Fliehr was born on February 25, 1949 in Memphis, Tennessee. His birth name is widely perceived to be Fred Phillips, although on different documents, he is also credited as Fred Demaree or Stewart, while his biological parents were Luther and Olive Phillips (the latter of which was also credited under the Demaree and Stewart surnames). He was adopted, and at the time of his adoption (arranged by the Tennessee Children's Home Society), his father, a physician, was completing a residency in Detroit. Shortly afterward, the family settled in Edina, Minnesota, where the young Fliehr lived throughout his childhood and after ninth grade he attended Wayland Academy, a coeducational boarding school in Beaver Dam, Wisconsin, for four years (five years total in high school), during which time he participated in interscholastic wrestling, football and track.

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.

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