Sting vs. The Undertaker: Vince McMahon "Didn't Want" Dream Match

One of professional wrestling's biggest "what if" scenarios has been cemented as a hypothetical. Sting retired from the squared circle at AEW Revolution, capping off a multi-decade career as champion alongside tag partner Darby Allin. The Icon's exit from the wrestling business came four years after his WWE foil, The Undertaker, called it a career. The Deadman also retired on top, besting AJ Styles at WWE WrestleMania 36 before riding off into the sunset. Given the nature of their gimmicks, Sting and The Undertaker were linked for just about their entire careers despite never truly crossing paths on screen.

That said, there was one single opportunity to run Sting vs. Taker. After holding out for 12 years, Sting made his long-awaited WWE debut in November 2014, setting himself on a collision course with Triple H for that following March's WWE WrestleMania 31. Taker would face Bray Wyatt at that show, marking the first and only time both men competed on the same pay-per-view card. Five months later, Sting would get injured in a match against Seth Rollins and be forced to retire. He would come out of retirement to wrestle for AEW in 2021, six months after The Undertaker wrapped up his career. If company boundaries weren't enough, this effectively closed the small window the professional wrestling industry had to have these two face off.

Vince McMahon Passed On Sting vs. The Undertaker

Vince McMahon "didn't want" Sting vs. The Undertaker.

Speaking on Six Feet Under, The Undertaker shared kind words to Sting following his retirement at AEW Revolution. This inevitably led to the age-old question about why Sting vs. Taker never took place.

"[Sting] had a short run in WWE and Vince didn't want it for whatever reason," Taker said. "I don't know what it was. He just didn't feel it. Everybody else was like, people have clamoring for this match for quite a few years. A year or two into his turn or that character change (when Sting ditched the surfer gimmick for The Crow-inspired look), people were sending me artwork with the billboard of the poster. It just never worked out."

While Taker is optimistic about the bout's quality, he cast doubt on it attaining that "dream match" threshold that fans had theorized for years.

"The match would have been good. But I don't think it would have lived up to the expectations that people have for it," Taker continued. "People always think about things in a certain sense. I think they thought in their mind of Undertaker 2007-2008 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."