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There's no denying the fact that The Undertaker has had one of the greatest WWE careers in the history of the company, something which many young Superstars can only dream of achieving. Being with WWE for nearly 30 years, and having entertained millions of his fans all over the world, The Undertaker should be very proud looking back at his career.
On the final chapter of WWE Network Special "Undertaker: The Last Ride", the Phenom seemingly announced his retirement from WWE, stating that at this point in his life, he doesn't have any desire to get back in the ring. Ever since the announcement, the wrestling world has been buzzing with fans, colleagues, and everyone in between thanking The Undertaker for everything that he has given to this industry.
If you ask The Undertaker he probably would not choose to change much about his legendary run. After all, what more can a man want? But turns out, there are certain moments, segments, and matches in his WWE career, that The Undertaker is not so proud of. He would certainly like to go to back and fix a few moments from his WWE past.
With that, let's take a look at the five biggest regrets of The Undertaker's WWE career. Be sure to comment down and let me know your most and least favorite moment of the Phenom's career.
Honorable Mention: The "train wreck" match against Goldberg at WWE Super ShowDown 2019.
#5 The Undertaker getting Sara's name tattoed on his neck
To every wrestling fan who has not watched WWE Network's The Last Ride, the documentary fittingly portrays the massive impact that The Undertaker's wife Michelle McCool has had on her husband's life. However, long-term fans know that she wasn't always the "lady love" in the Phenom's life.
Before The Undertaker started a relationship with McCool, he had already been married twice previously. At one time, he was very much in love with his second wife Sara, as evidenced by the famous tattoo of her name that The Undertaker had on his neck. Getting a permanent tattoo is a painful process, especially when you get it on your neck as the skin there is much more delicate than, for example, your arm or thigh.
The Undertaker decided to get the tattoo of her wife Sara's name on his neck. This was in the early 2000s when the two started appearing on WWE programming together with The Undertaker portraying a more humanized version of himself. Unfortunately, the relationship didn't last, as the two divorced in 2007. The Undertaker went on to replace his neck tattoo with the names of his two daughters.
#4 The Undertaker's disastrous WrestleMania 33 match with Roman Reigns
As evident in the first chapter of The Last Ride docuseries, The Undertaker was very disappointed with his WrestleMania 33 match against Roman Reigns. He mentioned that he planned that to be his last match. However, after rewatching the main event match, The Undertaker was so disappointed that he refused let the bout be his last match. Hence, he came back for redemption!
During a recent interview, The Undertaker spoke about his WrestleMania 33 match.
"The Roman Reigns match at WrestleMania was tough. I was not just disappointed for me, I was disappointed for Roman Reigns as well. It was my opportunity to give him something that will push him to a higher level. And I didn’t deliver on that. And I can’t make excuses. Yes, I was banged up and beat up but I was there. In my mind, I had a responsibility. If my name is on the page, then you gotta go. I knew in January that I was physically not going to be at my best but it was too late at that point. Like, I have already committed, it’s already been planned and this is what is going to happen. And I was scrambling, trying to figure out how I am going to make this work. And, I was thoroughly disappointed."
While the match in itself was a forgettable one, The Undertaker's symbolic "retirement" after the match was one of the more memorable moments in recent WWE history. Of course, we all know that The Undertaker came back a year later!
#3 The Undertaker hanging the Big Boss Man
Back in the day, WWE was known to do some crazy things on its TV programming, something that would be unthinkable in the PG era. One such moment took place at WrestleMania 15 in 1999, where The Undertaker took on the Big Boss Man inside Hell in a Cell. While the match in itself wasn't one of the better ones in The Undertaker's career, what happened afterward made for one of the most uncomfortable moments in WWE history.
For those that have not seen it, The Undertaker went on to hang the Big Boss Man from the cage by a noose, in front of thousands of people in the arena, not to mention the millions watching at home. While it might sound like a cool idea on paper to further establish the dangerous and deadly character of the Phenom, hanging his opponent on a live pay-per-view was a little too much.
Bruce Prichard later revealed that the Big Boss Man was wearing a harness under his outfit that they hooked him onto. However, this still doesn't justify WWE trying to pull off that segment!
#2 The Undertaker putting over some questionable "Superstars"
The Undertaker has long been a WWE locker room leader. So much so that the WWE roster made him the judge of the famous "wrestler's court" that used to be held backstage on occasion. This is just one of the many signs of the massive respect every WWE Superstar had for him.
In the final chapter of The Last Ride, Randy Orton mentions how The Undertaker helped put him on the map by selling his moves during their first match together, even when Vince McMahon had not approved it. While putting over new talent is seen as a responsibility of established names like The Undertaker, it is not something that should be done lightly.
Fans rarely saw The Undertaker taking a loss, and whenever he did taste defeat, the Superstar picking up the victory usually received a massive boost. Take, for example, Brock Lesnar, who rose to a different level of stardom after breaking The Undertaker's streak at WrestleMania 30.
With that said, there are a few losses in The Undertaker's career that didn't end up serving any purpose. Once such instance of this occurred when Vladimir Kozlov pinned The Undertaker clean in February 2009 on SmackDown. Now, I won't be surprised if many of you don't know who Vladimir Kozlov is - as he did not go on to have a very impressive career. Even at the time, there is no denying that he was not ready to be pushed in such a massive way.
A similar story unfolded when The Great Khali destroyed The Undertaker at Judgement Day 2006. Is he a giant? Yes. Is he larger than The Undertaker? Yes. But that didn't justify him going over the Phenom in such an emphatic manner. The decision looked even more questionable once WWE started using him in comedy segments a little while later.
#1 The Undertaker's encounter with Giant Gonzalez
The Undertaker's WrestleMania streak is one of the greatest achievements by a Superstar in WWE history. He has had numerous amazing matches at the "Show of Shows", with his encounter with Shawn Michaels at WrestleMania 25 hailed by many as the greatest WWE match of all time.
Unfortunately, in the earlier years of the streak, he had a disastrously bad WrestleMania encounter against Giant Gonzalez. As large as Giant Gonzalez was, he wasn't known for his wrestling abilities. This led to what many consider to be the worst match on The Undertaker's WrestleMania resume.
Recently, The Undertaker appeared on the Not Sam Wrestling Podcast and discussed his experience of working with Giant Gonzalez.
“It was hideous. It was so bad on so many levels. I would be in much better shape now if I would have skipped that one program. As physically demanding as it was, it was twice the mental strain."
"You had Bret there, Yoko there. All these guys are going out having these great matches. You want to be mentioned in the same breath as those guys. It was not possible. It was survival every night trying to figure out what he could do. At that time, I didn’t sell a lot or bump around. It did help me and prepare me later on for being able to work with people.”
The match is also famous for being the only match during The Undertaker's WrestleMania streak that he won by disqualification!
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