• According to Phil Hughes, Derek Jeter was the pettiest gambler.
  • Jeter would go as far as paying off his bets with pennies. "But it wasn't a dollar," says Hughes. "It was a hundred bucks."

Former Yankees hurler Phil Hughes joined Pardon My Take on Wednesday and shared some insight into Derek Jeter’s gambling habits. Per Hughes, Jeter was the pettiest gambler — often paying off $100 college football bets with pennies.

The reason? His burning hatred of losing, which I can actually respect.

The full quote:

“He had this thing. He liked to do small little wagers every now and then. But he was such a competitor that if he lost, he would pay you in pennies. So it would be like a hundred bucks on something stupid like a college football game that’s going on or something and if he lost, he would literally have a bag of pennies the next day. But it wasn’t a dollar. It was a hundred bucks. It’s a lot of pennies. He probably had to send someone to a bank and do a special request to pay you in pennies.”

We all have friends who never pay their bets on time and those who will always want to go double-or-nothing until they get even. And then there are the petty friends, who just have to throw a wrench in when paying — as a way to almost get the last word in.

Winning while losing, if you will.

I have a friend like that. After winning a $200 bet we made recently in Las Vegas, he ripped two $100 bills in half and gave me the larger half of each, pocketing the smaller halves with a wry smile.


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Now, for those who don’t know — the larger half is legal tender. It’s useful to know that if you ever accidentally rip a $20 or get paid from a petty friend. However, a lot of places won’t take 51% of a $100 bill — and let me tell you how dumb I felt trying. (Again, my friend sort of won while losing.)

I eventually went to the casino cashier, which I figured would replace my ripped $100 bills. Well, the first lady I spoke to said she couldn’t help me, but the manager overheard my request and gave me two crisp $100 bills.

I actually can’t wait to lose a bet to him in the future to get my Jeter-esque payback.

The lesson? Don’t be a Jeter unless someone “Jeters” you first.

Credit:

Jasen Vinlove-USA TODAY Sports. Pictured: Derek Jeter

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