BRONX, NY – SEPTEMBER 09: Derek Jeter #2 of the New York Yankees is introduced during the 75th New York Yankees Old Timers Day on September 9, 2023 at Yankee Stadium in the Bronx, New York. (Photo by Rich Graessle/Icon Sportswire via Getty Images)
Icon Sportswire via Getty Images
The New York Yankees have almost always been willing to spend aggressively when a superstar becomes available, particularly when the move could meaningfully improve their chances of winning a World Series.
That philosophy has involved some of the biggest contracts in baseball history, including several deals on the current payroll.
“The Yankees are perennially one of the highest-spending teams in MLB,” Brendan Kuty wrote for The Athletic. “When the club re-signed Aaron Judge to a $360 million deal in 2022, he became the highest-paid position player on an average annual basis at the time. Gerrit Cole’s $324 million deal with the Yankees in 2019 was the richest contract ever given to a starting pitcher at the time.”
But one of the franchise’s other major ongoing contracts is now headed toward a very underwhelming conclusion. And the team can thank a former icon for the burden.
New York Yankees Legend Derek Jeter Owed ‘Debt Of Gratitude’ After Fleecing Old Team With $265 Million Contract Burden
After then-CEO of the Miami Marlins and former Yankees captain Derek Jeter traded Giancarlo Stanton to the Yankees in 2017, the reigning National League MVP slugger arrived in the Bronx with considerable expectations.
The Yankees acquired him in a blockbuster deal that included some cash considerations from the Marlins, but New York still assumed roughly $265 million of the remaining money on Stanton’s contract, making the move an enormous financial commitment.
At first, Stanton quickly demonstrated why New York made the investment, but since then, injuries have repeatedly interrupted his availability.
“The Marlins owe a debt of gratitude to Derek Jeter, who traded Giancarlo Stanton from the Marlins to the Yankees in December 2017, saving the franchise $265 million,” Bob Nightenale recently noted for USA Today. “Stanton played in 158 games his first year with the Yankees, hitting 38 homers with 100 RBI, but will have missed 588 games in the past eight seasons once this year ends.”
Stanton ongoing season appears all but lost after he suffered his latest injury setback and the Yankees seem likely to move on from him despite the fact that he is still owed $15 million with a significant buyout on the contract they inherited from Jeter.
New York Yankees’ $265 Million Bet Comes Full Circle After Derek Jeter Move
The timing is particularly notable because Stanton entered New York as one of baseball’s most accomplished hitters. He was the reigning National League MVP and had just produced one of the greatest power seasons in recent MLB history.
Yet the Yankees ultimately received far less sustained production than they hoped for from the blockbuster acquisition and they are expected to cut their losses despite the remaining financial burden.
“I expect Stanton to be released after the season,” NJ.com’s Randy Miller wrote. “I was hoping to see him hit his 500th career homer in a Yankees uniform, but I don’t know if he’ll get there with anyone now. He’ll be 37 in November and is still 44 away.”
That would leave the Yankees facing an uncomfortable reality: a move once designed to supercharge a championship contender could end with the club cutting ties with the player it acquired for a massive financial commitment.
Derek Jeter’s Marlins, meanwhile, accomplished precisely what they wanted from the trade — escaping most of Stanton’s contract and gaining financial flexibility during a rebuild. Though he is no longer in the Marlins’ front office, Jeter can now look back on that decision and claim he got the better of his old team.

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