BetMGM Derek Jeter is reflecting on his all-time favorite bet during his tenure on the New York Yankees The legendary shortstop tells PEOPLE that he once earned a trip to a Michigan Wolverines game on George Steinbrenner's private plane Jeter, who teamed up with BetMGM as the company's latest brand ambassador, stars in the company's new "legendary plays" commercial Derek Jeteris no stranger to the world of responsible gaming. During his 20-season tenure on the New York Yankees, the Hall of Fame shortstop racked up plenty of legendary plays on the field and quite a few legendary bets, as well — many of which stemmed from his love of college football, he tells PEOPLE, timed with his latest BetMGM partnership. While some left Jeterallegedlypaying off teammates in pennies ("I'm not admitting it, but it sounds like something I would do," he now jokes), his personal favorite bet secured him the ultimate game-day flex back in the day: A trip on George Steinbrenner's private plane. "I bet Mr. Steinbrenner one time, Ohio State, Michigan. And if Michigan won, I got to use his plane to go to the following year's game," Jeter, now 51, tells PEOPLE of the late Yankees owner. "And Michigan won so I got to use his plane with a group of friends, we went to the game ... We used to always go back and forth, Ohio State and Michigan, every year." "I don't even think he really remembered," he adds. "I just sort of reached out and said to someone, 'Hey, he lost the bet, so he has to give me his plane,' and the plane showed up." Never miss a story — sign up forPEOPLE's free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from celebrity news to compelling human interest stories. BetMGM Jeter's latest team-up with BetMGM sees The Captain, a five-time World Series champion, take on yet another major career role as brand ambassador. He stars in the company's latest "Legendary Plays" ad spot and will soon find himself as the face of an exclusive Jeter-themed slot game via BetMGM Casino. In the commercial, Jeter walks the field at Yankee Stadium and recalls "where it happened," as glimpses of his career highlights flash on the screen. It was a trip down memory lane, he tells PEOPLE. "It was kind of cool to see how I'm sort of in the background watching my plays, actually on the field at the same time, a couple of the plays that I made during my career," Jeter says of the ad. "So I think the finished product is pretty cool." Jeter, who says he "couldn't be prouder" of his new partnership, adds BetMGM's push for "responsible gaming" made his decision to join the team even easier. Now, he follows in the footsteps of fellow sporting greats includingBarry Sanders, Tim Howard andWayne Gretzkyas his face will appear across different promotional materials — and also online casino games featuring a current or former professional baseball player. "I come from obviously being a professional athlete and the integrity of sport is number one. That's first and foremost, but I think their focus on responsible gaming is something that stood out to me," he says. "And they've made so much progress over the years and you just watch how gaming has really increased the fan interest throughout sports." Jeter adds, "I was never really into fantasy sports, but I think the craze of fantasy sports started it because people are no longer just watching one particular game, they're watching all kinds of games. So, it's been fun to watch the evolution of betting." Read the original article onPeople