The Undertaker reflects on a bet he made with Vince McMahon.
The Undertaker and Vince McMahon have always had a close relationship, with Vince being the one to call on The Deadman for matches when his career was winding down. They have also known each other for almost three decades.
On the most recent Six Feet Under podcast, The Undertaker shared a story. During his infamous steroid trial, both Vince and Undertaker agreed to a bet on football. After losing the bet, Vince paid it back in full, just not in a traditional way.
“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,”
The Undertaker
Vince would end up coming out of the steroid trial with a not guilty verdict.
The Undertaker is now retired from the ring, after finishing up his career back at WrestleMania 36 when he faced AJ Styles in a Boneyard match.
H/T to Fightful for transcription
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