During the latest episode of his Six Feet Under podcast (via Fightful), The Undertaker spoke about a time he made a $100 bet with Vince McMahon and the WWE founder paid him back in pennies. The incident happened in 1994 when McMahon and WWE were in the middle of a court battle over accusations of giving illegal steroids to wrestlers.
He said: “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.”
He said: “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.”
