hennig, lost to Kevin Nash, Syxx, "Buff" Bagwell and Konnan in a War Games match.
- WCW Halloween Havoc '97 = Flair lost, via DQ, to WCW US Champion Curt Hennig.
- WCW World War III '97 = Flair was defeated by Curt Hennig, who retained his WCW US Title.
- WCW/nWo Souled Out '98 = Flair was forced to submit, losing the match against Bret "Hitman" Hart.
- WCW Boston Brawl (January '98) = Flair again submitted to Bret "The Hitman" Hart.
- WCW Starrcade '98 (December 27) = Flair, due to interference from Curt Hennig, was beaten by Eric Bischoff.
- WCW Souled Out '99 (January 11) = Ric and David Flair defeated Curt Hennig & Barry Windham.
- WCW Superbrawl IX (February 21, '99) = Ric was zapped by David Flair, allowing Hollywood Hogan to pin him and retain the World Heavyweight Title.
- WCW Uncensored '99 (March 14) = In a First Blood Cage Match for the World Title, Hogan rubbed barbwire on Flair's face, making him bleed. However, the referee did not end the match. Flair won, making Hogan submit to the Figure Four leglock and becoming the WCW World Champ.
- WCW Spring Stampede '99 (April 11) = Diamond Dallas Page, in a 4-way World Title Match, came away the winner over Hollywood Hogan, Sting, and Flair. DDP Diamond Cut Flair to become the champion.
- WCW Slamboree '99 (May 9) = Flair, with help from referee Charles Robinson, Arn Anderson, and his nurse, apparently defeated "Rowdy" Roddy Piper in a Control of the Company match. However, Eric Bischoff came out and awarded the victory to Piper.
- WCW Great American Bash '99 (June 13) = Flair won, via DQ, over "Rowdy" Roddy Piper, when Buff Bagwell attacked Flair. Flair retained the Presidency.
- WCW Halloween Havoc '99 (October 24) = Flair was beaten by Diamond Dallas Page in a Strap Match.
- WCW Superbrawl X (February 20, '00) = Flair defeated Terry Funk in a Texas Death Match.
- WCW Uncensored '00 (March 19) = Flair lost to Hulk Hogan in a Strap match.
- WCW Spring Stampede '00 (April 16) = Team Package (Flair and Lex Luger) defeated Johnny the Bull, Big Vito, Ron and Don Harris in a Handicap tag match, but lost to Shane Douglas & Buff Bagwell in a Tag-Team Title Tournament Final.
- WCW Slamboree '00 (May 7) = Flair was pinned by Shane Douglas.
- WCW Great American Bash '00 (June 11) = Flair forced his son David to submit.
- WCW Greed (March 18, '01) = Flair & Jeff Jarrett were beaten by Dusty & Dustin Rhodes.
- WWF Royal Rumble '02 (January 20) = Flair won a "Street Fight" over Vince McMahon.
- WWF Wrestlemania X-8 (March 17, '02) = Flair fell to the Undertaker in a "Street Fight".
- OVW Spring Break-Out '02 (April 5) = Ric & David Flair defeated Sean O'Haire & the Prototype.
- WWE Judgment Day '02 (May 19) = Flair & the Big Show lost a "Handicap" Match to Steve Austin.
- WWE King of the Ring '02 (June 23) = Flair defeated Eddie Guerrero.
- WWE Summerslam '02 (August 25) = Flair forced Chris Jericho to submit.
- WWE Unforgiven '02 (September 22) = Flair was beaten by the WWE Intercontinental Champion, Chris Jericho.
- WWE No Mercy '02 (October 20) = Flair was pinned by Rob Van Dam.
- WWE Backlash '03 (April 27) = Flair, Hunter Hearst Helmsley, & Chris Jericho won over Kevin Nash, Shawn Michaels, & Booker T.
- WWE Bad Blood '03 (June 15) = Flair defeated Shawn Michaels.
- WWE Armageddon '03 (December 14) = Flair & Batista won the "Tag-Team Turmoil" Match, which won them the WWE Raw Tag-Team Titles.
- WWE Royal Rumble '04 (January 25) = Flair & Batista kept the WWE Raw Tag Championships, winning a "Tables" Match over the Dudley Boyz.
- WWE Wrestlemania XX (March 14, '04) = Flair, Randy Orton & Batista won a "Handicap" Match over the Rock 'n' Sock Connection.
- WWE Backlash '04 (April 18) = Flair was beaten by Shelton Benjamin.
- WWE Vengeance '04 (July 11) = Flair & Eugene lost, via DQ, to the WWE Raw Tag Champs, La Resistance.
- WWE Unforgiven '04 (September 12) = Flair & Batista fell to Chris Benoit & William Regal.
- WWE Taboo Tuesday (October 19, '04) = Flair lost a "Steel Cage" Match to Randy Orton.
- WWE Royal Rumble '05 (January 30) = Flair competed in the Royal Rumble, which was won by Batista.
- WWE Unforgiven '05 (September 18) = Flair won the Intercontinental Title from Carlito.
- WWE Taboo Tuesday '05 (November 1) = Flair stayed the Intercontinental Champion, winning a "Steel Cage" Match over Triple H.
- WWE Survivor Series '05 (November 27) = Flair, as the Intercontinental Champion, lost a "Last Man Standing Non-Title" Match to Triple H.
- WWE New Year's Revolution '06 (January 8) = Flair, as the Intercontinental Champion, lost, via DQ, to Edge.
- WWE Royal Rumble '06 (January 29) = Flair competed in the Royal Rumble, which was won by Rey Mysterio.
- WWE Road To Wrestlemania Tournament (February '06) = Flair lost in the first round to the eventual winner, Triple H.
- WWE Wrestlemania 22 (April 2, '06) = Flair lost the "Money In The Bank Ladder" Match to Rob Van Dam. Matt Hardy, Shelton Benjamin, Bobby Lashley, and Finlay were the other participants.
- WWE Backlash '06 (April 30) = Flair was pinned by Umaga.
- WWE Vengeance '06 (June 25) = Flair won a "Three Falls" Match, via DQ, over Mick Foley.
- WWE Summerslam '06 (August 20) = Flair won an "I Quit" Match over Mick Foley.
- DSW Six Flags Park Slam (September 9, '06) = Flair defeated Montel Vontavious Porter.
- WWE Raw Family Reunion (October 9, '06) = Flair took down Mitch (of the Spirit Squad).
- WWE Cyber Sunday '06 (November 5) = Flair & Roddy Piper won the WWE Raw World Tag-Team Titles, defeating the Spirit Squad (Kenny & Mikey).
- WWE Survivor Series '06 (November 26) = Flair, Dusty Rhodes, Sgt. Slaughter, & Ron Simmons competed in an "Elimination" Match against the Spirit Squad (Johnny, Kenny, Mikey, & Nicky). Flair was the sole 'survivor'.
- WWE New Year's Revolution '07 (January 7) = Flair was pinned by Kenny Dykstra.
- WWE Royal Rumble '07 (January 28) = Flair competed in the Royal Rumble Match, which was won by the Undertaker.
- WWE Wrestlemania 23 (April 1, '07) = In a dark match, Flair & Carlito won a "Lumberjack" Match over Chavo Guerrero & Gregory Helms.
- WWE Judgment Day '07 (May 20) = Flair forced Carlito to submit.
- WWE Vengeance '07 (June 24) = Flair lost to the WWE United States Heavyweight Champion, MVP.
- WWE Royal Rumble '08 (January 27) = Flair took down MVP. Flair's career was on the line in this match.
- WWE No Way Out '08 (February 17) = Flair defeated Mr. Kennedy. Flair's career was on the line in this match.
- WWE Wrestlemania 24 (March 30, '08) = Flair lost a "Career Threatening" Match to Shawn Michaels. Due to the loss, Flair had to retire.
- RoH Stylin' & Profilin' (March 13, '09) = Flair appeared at the event, and was interviewed.
- TNA Lockdown '10 (April 19) = Team Flair (Desmond Wolfe, Sting, & Beer Money) lost a "Lethal Lockdown" Match to Team Hogan (Jeff Hardy, Jeff Jarrett, Rob Van Dam, & Abyss). Neither Flair nor Hogan officially wrestled in the match.
- TNA Victory Road '10 (July 11) = Flair fell to Jay Lethal.
- TNA Bound For Glory '10 (October 10) = Fourtune (Flair, Kazarian, AJ Styles, & Beer Money) lost a "Lethal Lockdown" Match to EV2.0 (Tommy Dreamer, Mick Foley, Stevie Richards, Raven, & Sabu).
- TNA Lockdown ’11 (April 17) = Immortal (Flair, Abyss, Bully Ray, & Matt Hardy) lost a "Lethal Lockdown" Match to Christopher Daniels & Fortune (Kazarian & Beer Money).
- WWE WrestleMania XXVIII (April 1, '12) = The Four Horsemen (Flair, Arn Anderson, Tully Blanchard, JJ Dillon, & Barry Windham) were inducted into the WWE Hall of Fame.
- NWA Mid-Atlantic Tag-Team Champion w/ Rip Hawk (7/04/1974 - 2/1975)
- NWA Mid-Atlantic Television Champion (2/08/1975 - 1975)
- NWA Mid-Atlantic Television Champion(2) (6/03/1975 - 6/10/1975)
- NWA Mid-Atlantic Heavyweight Champion (7/1975 - 7/26/1975)
- NWA Mid-Atlantic Heavyweight Champion(2) (9/20/1975 - 5/03/1976)
- NWA Mid-Atlantic Heavyweight Champion(3) (5/24/1976 - 9/11/1976)
- NWA Mid-Atlantic Heavyweight Champion(4) (10/16/1976 - 11/30/1976)
- NWA World (Mid-Atlantic) Tag-Team Champion w/ Greg Valentine (12/26/1976 - 5/08/1977)
- NWA Mid-Atlantic Television Champion(3) (4/04/1977 - 6/15/1977)
- NWA Mid-Atlantic Tag-Team Champion(2) w/ Greg Valentine (7/06/1977 - 8/22/1977)
- NWA United States Heavyweight Champion (7/29/1977 - 10/21/1977)
- NWA World (Mid-Atlantic) Tag-Team Champion(2) w/ Greg Valentine (10/30/1977 - 4/1978)
- NWA United States Heavyweight Champion(2) (4/09/1978 - 12/18/1978)
- NWA Mid-Atlantic Tag-Team Champion(3) w/ John Studd (10/30/1978 - 11/05/1978)
- NWA United States Heavyweight Champion(3) (4/01/1979 - 8/12/1979)
- NWA World (Mid-Atlantic) Tag-Team Champion(3) w/ Blackjack Mulligan (8/08/1979 - 8/22/1979)
- NWA United States Heavyweight Champion(4) (4/19/1980 - 7/26/1980)
- NWA United States Heavyweight Champion(5) (11/24/1980 - 1/27/1981)
- NWA World Heavyweight Champion (9/17/1981 - 6/10/1983)
- NWA Missouri Heavyweight Champion (7/15/1983 - 9/16/1983)
- NWA World Heavyweight Champion(2) (11/24/1983 - 3/21/1984)
- NWA World Heavyweight Champion(3) (3/23/1984 - 5/06/1984)
- NWA World Heavyweight Champion(4) (5/24/1984 - 7/25/1986)
- NWA World Heavyweight Champion(5) (8/07/1986 - 9/25/1987)
- NWA World Heavyweight Champion(6) (11/26/1987 - 2/20/1989)
- NWA World Heavyweight Champion(7) (5/07/1989 - 7/07/1990)
- WCW World Heavyweight Champion (1/11/1991 - 7/01/1991)
- NWA World Heavyweight Champion(8) (1/11/1991 - 3/21/1991)
- NWA World Heavyweight Champion(9) (5/19/1991 - 7/01/1991)
- WWF World Heavyweight Champion (1/19/1992 - 4/05/1992)
- WWF World Heavyweight Champion(2) (9/01/1992 - 10/12/1992)
- NWA World Heavyweight Champion(10) (7/18/1993 - 9/19/1993)
- WCW World Heavyweight Champion(2) (12/27/1993 - 4/17/1994)
- WCW World Heavyweight Champion(3) (4/24/1994 - 7/17/1994)
- WCW International World Heavyweight Champion (6/23/1994)
- WCW World Heavyweight Champion(4) (12/27/1995 - 1/22/1996)
- WCW World Heavyweight Champion(5) (2/11/1996 - 4/22/1996)
- WCW United States Heavyweight Champion(6) (7/07/1996 - 11/1996)
- WCW World Heavyweight Champion(6) (3/14/1999 - 4/11/1999)
- WCW World Heavyweight Champion(7) (5/15/2000 - 5/22/2000)
- WCW World Heavyweight Champion(8) (5/29/2000)
- WWE Raw World Tag-Team Champion w/ Batista (12/14/2003 - 2/16/2004)
- WWE Raw World Tag-Team Champion(2) w/ Batista (3/22/2004 - 4/19/2004)
- WWE Intercontinental Heavyweight Champion (9/18/2005 - 2/20/2006)
- WWE Raw World Tag-Team Champion(3) w/ Roddy Piper (11/05/2006 - 11/13/2006)
PWI Achievement Awards: (21 wins, 17 1st RUs, 10 2nd RUs, 11 3rd RUs)
- 1975 Rookie of the Year
- 1977 Most Hated Wrestler, 1st Runner-Up
- 1977 Match of the Year, 2nd Runner-Up (Flair vs. Andre the Giant)
- 1977 Tag-Team of the Year, 3rd Runner-Up (Flair & Greg Valentine)
- 1978 Most Hated Wrestler
- 1978 Match of the Year, 3rd Runner-Up (flair vs. Ricky Steamboat)
- 1978 Match of the Year, 1st Runner-Up (Flair vs. Blackjack Mulligan)
- 1979 Most Inspirational Wrestler, 1st Runner-Up
- 1981 Match of the Year, 1st Runner-Up (Flair vs. Dusty Rhodes)
- 1981 Wrestler of the Year
- 1982 Match of the Year, 1st Runner-Up (Flair vs. Bob Backlund)
- 1982 Wrestler of the Year, 1st Runner-Up
- 1983 Match of the Year (Flair vs. Harley Race)
- 1984 Match of the Year, 3rd Runner-Up (Flair vs. *unknown*)
- 1984 Match of the Year (Flair vs. Kerry von Erich)
- 1984 Wrestler of the Year
- 1985 Match of the Year, 2nd Runner-Up (Flair vs. Nikita Koloff)
- 1985 Wrestler of the Year
- 1986 Most Hated Wrestler, 1st Runner-Up
- 1986 Feud of the Year, 1st Runner-Up (Flair vs. Dusty Rhodes)
- 1986 Match of the Year (Flair vs. Dusty Rhodes)
- 1986 Wrestler of the Year
- 1987 Most Hated Wrestler
- 1987 Feud of the Year (Four Horsemen vs. Superpowers & Road Warriors)
- 1987 Match of the Year, 3rd Runner-Up (Flair vs. Ronnie Garvin)
- 1987 Match of the Year, 1st Runner-Up (War Games/The Match Beyond)
- 1987 Wrestler of the Year, 1st Runner-Up
- 1988 Feud of the Year (Flair vs. Lex Luger)
- 1988 Match of the Year, 1st Runner-Up (Flair vs. Sting)
- 1988 Wrestler of the Year, 3rd Runner-Up
- 1989 Most Inspirational Wrestler, 3rd Runner-Up
- 1989 Most Popular Wrestler, 1st Runner-Up
- 1989 Feud of the Year (Flair vs. Terry Funk)
- 1989 Match of the Year, 2nd Runner-Up (Flair vs. Ricky Steamboat)
- 1989 Match of the Year (Flair vs. Ricky Steamboat)
- 1989 Wrestler of the Year
- 1990 Most Hated Wrestler, 1st Runner-Up
- 1990 Feud of the Year (Flair vs. Lex Luger)
- 1990 Match of the Year, 1st Runner-Up (Flair vs. Sting)
- 1992 Most Hated Wrestler, 1st Runner-Up
- 1992 Feud of the Year, 1st Runner-Up (Flair vs. Randy Savage)
- 1992 Match of the Year, 2nd Runner-Up (Royal Rumble)
- 1992 Wrestler of the Year
- 1993 Comeback of the Year, 2nd Runner-Up
- 1994 Feud of the Year, 1st Runner-Up (Flair vs. Hulk Hogan)
- 1994 Match of the Year, 2nd Runner-Up (Flair vs. Hulk Hogan)
- 1994 Wrestler of the Year, 3rd Runner-Up
- 1995 Feud of the Year, 3rd Runner-Up (Flair vs. Randy Savage)
- 1996 Feud of the Year, 2nd Runner-Up (Flair vs. Randy Savage)
- 1996 Match of the Year, 3rd Runner-Up (Wargames)
- 1996 Wrestler of the Year, 2nd Runner-Up
- 1996 Wrestling Observer Hall of Fame Inductee
- 1997 Comeback of the Year, 3rd Runner-Up
- 1997 Most Popular Wrestler, 2nd Runner-Up
- 1998 Feud of the Year, 2nd Runner-Up (Flair vs. Eric Bischoff)
- 1999 Feud of the Year, 3rd Runner-Up (Flair vs. Hulk Hogan)
- 2008 Match of the Year (Flair vs. Shawn Michaels)
- 2008 Most Inspirational Wrestler
- 2008 Stanley Weston Lifetime Achievement Award