The bond between The Undertaker and Vince McMahon was well established during the legend’s iconic in-ring career.
For 30 incredible years between 1990 and 2020, Mark Calaway donned the black hat and coat and performed at the highest level in WWE.
Debuting at Survivor Series at the onset of the nineties, he was WWE Champion inside a year and soon became a trusted hand to McMahon and an absolute locker room leader in his own right.
The wrestler has made no secret of his respect for what McMahon did for his career during their tenure together in the WWE, even going along with controversial storylines and the call to end his iconic WrestleMania undefeated streak at the hands Brock Lesnar.
If their mutual respect was undoubted at the climax of ‘Taker’s career, it’s fair to say that it wasn’t without a few hairy moments earlier on – one incident in particular seeing the Deadman catch McMahon’s full wrath backstage.
Back at WrestleMania 8 in 1992, with Undertaker still just a couple of years deep into his WWE run, he was paired with grizzled veteran Jake ‘The Snake’ Roberts.
Roberts was on his way out of WWE at the time and, to captialise on Undertaker’s own rise through the ranks and recently found fan popularity, McMahon had ordered ‘Taker to win, and decisively so.
Disgruntled Roberts, however, was well aware of the boost his opponent’s stock would get at his expense by taking a Tombstone and a pin cleanly in the middle of the ring, and very much had different ideas.
Already unimpressed by plans for Undertaker to survive several attempts of his own finisher, the DDT, Roberts took matters into his own hands, as the pair discussed recently on the Six Feet Under podcast.
Taker explained: “We had the finish: hit Jake with the [Tombstone], one, two, three. That’s where we’d left it, and we knew what we wanted to do [but] a lot of s*** is ad-libbed.
“It wasn’t like we were stuck together all day, locked in conversation. We had the finish. We got out there, and old slippery here said: ‘Give me that Tombstone on the floor.’
“I [thought]: ‘Really? We didn’t talk about that, is that part of the finish?’ So I gave him one or two Tombstones on the floor before I throw him back in… then I’m getting all my pomp and circumstance after the match and Jake gets out of the building.”
If Roberts fled the proverbial scene of the crime because he knew what was coming, an inexperienced Undertaker – or green, in wrestling parlance – did not.
He went on to detail McMahon’s reaction: “I’m thinking: ‘Ah, that was pretty cool… that was pretty vicious.’ I come [backstage] and the old man’s waiting on me.
“[He said]: ‘What the hell was that?… why in the hell would you Tombstone him on the floor? Nobody could see it!’
“He just eviscerated me. The veins are all in his head and then it dawned on me. I was like: ‘That son of a b***!’ He got me.
A cackling Roberts reiterated that his chicanery wasn’t intended to hurt ‘Taker, saying: “It was nothing towards you,” to which the seven-footer replied: “I knew that but, believe me, I’m the one that got the heat!
“It was a life lesson, and it was something I always remembered. From that point, I double checked finishes and always checked with the old man we were on the same page.
“But he got me. I was p***** that night.”
Undertaker has remained a sizable presence in WWE since his 2020 retirement, even appearing at the most recent instalment in 2024.
He turned up at the climax of WrestleMania XL and aided Cody Rhodes in winning the Undisputed title from Roman Reigns.
