When you think of Derek Jeter, you think of clutch moments, World Series titles, and the poise of a captain who led the Yankees to five championships. A Hall of Famer, a leader, and a legend, Jeter was the ultimate competitor under the bright lights of October baseball. But there’s a side of The Captain that even die-hard fans might not know.

Beneath the calm exterior was a man who thrived not just on the field, but also when the stakes were high off it. A quiet gambler, not in the casinos, but in locker room showdowns over college football. Yes, Jeter was known among teammates and friends as someone who loved to bet on college games. And not just bet, but to win.

Well, it’s a lesser-known chapter in the story of one of baseball’s greatest icons, recently revealed by the man himself. As it turns out, Jeter’s sharp instincts weren’t confined to the diamond. One of his legendary locker room bets earned him what many considered the ultimate flex during his playing days. We bet even the biggest fan of Jeter doesn’t know this story!

“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 revealed to PEOPLE about 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.”

The Yankees’ yesteryear owner, George Steinbrenner, was one of the most powerful and image-conscious owners in MLB history. His private jet wasn’t just transportation, but was a symbol of status and influence. So the idea that Derek Jeter won access to Steinbrenner’s jet, and that Mr. Steinbrenner honored it, speaks volumes about both of them. And for Jeter, it underscores his legendary competitiveness, charm, and ability to win in more ways than one.

Now, all these are coming up just when Jeter is starting his next chapter.

Derek Jeter’s latest move has him teaming up with BetMGM, stepping into a new role as a brand ambassador. The 5x World Series champ is currently promoting the fantasy game, and pretty soon, he’ll even have his own Jeter-themed slot game on BetMGM Casino.

Derek Jeter 2.0 in the making?

Wait, before you conclude. We are not talking about whether any new player will become Jeter, but the next generation. While talking about his children, Jeter shared how his daughters are moving towards tennis, soccer, and swimming. However, it is his youngest kid, Kaius, who likes to swing.

We are not claiming that Kaius, who is just 2, would become the next Jeter. But we can definitely count on Jeter’s mentorship skills.

As part-owner and CEO of the Marlins from 2017 to 2022, Jeter shifted his focus to shaping an entire organization. He instilled a culture of accountability, professionalism, and preparation, values he lived by as a player. He also worked with young executives, coaches, and prospects, setting high expectations and reinforcing a team-first mindset.

Jeter is more of a player personality and quite successful as a mentor. And for his youngest kid, what could have been better than getting someone like Derek Jeter at home!

“My son walks around, everything in his hands, he’s swinging it, trying to hit someone,” Jeter shared.

Now, only time will tell if his son continues to swing and starts to love the diamond. Then, if not the next Jeter, we can expect the next Robinson Cano.

For reference, Jeter took Cano under his wing during his early years with the Yankees. Cano benefited from Jeter’s example of discipline, preparation, and professionalism. He helped Cano evolve into an elite second baseman.

So, let’s wait and watch what’s coming next.