5 Backstage stories we learned about The Undertaker & Kane on WWE Untold

#3 Vince McMahon did not want The Undertaker vs. Shawn Michaels

From The Rock vs. Hulk Hogan to John Cena vs. The Undertaker, every dream match that WWE fans have seen over the last few decades has ultimately been approved by Vince McMahon.

Between 1990 and 1997, McMahon had the opportunity to book a dream encounter between The Undertaker and Shawn Michaels. However, although the two men often competed as tag team partners and opponents in dark matches and at live events, their first one-on-one match on television did not take place until September 1997 at In Your House: Ground Zero.

Why? Well, according to WWE Producer Bruce Prichard, both characters were so strong in that era and it was difficult to book a storyline where either of them could lose and emerge with their reputation enhanced.

Michaels elaborated on this by confirming that it was McMahon who never wanted to see him face The Undertaker.

“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’.”