Derek Jeter’s Petty Gambling: A Playful Stunt Or Reason For MLB Concern?

Written By FairwayJay on July 27, 2018
Derek Jeter

Public perception was always important to Derek Jeter while he played for the New York Yankees. Jeter’s perception will reach the ultimate height in 2020 when he becomes a first-ballot inductee into the National Baseball Hall of Fame.

Jeter was a superstar shortstop and an icon beloved in New York, where fans are especially tough on players. Jeter is now the CEO and part owner of the Miami Marlins and has his 12,000-plus square-foot castle-like compound on the market for more than $14 million in Upstate New York.

He’s got money to burn, and apparently he had pennies to provide during his time with the Yanks.

Paying off in pennies

Former Yankees teammate Phil Hughes, who was traded by the Twins to the Padres this season, joined the “Pardon My Take” podcast this week and had a few comments about Jeter and his unusual payment method on paying off sports bets. Hughes won a World Series with the Yankees and Jeter in 2009, and he still has “really good” memories of playing for the Yankees.

Hughes said Jeter and some of his teammates would bet “a few bucks” on various things like football games. When he lost a bet, he would pay off his debt in pennies. And, according to Hughes, bags and bags of pennies up to $100.

“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 recalled.

“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.”

It doesn’t appear ‘Jeet’ was a cheat, but paying off bets in pennies is a little petty and peculiar.

Legal betting and acceptance of sports betting

There’s no evidence of foul play here, and it’s widely known that pro athletes like to do some gambling on the side during their down time.

However, what if that “something stupid like a college football game or something” was periodically an MLB game? Would Major League Baseball and the commissioner’s office look at this type of supposed innocent behavior a little differently?

Betting like this leads to other forms of sports betting, doesn’t it? Isn’t that how most bettors start out?

Since Major League Baseball is becoming more accepting of sports betting and trying implement safeguards while also attempting to get in on the action and profits themselves, how should the league react to this type of story? We know how they reacted to Pete Rose’s wagering habits and betting on baseball, and certainly, there are other stories like this that has surrounded baseball clubhouses and players.

Does the perception change knowing that baseball’s golden boy and soon to be Hall of Famer Derek Jeter was betting on games?

Now that sports betting is legal in the U.S. following the Supreme Court decision to strike down the federal ban (PASPA), the perception has certainly changed despite the action having been going on for decades.

If a college coach football can be fired from his position for participating in an NCAA basketball tournament pool like Rick Neuheisel was in 2003 at the University of Washington, should other sports and pro leagues be more concerned as they continue to implement, modify and educate on sports gambling?

FairwayJay Avatar
Written by

FairwayJay is a leading national sports and gaming analyst and is recognized as one of the sports industry's most insightful professionals. Jay has pursued his passions and maintained a pulse on the sports, gaming and poker industries while living in Las Vegas for nearly two decades. He's been a regular featured guest on sports and gaming radio shows, podcasts and produces sports betting and related industry articles and content for various sites and sources.

View all posts by FairwayJay