Ric Flair Dealt With Insecurity Through His Shawn Michaels WrestleMania Match And Beyond

The Ric Flair vs. Shawn Michaels match at WrestleMania 24 is widely regarded as one of the pre-eminent matches of the 21st century. And while the wrestling world will forever remember the closing moments, which saw Michaels apologizing to Flair before super-kicking him to retirement, "The Nature Boy" himself was unsure how the match was received by both his peers and fans.

While recounting the match on his "To Be The Man" podcast, Flair revealed how insecure he felt both before and after the match.

"I got very insecure as I got older because people kept telling me I was old," Flair said. "It made me insecure about my ability. Even though I could still perform, the age word kept hitting me so many different times, from so many different angles. When I came through that curtain, I know Shawn said, 'Man, that was great,' but I truly didn't know if it was good or bad. I knew it was highly emotional, the crowd was into it, and Shawn had just performed like nobody else — but when we walked back through that curtain, the entire company was there waiting for us. Not just the technical people, but the whole company was lined up through the hallway. 

"And then Shawn pulls me aside and says he wants to talk to me. I was afraid he was going to say that I messed up or didn't do something right. He then opens up his bag and pulls out two green boxes. They were Rolexes — unbelievable. It was a $65,000 watch. Shawn and I have the same watch. I didn't ask for it, this was just a kind gesture by Shawn."

Flair then detailed the mental hurdles he had to overcome to pull off the storybook ending to his match against Michaels on March 30, 2008.

"Even until the day I retired against Shawn, I never got over my confidence issues," Flair admitted. "It's hard to explain. Self-confidence is something you either have or don't. I just couldn't get myself to be the best I could be. When I realized I could be that person, because I didn't have any physical injuries, I'd go back to the locker room and say, 'I can't believe I was that guy the last five minutes of the match.' It's impossible to explain. Watch my 30 for 30 special, it says it all."

Long before his retirement bout against Michaels, Flair was in a rivalry with Mr. Perfect that seemed poised to end with a match at WrestleMania IX. However, the match fell apart after Flair returned to WCW, meaning WWE fans got to witness a prime Flair at the Grandest Stage of them All on only one occasion — at WrestleMania VIII against Randy Savage. While he eventually returned to WWE in 2002, Flair regrets not sticking around in Vince McMahon's promotion through the 1990s, as he believes such a move would have boded well for his legacy.

"I would have been in a demoted role [if I stuck around in 1993]," Flair said. "Vince came up to me and said, 'I'm gonna go young.' And that meant I wouldn't have been figured into his plans. I said, 'Thank you' and that initiated the Loser Leaves Town Match with Curt [Henning] on the second-ever episode of WWE Raw.

"In hindsight, I almost wished I stayed with WWE because it was such a disaster when I got back [to WCW]. If you think about it, one of the biggest mysteries ever in the history of this business is, how does WCW go broke? How is it possible with all that talent? It's just insanity."

Flair would eventually have WrestleMania matches against the likes of The Undertaker (WrestleMania X8) and The Rock & Mick Foley (WrestleMania XX), the latter as part of Evolution. Flair also participated in the Money in the Bank Ladder Match at WrestleMania 22.