During an interview with Steve Austin on the “Broken Skull Sessions,” Flair talked about his run in WWF in the early 2000s and said he was perhaps at his lowest point in terms of self confidence. Flair admitted it was hard to fit in with the rest of the locker room because he was so much older than everyone else.
That all changed when Flair faced off against The Undertaker at WrestleMania 18 and at first, Flair admitted that he was surprised hearing that was going to be his match.
“He made me. There’s only two guys that made me in the business, plus Shawn [Michaels] at the end: he and Harley Race. If Harley hadn’t showed up for Starrcade, the event would have been dead but then he wouldn't have made. When I was at the worst possible point of self-confidence, [Triple H] came to me and said, ‘Taker wants to work with you at [WrestleMania] 18.’ I said, ‘Taker does?’ I couldn’t believe it,” Flair said.
Flair would go on to say that he was having doubts in regards to his abilities even as he was walking down the ring for the WrestleMania match. Those doubts were erased by the time the match ended.
“I’m going yeah, but I’m thinking how can I pull this off? I still didn’t have [the confidence]. Even when I was going down to the ring, I still wondered. [After the match], I walked to the back and Jack Lanza said, ‘You pulled it off you son of a bitch,’” Flair said.
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