Most fans and wrestlers consider The Undertaker one of the most respected wrestlers in the WWE locker room. However, there was a time when, despite his reputation, he wasn't able to stop one of the most infamous moments in professional wrestling history.
Undertaker appeared on Bill Simmons' podcast this past week to promote his documentary The Last Ride, and while he was there he talked about the infamous Montreal Screwjob. According to Undertaker, he was furious the day after the Montreal Screwjob and was headed to Raw to rip into someone over how the entire thing went down.
As a quick reminder, Bret "The Hitman" Hart was WWE Champion but had just signed with WCW. He was on his way out out of the company, and Vince McMahon wanted him to drop the title to Shawn Michaels at Survivor Series.
The match was in Hart's hometown, and he did not want to lose to his rival Michaels, especially not in front of a hometown crowd. Hart had the idea to have the match end controversially, and either be stripped of the title or vacate it the next night on Raw. Instead, Vince McMahon screwed over Hart by calling for the bell when Michaels had him locked in the Sharpshooter — Hart's finishing move — and the rest is history.
Hart left angry and didn't speak to Michaels or McMahon for almost a decade. Undertaker said that he felt he could have helped and everything could have ended on better terms. According to the Dead Man in the podcast episode, he was willing to talk to Hart and work the match in place of Michaels. Undertaker said he believes Hart would have lost to him at Survivor Series with no complaints. Undertaker was willing to go on Raw the next night or the following PPV and drop the title to Michaels.
Undertaker let Simmons know that he was angry at how the entire situation went down, and wishes he had gone to McMahon to tell him his thoughts because it could have resolved all of the problems peacefully. As it was, Undertaker said the entire controversy dragged down the locker room with the drama, and he wishes he could have stopped the bad blood that built up between WWE and members of talent.
Honestly, this could have been easy to set up Undertaker's plan from the start. Hart won the WWE title from The Undertaker at SummerSlam, three months before the Survivor Series PPV. When it came time for the infamous event in Montreal, WWE had Undertaker battle Michaels at Badd Blood: In Your House to determine the number one contender for Hart's title. Badd Blood was the Hell in a Cell match that saw Kane arrive in WWE for the first time, storm into the cage, and cost Undertaker his title opportunity.
Kane had his debut match against Mankind at Survivor Series, and Undertaker was not on the card at all. Undertaker refused to wrestle his brother in storyline, and WWE could have given him the title match instead of Michaels by pitting the two men in another match due to Kane's interference in the first one. Undertaker could have won the title at Survivor Series, and then the next night on Raw, Kane could have attacked again and cost him the title, making 'Taker the perfect transition champion to get the belt to Michaels. Undertaker and Michaels kept feuding until the end of the year anyway, so there is no reason this couldn't have replaced the entire fallout that resulted from the Montreal Screwjob.
"I think I could’ve helped this whole thing out," Undertaker said. "I’m right here, and you know I’m going to do business. But it happened, and I was really pissed."