The Undertaker’s Amusing Tale of Vince McMahon Paying Off a $100 Bet in Pennies

The Undertaker put his body on the line for the enjoyment of fans and most of them always appreciated that. He is WWE’s most loyal star, as he never went to WCW despite the opportunity – for which he earned Vince McMahon’s eternal respect. That said, McMahon never failed to pull a prank on The Deadman and he recalled how McMahon once paid off a $100 bet with just pennies.

Amidst the tumultuous events of 1994, which saw Vince McMahon and his company WWE embroiled in a criminal court case over allegations of McMahon supplying illegal anabolic steroids to pro wrestlers, he never lost his sense of humor throughout the whole ordeal.

While speaking on his Six Feet Under podcast, The Undertaker recalled how Vince McMahon made a bet with him, leading to a gentleman’s agreement with a $100 stake. After losing the bet, McMahon paid off the $100 bet – but used just pennies instead as a prank.

“We made a bet, with all this going on, the trial and everything. He was a Washington Redskins [Washing Commanders] fan. I’m a Dallas Cowboys fan. We bet. Dallas beats Washington. I think we bet $100, a gentleman’s bet, $100. That joker, in the midst of all this going on, paid me my $100. You know how he paid me? In freakin’ pennies. He made someone carry a jar of pennies, $100 worth of pennies, to TV and then give it to me. He was testifying that day, which is why he wasn’t there. He paid his debt. One of his favorite things to do was to rib me. Could you imagine, with all that going on, to even have the mental capacity to think, ‘I’m going to pay him $100 in pennies.’ I’m on the road back then, like 35 days in a row, what am I going to do with a pickle jar full of pennies? That’s Vince.”

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The Undertaker and Vince McMahon have an unbreakable bond that has stood the test of time, as they continue to be loyal to each other no matter what. Regardless, The Deadman is happy for what McMahon has accomplished and that’s all that matters.

What do you make of this Vince McMahon story? Is his love for pranks one of the only good things about him? Sound off in the comments!