Vince McMahon’s Payment of a $100 Bet Made in Pennies

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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.”

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In a recent episode of his podcast, “Six Feet Under,” The Undertaker shared an interesting story about a bet he made with Vince McMahon back in 1994. At the time, McMahon was going through the steroid trial, and amidst all the chaos, the two wrestling legends decided to make a wager.

The bet was between The Undertaker, a Dallas Cowboys fan, and McMahon, a Washington Redskins (now Washington Commanders) fan. They agreed on a gentleman’s bet of $100, with the condition that if the Dallas Cowboys beat the Washington Redskins, McMahon would have to pay up.

To everyone’s surprise, the Dallas Cowboys emerged victorious, and it was time for McMahon to fulfill his end of the bargain. However, McMahon being the mischievous character he is, decided to pay The Undertaker in a rather unconventional way – with pennies.

According to The Undertaker, McMahon had someone carry a jar filled with $100 worth of pennies to the TV studio where they were filming. The jar was then handed over to The Undertaker as payment for the bet. It’s worth noting that McMahon wasn’t present at the studio because he was testifying in court that day.

The Undertaker couldn’t help but marvel at McMahon’s ability to come up with such a prank during such a tumultuous time. He mentioned how McMahon loved to play practical jokes on him, but this one took it to another level. The Deadman humorously questioned what he would do with a pickle jar full of pennies while being on the road for 35 consecutive days.

This story showcases the unique relationship between The Undertaker and Vince McMahon, filled with camaraderie and playful banter. Despite the seriousness of the steroid trial, McMahon found a way to inject some humor into their lives and lighten the mood.

It’s these behind-the-scenes anecdotes that give wrestling fans a glimpse into the personalities and dynamics within the industry. The Undertaker’s story serves as a reminder that even during challenging times, there’s always room for a little laughter and lightheartedness.

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