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Baseball, Derek Jeter, Phil Hughes

Phil Hughes shares funny story about gambling against Derek Jeter

July 26, 2018 by Steve DelVecchio • Comments
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Derek Jeter

Derek Jeter may have earned more than $265 million during his MLB career, but that does not mean the New York Yankees legend takes $100 for granted.

Like many great players before and after him, Jeter hated to lose. Apparently that passion for winning extended to friendly wagers, too. In an appearance on the “Pardon My Take” podcast this week, former Yankees pitcher Phil Hughes shared some entertaining info about how Jeter was a sore loser even when he lost a $100 bet, which to him is like losing $1 to the average person.

“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 pennies,” Hughes said, as transcribed by Jaclyn Hendricks of the New York Post.

“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. And it wasn’t like a dollar. It was a hundred bucks. It’s a lot of pennies.”

As Hughes notes, Jeter probably had to have someone go to the bank for him to make a special request for $100 in pennies, but the future Hall of Famer was willing to go to great lengths to irritate those who got the best of him.

We’ve heard some stories about Jeter over the years that are pretty tough to believe, but there’s no way Hughes would make that up. Anyone who is thinking about placing a bet against Jeter in the future should beware — winning might not be worth it.

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