WWE‘s The Last Ride continues to reveal intimate details about Mark Calaway’s career as the Undertaker, highlighting the ups, downs, and of course, the regrets. It’s interesting that the docuseries doesn’t just address important moments in his superstar tenure, but also gives Calaway’s perspective on industry stalwarts such as Vince McMahon and other wrestlers that help keep the business ticking.
In the third chapter, “End of an Era,” ‘Taker digs deep into his feelings on one of his biggest rivals and surprises fans with the shocking revelation that he’s actually jealous of him. It’s none other than the Heartbreak Kid, Shawn Michaels, and it has to do with Michaels’ retirement.
The Dead Man and Michaels had a badass rivalry in the Attitude Era which culminated in back to back WrestleMania matches in 2009 and 2010. After the first one, fans were so enthralled that a second one was booked for WrestleMania 26, with ‘Taker putting his Streak on the line against Michaels’ career. The match more than delivered, with Undertaker retiring HBK in another amazing encounter. However, that match still haunts the Phenom to this very day, as he remains envious of how Michaels walked away and stayed mostly retired.
“I’m so envious of Shawn because he was able to walk away and be good with it. Do I wish I had that kind of clarity? Absolutely,” Undertaker admits. “He had the clarity before going into the match. Hopefully, when I have the match I’m looking for, I have that clarity. ‘Okay, that’s it.'”
It’s something that earlier episodes touched on, with his wife Michelle McCool believing that ‘Taker often feels like a tumbleweed in the wind. When he has awful matches like the one against Roman Reigns, he’ll want redemption, but when he has good ones, like the match against John Cena that followed, he’ll want to continue. Edge also spoke about this earlier, suggesting it’s a Catch-22 that keeps many wrestlers moving forward. Michaels actually corroborates that feeling, speaking about how he knew he wanted out, but continued success could be the downfall for personalities like the Dead Man.
HBK agrees it’s a double-edged sword and somewhat of an addiction for Undertaker, with Triple H also echoing the same sentiment in the docuseries. The “peace and closure” Michaels has eats away at Undertaker, and he confesses he just can’t get that one final, perfect match to bring the curtains down. Triple H also admits the same temptation is there with other wrestlers, like himself, but HBK’s the only one who was sure enough to really walk away. That is, until he and Triple H beat ‘Taker and Kane at Crown Jewel in 2018, which was more a one-off nostalgic showcase than anything else.
Michaels understood where the Dead Man was coming from, as seen from some comments he made on The Bump. “It was a sign of him, a vulnerability that nobody knows about, and I understood that,” HBK reveals. “Because he was only doing, and I don’t mean only, but he was already just doing one a year at that time in a very limited schedule and most people really enjoy doing that and can do that for quite some time. So, I understood the comment, I was struck by the tone of it.”
It’s clear there’s a mutual respect between both legends, as Michaels was comfortable knowing he wanted more time with family and religion and was ready to walk away from the ring. As for the Dead Man, while he might envy Michaels’ peace in retirement, McCool has no clue when he’ll want to end it. While the day will come when the Undertaker will truly have his last match, it seems that WWE will have to drag Calaway in a box to really make him leave sports entertainment behind forever.
WWE's The Last Ride reveals Undertaker is jealous of Shawn Michaels because of one significant and sentimental WrestleMania moment.