5. He Was Supposed To Main Event WrestleMania 8 With Hulk Hogan
When Flair jumped to WWE towards the end of 1991, a lot of people assumed that WWE would do the obvious thing and have him headline WrestleMania 8 against Hulk Hogan. Flair was the top heel in NWA/WCW for many years before that, so the assumption was that he was brought in to feud with Hogan. When Flair cost Hogan the WWE Title in his match against Undertaker at Survivor Series 1991, the thinking was that it would lead to Hogan vs. Flair at WrestleMania 8. I was 11 years old at that time and even I thought that. The Hogan/Flair match didn't happen at WrestleMania or any other WWE televised show. Both men were a part of the 1992 Royal Rumble with the WWE Title on the line, but it was Flair that emerged the winner. Hogan ended up feuding with Sid Justice as a result of what happened and Randy Savage ended up being built up as Flair's challenger. In an
interview with JJ Dillon a few years back, he spoke about WWE's thinking at the time. Dillon worked in the WWE office at that point and worked closely with Vince McMahon in the early 1990s: "You would've thought it would've been a natural dream match. It didn't have the box office sizzle that we all would assume that it would. And after a run that was disappointing in markets (like Tampa) where it should have done well and it didn't... it's like Vince (McMahon) said - that match got booked 5 years too late." Dillon's comments suggest that if they had brought Flair into WWE in the late 1980s that WWE would have been willing to do it, but they felt like Flair in 1992 wasn't the right opponent for Hogan. McMahon loved booking Hogan against bigger opponents like Undertaker and Sid, so perhaps that was his thinking. As the bigger wrestler, Hogan may have been booed by fans that were already starting to boo Hogan at that point. In the end, WrestleMania 8 ended up as a great show with the Flair/Savage match as the best match on the card and the ending of Hogan/Sid was awesome because the Ultimate Warrior came back to save Hogan from a heel beating. It should be noted that when Hogan went to WCW in 1994, they promoted several Hogan/Flair matches on television and PPV. They sold out arenas and did big business for a growing company.