Derek Jeter had a wild passion for success as a player. On that note, ‘success’ only meant a victory to him, as he would settle for nothing less. Jeter simply hated to lose, even if that meant losing a gambling bet. Former teammate Phil Hughes had some hilarious memories to share about Jeter, the gambler.

Derek Jeter is a legendary baseball icon, symbolic of the New York Yankees. He is considered one of the greatest shortstops ever, due to his magnificent record. Jeter is a 14-time All-Star player and won five World Series trophies as a Yankee. He was equally impactful in his defense and attacking skills. 

Phil Hughes made his debut as a pitcher for the Yankees in 2007. He also went on to play for the Minnesota Twins and the San Diego Padres later. Hughes is a one-time All-Star player and won the World Series with the Yankees in 2009. Interestingly, Hughes also gambled with Jeter back in the day. 

A note on Jeter’s gambling payout tactics 

Derek Jeter turned into baseball royalty while playing for the Yankees. But he wouldn’t spend his money just so easily. Even if it’s just $100, he won’t make a quick surrender. So whenever Jeter lost a gamble, he would make the winner feel his frustration.

Trending

“Going to Be a Bloodbath”: Dodgers Fans Storm Twitter After Shohei Ohtani Bobblehead Night Announcement

May 16, 2024 03:00 PM EDT

“Ronel Sweats Profusely”: Astros GM Dana Brown Comes to Blanco’s Defense Despite Refusing to Appeal 10-Game Suspension

May 16, 2024 01:00 PM EDT

Bittersweet Day for Alex Rodriguez; One Investment Pays off Hugely While the Other Is on Brink of Collapse

May 15, 2024 05:00 PM EDT

Who Is Yankees Skipper Aaron Boone’s Wife? Know More About Laura Cover

January 30, 2024 01:00 PM EST

“Don’t Foresee Them Coming Back”: Houston Astros GM Dana Brown Shuts Door On Two Injured Players’ Imminent Return

May 16, 2024 02:00 PM EDT

Get instantly notified of the hottest MLB stories via Google! Click on Follow Us and Tap the Blue Star.

Follow Us

Therefore, winning bets against Jeter was not exactly worth the fun. Phil Hughes once appeared on the ‘Pardon My Take’ podcast. He shared some flashback memories of gambling with Jeter. 

According to a report, 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.” 

Read More – “Learn to Deal With Failure, Cause It’s Coming”- Yankees Legend Derek Jeter Once Gave Advise to Young Players on How to Become Better at Game

Hughes added saying, “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.” 

The life at present for Derek Jeter and Phil Hughes

Jeter concluded his glorious baseball career in 2014. He briefly joined the ownership group of the Miami Marlins in 2017 until his resignation in 2022. Jeter now lives a peaceful family life with his wife and daughters. On the other hand, Hughes retired in 2018 and is now a memorabilia collector. 

Watch This Story – Throwback: New York Yankees Legend Derek Jeter Scripted The Perfect End To His Career With This Iconic Walk-off Single 

So, would you dare to place bets against Derek Jeter?