The Undertaker’s 10 Biggest Regrets In His WWE Career

10. The WrestleMania 30 Match With Brock Lesnar

The most immediate example of regret in Undertaker’s life is surely the WrestleMania 30 loss to Brock Lesnar. This was not the grand finale that the two decade streak narrative deserved. It was, in fact, a sad whimpering conclusion to what had been one of the greatest wrestling storylines of all time.

The streak was initially born out of coincidence. The Undertaker simply didn’t like doing many jobs. It wasn’t until WrestleMania X8, when WWE started referencing a “decade of destruction”, that the idea of the streak story was realised. By WrestleMania 21, against Randy Orton, the question of “can Undertaker’s opponent end the streak?” was key in the sales of the show. It would remain that way for the next nine years.

The longevity of the streak makes it all the more disappointing that the big payoff was a poorly promoted and poorly executed match against a part timer. In retrospect, The Undertaker must regret the 2014 debacle.

A concussion he suffered early in the match didn’t help. But even if it had been a stellar performance, the build up had still been really weak. Add into that all the debates of if the streak should ever have ended and who was the right man to end it. The general conclusion is that WWE and The Undertaker were disappointed with the way things went.