How The Undertaker Changed Vince McMahon's Booking for WrestleMania 25

The Undertaker vs. Shawn Michaels at WrestleMania 25 is regarded as not only a career highlight for both men, but as one of the greatest professional wrestling matches of all time. The bout lasted just over 30 minutes and was third-from-last on the show (something that would be resolved with their rematch a year later), but Vince McMahon apparently had a much smaller vision for the match originally. Former WWE referee Marty Elias explained on the Chat, Grapple and Cheap Pops Podcast recently that McMahon had the match slotted for third on the card, ahead of the "Miss WrestleMania" battle royal, and was only allotted 15 minutes. 

Elias explained how Undertaker changed that (h/t Sportskeeda) — "We're sitting there and 'Taker looks at Shawn and he goes, 'Shawn, how long you been with this company?' Shawn goes, 'Most of my life.' And he goes, 'Hmm, 15 minutes? Third? That ain't gonna fly.' Michael Hayes [responds], 'Oh, hey, hey, I'm gonna go talk to Vince. Don't worry, we'll see if we can get it changed.'"

Michaels retired a year later following his rematch with Undertaker, while "The Deadman" wouldn't hang up his boots until after his cinematic "Boneyard Match" with AJ Styles at WrestleMania 36. During The Last Ride documentary, Undertaker admitted he was jealous of Michaels being able to step away so easily while he chased his retirement match for years. 

"I'm so envious of Shawn because he was able to walk away and be...he was good with it. Do I wish I had that kind of clarity? Absolutely," Undertaker said. "He had the clarity before going into the match. Hopefully, when I have the match I'm looking for, I have that clarity. 'Okay, that's it.'"

The pair's WrestleMania matches centered around Undertaker's undefeated streak, which wouldn't end for another four years until "The Phenom" faced Brock Lesnar. 

"Internally, and the way this business works, I knew that someday it probably would [end]," he told Ariel Helwani in 2020. "In our industry, you don't walk away like Floyd (Mayweather) and retire undefeated, like Rocky Marciano. It just doesn't happen that way in wrestling. It was always in the back of my mind that it would end. Although most of my peers and people I work with thought it was a horrible decision. And I just asked Vince [McMahon] 'Are you sure? Is this what you want.' He was like 'If it's not Brock, who could beat you?' From the way the streak was built and by that time obviously [nobody could]."