Undertaker Explains Vince McMahon's Decision to Pass on Dream Match with Sting

Pro wrestling fans have got to see a lot of dream matches over the years. Sadly, they can't all happen, and that included Sting vs The Undertaker. Although there was a window of time when the match could have seen the light of day, Vince McMahon simply never booked it.

The Undertaker explained that the match between him and Sting never happened due to Vince McMahon not seeing it as a fit for WWE, despite fan anticipation. By the time Sting arrived, Calaway felt he was nearing the end of his career, and the timing didn't align for the matchup.
Why Sting vs The Undertaker Never Happened

During his Six Feet Under podcast, The Undertaker opened up a bit about why that legendary dream match against Sting didn't happen. It seems that it was all Vince McMahon's call, and he never went that direction.

In discussing why he never faced Sting, Mark Calaway mentioned that the opportunity simply didn't materialize. Despite the anticipation from fans and artwork depicting the potential matchup, Vince McMahon didn't see it as a fit for WWE, and Calaway felt it wouldn't live up to the high expectations. He noted that by the time Sting arrived, he was already nearing the end of his career, and the timing didn't align for the match to happen.

"It just didn't work out. He had a short run in WWE and Vince didn't want it. For whatever reason, I don't know what it was. He didn't feel it. Everybody else was clamoring for this match for quite a few years. A year or two into that character change, I mean, people were already sending me artwork with the billboard or the poster. It just never worked out. The match would have been good, but I don't think it would have lived up to the expectations that people have for it. People always think about things in a certain sense. I think they thought in their mind of Undertaker, 2007 or 2008 versus Sting. It was later on than that. I can say I was way on the backside of what I was going to do when he got there.”

The Undertaker recently commented on how Sting retiring from in-ring competition "ruined" the idea of him coming back. It seems that a match against the Stinger is the only thing that could get The Phenom to wrestle again.

Only time will tell if Sting and The Undertaker ever share the ring for any reason. It would take a lot, but odds are we are years past the idea of that match ever going down for real.