Five things The Undertaker did wrong by prolonging his career

WWE, The Undertaker (Photo credit should read AMER HILABI/AFP/Getty Images)
WWE, The Undertaker (Photo credit should read AMER HILABI/AFP/Getty Images) /

If you close your eyes and think back to WrestleMania XXX, you might still see the shocked fan with his mouth hanging halfway to the floor following The Undertaker and Brock Lesnar match. This was the night “The Streak” was slaughtered.

The opinions have varied since this match took place. Some say The Undertaker’s undefeated streak should have never been compromised. Some say a superstar other than Lesnar should have been awarded the honor.

Wherever you stand, we can’t rewrite history. And it’s Lesnar’s name that is now synonymous with the ending of this prestigious streak. But what did this all mean for The Undertaker’s career? Should it have ended right then and there?

When should The Undertaker have ended his in-ring career?

Leaving WWE after losing once at WrestleMania wouldn’t have been the right way to leave. But leaving after losing a second time would have been the right call. Possibly even after WrestleMania 31, when The Undertaker returned to face Bray Wyatt.

Having Wyatt go over that night would have strapped a rocket to his sweaty swamp back. And having The Undertaker lose two years in a row would play into the perfect retirement. An old gunslinger can’t lose two duels in a row and stick around the town.

But The Undertaker won and moved on to Shane McMahon, having an unnecessary Hell in a Cell match the following year. This was followed by a match with Roman Reigns, a sloppy encounter that saw The Undertaker take his second loss at “The Show of Shows”.

He even left his gear in the ring, indicating to the fans that he had wrestled his last match. And for the year that followed, this was the predominant belief…until John Cena called out The Undertaker and was squashed in a quick match.

The following year at WrestleMania 35, The Undertaker was left off the card, fueling more retirement speculation. But of course, he wasn’t done. There was one more WrestleMania match to be had. This time with AJ Styles.

On paper, it seemed Styles could make The Undertaker look good in the ring, despite his aging body and slower pace. But then the pandemic changed everyone’s plans, and we got a mini-movie version of The Undertaker and Styles instead of an in-ring bout.

And this is where it ended for The Undertaker. Riding off from a movie set on his motorcycle. An anticlimactic end to an unmatched career. It just didn’t feel right. Why didn’t The Undertaker leave much sooner? Let’s explore a few reasons.

Undertaker Hurt His Own Mystique

At WrestleMania 33, Roman Reigns managed to do what only one other person had done: defeat The Undertaker at the biggest show of the year. That night, Reigns joined Brock Lesnar and formed a very exclusive club.

But the match itself was a shell of what it could have been, and not because of Reigns. The blame for this bore of a main event falls squarely on The Undertaker’s shoulders. He was out of shape and seemed to be a step behind Reigns the entire time.

As a result, The Undertaker looked human. The aura of unstoppable other-world dominance was practically dead, and that’s because The Undertaker was already two years overdue for retirement. Going out on his back for Wyatt was the way to go.

Undertaker Helped Tarnish a Legacy

From stuffing Rusev into a casket to squashing AJ Styles, the Saudi Arabia shows provided nothing from The Undertaker character that we hadn’t seen before. The gong, the pop, the walk. The post-match kneel and salute.

It was during one of these shows that WWE convinced Shawn Michaels to come out of retirement to team with Triple H and take on The Undertaker and Kane, collectively known as The Brothers of Destruction.

Following a storybook back-to-back WrestleMania career-ending ordeal, Michael returned sloppy, bald, and battered. Of course, the legacy of Michaels would not have been tarnished had The Undertaker retired years earlier.

He Played a Part In Stealing Spots

How many more dives will Shane McMahon take before it’s enough? The son of Vince is seemingly willing at a moment’s notice to get involved in a feud that will lead to him taking a hard bump along the way and stealing spots from deserving superstars.

At WrestleMania 32, McMahon faced The Undertaker, inside Hell in Cell, for no real reason at all. While it was nice to see McMahon back on screen after an extended absence, his inclusion on the WrestleMania card was unnecessary.

As usual, McMahon was looking to make a literal splash and jumped from the top of the steel structure. A spot we didn’t need, and a spot anyone who isn’t a spot junkie didn’t want. This match was on the main card while The Usos were on the pre-show.

He Ruined His Own Farewell

While it really feels like The Undertaker should have retired after WrestleMania 31, coming back for two more events can almost be forgiven if he would have actually walked away after leaving his gear in the ring.

Despite how bad the match was, Roman Reigns going over on The Undertaker was still a big deal. And having Reigns claim the ring as his yard the following night was a nice touch. The new gunslinger in town put down the old cowboy.

But the moment was ruined when The Undertaker returned a year later. A strong send-off from a sound barrier-breaking stadium was all tossed aside for a man’s pride. When it’s time to go, it’s time to go, but The Undertaker just didn’t get the note.

He Ended His Career On a Movie Set

Obviously, no one could have predicted the arrival of this pandemic. And while professional wrestling continued to operate during the crisis, it was clear that every company was going to struggle through this unexpected scenario.

The Undertaker facing AJ Styles was likely strategic. If anyone could have made The Undertaker look half-decent in the ring, it would have been Styles. But due to the situation, we got this match in the form of a high-budget student film.

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And while riding off on a motorcycle to Metallica playing in the background is an old-school kind of cool, this is the lasting image of The Undertaker’s final match. Roll sound. Action. Cut. That’s a wrap.