On the most recent episode of his “Six Feet Under” podcast, The Undertaker discussed an occasion where he wagered $100 with Vince McMahon and received his payment in pennies.
This happened in 1994 when McMahon was going through the steroid trial.
The Deadman said, “We made a bet, with all this going on, the trial and everything. He was a Washington Redskins [Washington 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.”
