Flair signed with the World Wrestling Federation (WWF) in September 1991 and began appearing on television with the Big Gold Belt, calling himself "The Real World Champion". Led by his "financial adviser" Bobby Heenan and his "executive consultant" Mr. Perfect, Flair repeatedly issued challenges to WWF wrestlers like "Rowdy" Roddy Piper and Hulk Hogan, wrestling a team led by Piper at Survivor Series in November 1991 and helping The Undertaker defeat Hogan for the WWF Championship that same night. WCW sued Flair in an attempt to reclaim the championship belt, but Flair claimed that he owned the title belt in lieu of the US$25,000 deposit paid by NWA champions upon winning the title, which had not been returned to him when he was fired from WCW.  At the 1992 Royal Rumble, Flair won the Rumble match to claim the vacant WWF Championship. Flair entered as number three in the Rumble match and lasted 60 minutes, last eliminating Sid Justice with help from Hulk Hogan, who had been eliminated by Justice seconds earlier. Randy Savage then challenged Flair for the WWF Championship as part of the double main event at WrestleMania VIII. In the storyline, Flair taunted Savage by claiming that he had a prior relationship with Savage's wife, Miss Elizabeth. Savage defeated Flair for the title at WrestleMania. In July 1992, as Savage prepared to defend the title against The Ultimate Warrior at SummerSlam, Flair and Mr. Perfect sowed distrust between the two by suggesting that they would back one or the other during their match. They actually attacked both Savage and Warrior and injured Savage's knee, an injury that Flair exploited to regain the title in a match with Savage on September 1. His second reign was short-lived, however, as he lost the title to Bret Hart on October 12, 1992.  Flair teamed with Razor Ramon to take on Savage and Perfect at the Survivor Series in November 1992. Flair appeared in the Royal Rumble in January 1993, then lost a Loser Leaves the WWF match to Mr. Perfect on the next night's (January 25) Monday Night Raw in a match taped six days earlier. Flair then fulfilled his remaining house show commitments, making his last appearance on February 10, 1993, before returning to WCW.  Once again as a top fan favorite, Flair played a major role in the New World Order (nWo) invasion storyline in late 1996 and throughout 1997. He and the other Horsemen often took the lead in the war against Scott Hall, Kevin Nash, and Hollywood Hulk Hogan, whom Flair immediately challenged for the WCW World Heavyweight Championship at the Clash of the Champions XXXIII, but won only by disqualification. In September 1996, Flair and Anderson teamed with their bitter rivals, Sting and Lex Luger, to lose to the nWo (Hogan, Kevin Nash, Scott Hall, and an impostor Sting) in the WarGames match at Fall Brawl when Luger submitted to the impostor Sting's Scorpion Deathlock.  In October 1996, two developments occurred that affected the Four Horsemen when Jeff Jarrett came over to WCW from the WWF, and expressed his desire to join the Horsemen as he immediately gained a fan in Ric Flair, much to the chagrin of the other Horsemen. Flair finally let Jarrett join the group in February 1997, but the others did not want him, and in July 1997 was ultimately kicked out of the group by Flair himself, who had enough of the instability Jarrett's presence caused the Horsemen. Flair also feuded with Roddy Piper, Syxx, and his old nemesis Curt Hennig in 1997, after Hennig was offered a spot in The Four Horsemen only to turn on Flair and The Four Horsemen at Fall Brawl in September 1997, in which Hennig punctuated the act by slamming the cage door onto Flair's head.  In April 1998, Flair disappeared from WCW television, due to a lawsuit filed by Eric Bischoff for no-showing a live episode of Thunder on April 16, 1998 in Tallahassee, Florida. After the case was settled, Flair made a surprise return on September 14, 1998 to ceremoniously reform the Four Horsemen (along with Steve McMichael, Dean Malenko, and Chris Benoit). Flair feuded with Bischoff for several months afterward. Flair repeatedly raked Eric Bischoff's eyes during this feud. This culminated in a match at Starrcade between Bischoff and Flair in December 1998, which Bischoff won after interference from Curt Hennig, a former member of the Four Horsemen. The following night in Baltimore on Nitro, Flair returned and threatened to leave WCW, demanding a match against Bischoff for the presidency of the company. The match was made, and despite the nWo interfering on Bischoff's behalf Flair won and was granted the position of president of WCW. This resulted in a match at Superbrawl between Flair and Hollywood Hogan for the WCW Championship, which Flair lost after being betrayed by his own son David Flair.  In spite of his son's betrayal, Flair signed a rematch at Uncensored which was billed as a First Blood barbed wire steel cage Match against Hogan where Flair's presidency and Hogan's WCW World Heavyweight Championship were on the line. Despite being the first to bleed, Flair won the match by pinfall thanks to the bias of the referee Charles Robinson, who counted Hogan out.  As on-air WCW President, Flair began abusing his power much like Bischoff had, favoring villains over fan favorites and even awarding the WCW United States Heavyweight Championship (which was vacated by Scott Steiner due to injury) to his son David and resorting to whatever means necessary to keep him as United States Heavyweight Champion. Flair eventually formed a stable of followers which included Roddy Piper, Arn Anderson and the Jersey Triad to keep things in order. Flair's reign as president came to an end on the July 19 episode of Nitro, when he faced and lost to Sting for the position. During the course of the match, Sting had Flair in his Scorpion Death Lock, but with the referee knocked unconscious, no decision could be reached. A returning Eric Bischoff came to the ring and began ordering the timekeeper to ring the bell, which he eventually did, awarding the match and the presidency to Sting (who promptly gave it up upon receiving it).  Flair won his last world titles in his career by winning the WCW World Heavyweight Championship twice during 2000, the company's last full year of operation. When WCW was purchased by the WWF in March 2001, Flair was the leader of the villainous group called the Magnificent Seven. Flair lost the final match of Nitro to Sting, recreating the second match of Nitro in 1995. Nevertheless, Flair has repeatedly stated in various interviews how happy he was when WCW finally closed down, although at the same time the fact that many people would lose their jobs saddened him.

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