The Undertaker is such a beloved figure in wrestling that it becomes easy to overlook his negative moments. Any wrestler to spend over three decades in WWE is bound to have a lot of deserving criticism for the worst moments of their careers. Undertaker had quite a few struggles on-screen and behind the scenes throughout the years in WWE.
Many fans and WWE personalities overlook the obvious negatives aimed towards Undertaker’s reputation. The retirement of Undertaker finally seems to be more certain, but the final chapters of his career added more negative memories. Any objective look at Undertaker’s legacy will witness the following memories and moments working against him in wrestling.
8. Weak Early History Of Bad WrestleMania Matches
The biggest piece of success for The Undertaker’s WWE legacy is his WrestleMania undefeated streak lasting over two decades. Undertaker ended up having classics in the 2000s with opponents like Edge, Randy Orton, Batista and Shawn Michaels.
However, the first few years of the streak meant very little in the grand scheme of WWE. Undertaker had weak matches against the likes of King Kong Bundy, Big Boss Man and Giant Gonzalez. The lackluster early few years of Undertaker’s takes away from the overall prestige when counting the early weak matches.
7. Failing With Nathan Jones
WWE wanted to elevate new talents by having them work with The Undertaker. Most feuded with the legend, but Nathan Jones received a unique opportunity as Undertaker’s protégé. WWE wanted Jones to gain credibility by learning from Undertaker and teaming up with him in tag bouts.
The duo of Jones and Undertaker were initially planned to continue Undertaker’s undefeated streak at WrestleMania 19 in tag action. WWE gave up on the idea by having Undertaker wrestle the match on his own defeating Big Show and A-Train. Jones was taken off television shortly after and dropped with no explanation for losing Undertaker’s partnership.
6. Million Dollar Corporation Faction Losing Steam Vs Him
The heel character of Ted DiBiase made him one of the most successful personalities of the Golden Era. WWE tried to keep benefiting from DiBiase’s reputation and talent by having him lead the Million Dollar Corporation faction after he retired from the ring.
The Undertaker was the main rival of the faction with lackluster results every step of the way. WWE even had a fake Undertaker character that led to an all-time bad SummerSlam 1994 main event. The awful feud is barely remembered despite hurting most talents involved in the feud.
5. Failed 2002 WWE Championship Reign
WWE turned The Undertaker heel when the American Badass version of his character needed a change. Vince McMahon instantly regretted going with the nostalgia story of Hulk Hogan winning the WWE Championship from Triple H after his epic WrestleMania 18 performance.
Undertaker was the heel to benefit from Hogan’s disappointing reign by taking the belt off him. Singles matches with Hogan and Triple H were viewed as terrible outings for Undertaker. The title reign was a flop until the great triple threat match with The Rock defeating Undertaker and Kurt Angle.
4. Betraying Paul Bearer For No Reason
One of the oddest storylines for The Undertaker saw him turning his back on Paul Bearer as a face. WWE booked Undertaker to return with the Deadman gimmick after Kane buried him alive to end the American Badass for good.
Bearer returned with Undertaker at WrestleMania 20 for a cool moment re-introducing the legendary character. However, Paul Heyman claiming that Bearer proved Undertaker had a weakness led to Undertaker burying Bearer in a concrete crypt. The sacrifice of ending his one ally just came off poorly since Undertaker never suffered from Bearer’s association in the past.
3. Taking Part In Failed Gimmick Matches
WWE tried a few new match concepts with The Undertaker involved as a major contributor. Undertaker was involved in the early stages of the Inferno match, Buried Alive and even the Punjabi Prison match to pay off various storylines.
None of those three match stipulations are still fixtures in the WWE landscape. Undertaker does get credit for his early involvement in the Hell in a Cell match, but WWE doesn’t ever discuss the negative scenarios of him trying to get new concepts over.
2. History Of Burying Talented Opponents
The Undertaker can help or hurt the career of his opponent when entering a feud. WWE has used Undertaker as a measuring stick for new talents to get a chance in either the main event scene or upper card picture.
Two major fan favorites were specifically made to look foolish against Undertaker. CM Punk had heat with Undertaker for not wearing suits as World Champion before losing the belt to the legend in one-sided match. Diamond Dallas Page received a worse case of getting decimated when Undertaker didn’t like him planning out their matches backstage.
1. Embarrassing His Legacy Too Many Times
WWE continued to bring The Undertaker back for the cheap pops and big money interest. Undertaker was involved in quite a few embarrassing matches over the past few years to negatively harm his overall legacy as an all-time great.
The Saudi Arabia shows have shown Undertaker’s price to take part in horrific matches like the botch fest vs Goldberg or the absurd Brothers of Destruction vs D-Generation X tag bout. Undertaker had some stinkers at WrestleMania as well against Roman Reigns and Bray Wyatt to take away from that chapter of his legacy.