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The Undertaker Admits He Should Have Retired With Shawn Michaels

Over the last few years, the talk around The Undertaker has concerned his eventual retirement from wrestling. Although he’s no longer partaking anywhere near a full-time schedule, The Deadman has continued to stay in the ring at least once a year over the last few go-arounds. The WWE documentary titled Undertaker: The Last Ride centered around these last few years of his career has given him more insight into his internal thinking concerning his status with his in-ring career. The Undertaker recently voiced that one of his biggest regrets in that regard involved fellow all-time great Shawn Michaels.

The Undertaker’s retirement talk

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It has become blatantly apparent that The Undertaker is on his last legs in his illustrious career that spans nearly three decades.

The 55-year-old has pushed around the talk of retirement over the last few years. Still, he has continued to participate in matches at WrestleMania and the Super ShowDown over the previous couple of go-arounds. His initial hope was that his match against Roman Reigns at WrestleMania 33 would be his last, but that didn’t wind up how he wanted and has led him to continue to wrestle.

That has left the dialogue open in terms of when he will finally step away from the squared circle to wrap up his incredible career. With that in mind, he did recently open up as to one regret he had in that aspect that has revolved around another WWE legend.

The Undertaker believes should have retired with Shawn Michaels

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The Undertaker has garnered much of his prestigious allure behind his tremendous success at WrestleMania.

One of his legendary matches occurred at WrestleMania 26 against Shawn Michaels, who put his career on the line. It turned out to be an iconic showing between the two that The Undertaker voiced during the fourth episode of Undertaker: The Last Ride documentary that he should have retired with Michaels after that match. (H/T Essentially Sports)

“Shawn and I have talked quite a bit, and well, I’ve said on more than one occasion-I should have left with you.”

Michaels was nearing the end of his career and had decided the year before at the WWE Slammy Awards the year before to make that his final match. Although that match didn’t top what the two legends put forth at WrestleMania 25, it was a high note that Michaels could gracefully go out on to end his time in the ring.

Meanwhile, the Undertaker is still searching for that match that he can have peace in his mind with that will let him retire.

How much longer will The Undertaker wrestle?

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It’s often quite difficult for wrestlers to finally step away from the business as many all-time greats hold on too long.

The Undertaker may not have reached that point, but there’s no telling if he can put on a high-caliber performance to his liking that he can feel completely satisfied with stepping away from the ring. He is coming off an impressive Boneyard match against AJ Styles at WrestleMania 36, which provides him confidence that he can still put out a strong showing at his craft.

There isn’t any indication if he will wrestle at WrestleMania 37, but he has left that door open. He did voice that it will have to take a “juicy” storyline for him to get back into the ring. Ultimately, it all depends on The Undertaker being able to go out on his terms with a match that can gracefully wrap up his career as it did for Michaels a decade ago.