#1 Vince McMahon never wanted The Undertaker vs. Shawn Michaels
Looking back at the last three decades of WWE programming, very few rivalries have reached legendary status in the same way that The Undertaker vs. Shawn Michaels has.
The two men competed in the first Hell In A Cell match at In Your House: Badd Blood in September 1997 – a match which is still considered to be one of the best that has ever taken place inside the steel structure – while their battles at WrestleMania XXV and WrestleMania XXVI are among the most iconic in the event’s history.
In another story from ‘That’s Gotta Be Kane!’, it was revealed by Michaels that WWE Chairman Vince McMahon never wanted HBK and ‘Taker to face each other, which explains why they did not meet one-on-one on television between 1990 and 1997.
“Prior to this storyline between The Undertaker and Shawn Michaels, there had been times over the years when people within the WWE had presented, ‘How about Shawn Michaels, the Heartbreak Kid, against The Undertaker?’ And, of course, at the time, Vince McMahon was very emphatic about, ‘Those two will never be in the ring with each other’.”
The belief at the time, according to Bruce Prichard, was that it would have been difficult for both Superstars to emerge from the rivalry with their reputations enhanced.
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