10 Wrestlers Who Didn't Know When To Quit

3. Shawn Michaels

The Undertaker Quit
WWE

For almost a decade, Shawn Michaels DID know when to call it quits.

He lost to The Undertaker at WrestleMania XVI with his career on the line, then kept his promise to 'Taker that he wouldn't wrestle another match again... for eight years, at least.

With unbelievable paychecks coming from Saudi Arabia, the Heartbreak Kid saw dollar signs and decided the time was right for one last match.

But, his retirement had been perfect. They got around the issue with 'Taker by throwing him into the match as well. The Brothers Of Destruction had disrespected D-Generation X, so HBK was clear to have one more crack at the Deadman.

It sort of made sense, but Michaels had seen Triple H go through a lot from 2010-2018 and nothing had tempted him to return before. Fans saw right through it: HBK's gotta have his cash.

Shawn's come out and admitted he only returned for the money, that he was disappointed in the match, and that he definitely won't lace up his boots again.

It's just a shame the greatest retirement WWE had ever seen got ruined. He knew he was done for so long, but never say never when it comes to wrestling.

The funny thing about all of this is that HBK was the best wrestler in the match, even though he was the only person who hadn't wrestled in a long time.

He still had it, but he shouldn't have done it.

 
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When I'm not trying my hardest to visit all 50 U.S. states, I'm listening to music from the 80s, watching TV from the 90s, and reminiscing about growing up in the 00s. I'm currently living in Melbourne, Australia so WWE premium live events are on Sunday afternoons for me; the absolute dream.