‘Use of His…’- $200 Million Worth Derek Jeter Made Sure to Travel in Style by Cashing on College Baseball Bets With Ex-Yankees Billionaire Owner

Nothing that we say about Derek Jeter can be enough. However, we can sum up Jeter’s career by saying one word: LEGEND!

Jeter made his MLB and Yankee debut in 1995. From then, he spent his entire 20-year-long MLB career with the NY Yankees. During this tenure, he appeared on 14 All-Star teams and won five Silver Slugger and Golden Glove Awards. Most importantly, the former Yankee skipper was also a five-time World Champion. The Yanks added Jeter to Monument Park in 2017 and he entered the Hall of Fame in 2020.

All things considered, Jeter was not only a fan favorite. He shared a very special rapport with the Yankee front office, including the former owner of the Yankees, George Steinbrenner.

Derek Jeter & George Steinbrenner’s annual bet

Back in 2016, Derek Jeter opened up about an annual bet he placed with George Steinbrenner. Their annual bet was during the Michigan-Ohio State Football game. Jeter was a Michigan student while George was an Ohio native and supporter. Every year, the two placed a bet on their teams.

Jeter said, “We had a lot of fun going back and forth with the rivalry.” While continuing to talk about always cashing in when he won the bet given Steinbrenner’s multi-million status, he said, “When he lost, I’d sort of lie about what I wanted.” When asked about the best thing he got from it, $200 million worth, Jeter said, “Use of his plane. Use of his plane to go to the next year’s game. We didn’t bet that, but I took it.”

READ MORE: Brian Cashman Strongly Affirms That Captaincy Should Also Be Retired With “Perfect” Captain Derek Jeter’s Jersey

This tiny example of a bet displayed great camaraderie between Jeter and his former owner. A skipper and front-office sharing common viewpoints and a good relationship will always be fruitful for the team. And such was palpable from the Yankee success.

The Yankees in 2022

The Yanks have witnessed a rollercoaster in 2022. They started the season by being the fastest team to reach 70 victories. However, after that, August happened. During the month of August, the Yanks lost six consecutive series’ and concluded the month with a record of 0.357 with 10 wins and 18 losses. This was their record in a calendar month, since September 1991. The only ray of hope through August was their superstar Aaron Judge, whose home run count did not witness a slump and, most importantly, the Subway Series victory.

For the Yankees to miss the postseason, they would have to play extremely terribly, which seems difficult given the Yankee past.

Will the Yankees be able to make a comeback this year and reach the World Series after a 13-year-long absence? Only time will tell. 

WATCH THIS STORY: New York Yankees Legend Derek Jeter Scripted The Perfect End To His Career With This Iconic Walk-off Single