For two decades, Derek Jeter was the gold standard of baseball professionalism, a player even his rivals had to respect. But a recent business deal has one of those former rivals questioning the very integrity he once admired.

Almost a year into the legendary partnership between Derek Jeter and BetMGM, former Red Sox player Jeff Frye is not happy.

“I’ve got to admit this broke my heart a little… played most of my career against Derek Jeter… I always admired him… I have been asked to partner with Gambling Entities… my integrity doesn’t have a price,” the ex-Red Sox second baseman posted on X.

Derek Jeter joined the BetMGM group in July 2025 as a brand ambassador under a multi-year deal. He led the “Legendary Plays” campaign filmed across Yankee Stadium. But BetMGM went further with its promotion.

The commercial showed Jeter walking through Yankee Stadium, watching key moments from his own highlights. The ad mixed real stadium visuals with digital recreations of famous Yankee Stadium plays.

BetMGM used this to connect with baseball fans’ memories by making an interactive betting entertainment platform. Jeter also became part of a wider ambassador group, including Wayne Gretzky and Barry Sanders.

He said the goal was to make fan engagement stronger through modern sports platforms.

“It brings a lot of excitement to the fan base.”

The platform has included a ‘Derek Jeter slot game,’ a first-of-its-kind online casino game.

Jeter also noted that betting used to feel hidden but is now openly discussed. He admitted to gambling rarely and joked about sticking to five-dollar blackjack tables. He added that fantasy sports helped shift betting into regular sports conversations. BetMGM said the deal focuses on the US and Canada markets with messages about responsible gambling.

But at the same time, players across MLB have raised concerns about rising online abuse due to gambling.

Liam Hendriks reported receiving death threats tied to losing bets, affecting the player mentally. Brewers’ star Christian Yelich revealed, “Receiving hostile messages from bettors is a nightly thing.”

Former Met Brandon Nimmo said, “Gambling on baseball is a clear-cut line,” stressing strict separation.

Jeff Frye has publicly warned that gambling pressure changes how fans treat players. This has also brought the integrity of the game into question. But with the BetMGM campaign, Jeter has vouched to help promote responsible gaming.

Concerns have grown after cases like Tucupita Marcano receiving a lifetime MLB ban.

It was reported that he placed around 387 baseball-related bets, including 25 bets on the Pittsburgh Pirates, while on the roster.

NBA’s Jontay Porter also received a lifetime ban for betting-related violations in 2024.

Not sure what the future holds for gambling in baseball, but let’s look at the history.

Beyond Derek Jeter: The history of gambling and baseball

In the late 1800s, gambling appeared in baseball games with literally no oversight. Bookmakers often influenced outcomes, with players sometimes receiving small payments for fixed plays.

MLB recorded multiple suspicious games during the 1900s, making this a nationwide concern. Reports from 1905 and 1908 show gambling cases across several major league cities, including Chicago. And this set the stage for the 1919 World Series controversy involving White Sox team.

The 1919 World Series featured the Chicago White Sox and the Cincinnati Reds. The White Sox lost 5-3 against the Reds. During that time, eight White Sox players were accused of accepting money to lose the series.

Investigations in 1920 revealed confessions linking gamblers to team misconduct. Commissioner Kenesaw Landis banned eight players permanently. Public outrage forced MLB leadership to enforce stricter rules on gambling.

MLB created the commissioner role in 1920 to restore trust after the 1919 scandal. Judge Landis suspended players and enforced lifetime bans to protect game integrity.

During the 1930s and the 1950s, illegal betting networks spread quietly around baseball cities.

Players faced strict warnings after FBI reports linked gambling groups to stadiums. This era set the foundation for strict punishment rules that later shaped the Pete Rose case.

The 1989 investigation found Pete Rose betting on the Cincinnati Reds while managing the team. The MLB Dowd Report documented over 50 betting instances involving the Reds. Commissioner Bart Giamatti issued a lifetime ban on Rose.

In 2018, the Supreme Court ruling in Murphy v. NCAA struck down PASPA, the landmark nationwide betting law. Legal betting expansion pushed MLB toward partnerships while keeping strict player restrictions across the league.

After the 2018 ruling, MLB signed deals with DraftKings and FanDuel sportsbooks as part of their expansion. Teams integrated betting data into broadcasts, increasing fan engagement during live games.

Despite growth, MLB bans players and staff from betting on baseball games, showing strict enforcement of rules. Fans now experience live odds during games, and have shown changes in their viewing habits. Reportedly, fans bet on games when live odds are shown on screen or are being talked about.

Gambling history has reshaped MLB. From scandal risks to regulated entertainment, the relationship between gambling and the league is just starting.