The Undertaker’s 10 Biggest Regrets In His WWE Career

7. Failing To Help The Locker Room

There’s a perception of The Undertaker as a fair man, but in many ways he was one of the most political operators in WWE. He was very friendly with Vince McMahon, to the point that not even Shawn Michaels and the kliq would mess with him. Taker wielded power and used it to full effect.

This was fairly obvious to anyone watching WWF television. The Undertaker almost never lost. When he did, it was usually due to screwy shenanigans. It was a conscious choice by Calaway, that he didn’t want to be seen as weak. It partly explains why he put over Brock at Mania 30, as he only wanted to be seen as beatable by legitimate tough guys.

This sort of attitude was unhelpful. The Undertaker could’ve put over a lot more younger talent and made a lot more stars in his WWE run. He might one day regret not helping a more broad range of talent reach their potential.

You also have to consider the squashes he performed. He seemed to take glee at decimating the WCW roster intake during 2001, helping to devalue Vince McMahon’s investment in the process. One day he might look back and wish he’d been a little more generous.