"He was such a competitor that if he lost, he would pay you pennies" - Former MLB pitcher Phil Hughes once revealed Yankees legend Derek Jeter's petty gambling habits

In June 2018, on the sports podcast "Pardon My Take," former New York Yankees pitcher Phil Hughes spoke about Hall of Famer Derek Jeter's trivial gambling habits. Hughes said Jeter occasionally enjoyed placing small bets and revealed what Jeter would do if he lost them.

Hughes and Jeter are former teammates. They played together from 2007-2013 with the New York Yankees and took home a World Series in 2009.

On "Pardon My Take," Phil Hughes said:

"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 added:

“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. He probably had to send someone to a bank and do a special request to pay you in pennies.”

"Derek Jeter a petty gambler as Yankee great would pay off clubhouse debts with pennies." - NY Daily News Sports

Jeter often had an inclination toward betting. He and George Steinbrenner had a ritual of placing one particular bet every year.

Derek Jeter placed bets annually with George Steinbrenner, the late owner and managing partner of the MLB franchise New York Yankees

Tampa Bay Rays v New York Yankees

In 2016, Jeter attended an event for the Nike Jordan Collection in Ann Arbor, Michigan, at Dick's Sporting Goods. He reminisced about when he placed bets with George Steinbrenner, the late principal owner of the New York Yankees.

Following his first summer of playing in the minor leagues, Derek Jeter attended the University of Michigan for a short period. Every year, Mr. Steinbrenner, who was an Ohio native, and Jeter placed bets on their respective football teams during the annual Michigan-Ohio State football game.

Jeter recalled the thrill and said:

"We had a lot of fun going back and forth with the rivalry.”

Jeter went on to reveal the best thing he received from George Steinbrenner after he won one of the annual bets:

“Use of his plane. Use of his plane to go to the next year’s game.”

"Derek Jeter at Hyames field at Western Michigan University, early 1990s." - @MVP Media

It is always a delight to travel back in time and become nostalgic for the good old times. It has been 22 years since George passed away and eight years since Jeter retired from MLB.