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During the Steroid Trial, Vince lost a $100 bet to The Undertaker over a Cowboys vs Redskins game. Vince paid Taker $100 in pennies.
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Quote from Taker:

"I was with him (Vince) through the trial back in the day ... funny story about that. He had all that going on, he had the body building, the trial, and all that is just going to hell. So he was ... at the time...he's a big Redskins fan, right? And I'm a big Dallas Cowboys fan, right? Even with all that going on, we made a bet ... because Dallas plays Washington twice a year...anyways, so we just made a casual, you know, $100 bet over who was going to win the game. As usual, Cowboys win and he was in the middle of going back and forth in the trial...He sent somebody to TV - he wasn't gunna be there - he sent somebody with a hundred dollars in pennies to pay me off. I mean, you know, with his whole world caving in on him...his entire day could be going completely to shit and you ask him how his day is... it's fucking great."

Source: The Bill Simons Podcast (1 hr 26 minute mark)

https://podcasts.google.com/?feed=aHR0cHM6Ly9yc3MuYXJ0MTkuY29tL3RoZS1iaWxsLXNpbW1vbnMtcG9kY2FzdA&ep=14&episode=Z2lkOi8vYXJ0MTktZXBpc29kZS1sb2NhdG9yL1YwL0tkTkh5djhmYzEzdklVMm5HeDVXeTVqWmRTVTBhNXlHTE5FSWt0MHJtTzA

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4 years ago