In the 121-year history of the Yankees, few players have surpassed Derek Jeter’s impact and association with the club. However, to think that the relationship between the Hall of Famer and the Bronx Bombers was always smooth would be a mistake.

In late 2010, Jeter’s 10-year, $10 million deal with the Yankees was set to expire. Less than two years prior, Jeter had played an instrumental role in helping his club win their fifth World Series with him. According to sources, the then-36-year-old was told to ‘shop around’ if he was not content with the Yankees’ initial three-year, $45 million offer.

Derek Jeter took umbrage with GM Brian Cashman’s strategy and claimed that it sought to portray him as greedy.

Jeter told the media:

“I was angry about it because I was the one who said, ‘I didn’t want to do it, I was the one who said, ‘I wasn’t going to do it.’ To hear the organization tell me to go shop it, when I just told you I wasn’t going to, yeah, if I’m going to be honest, I was angry about it.”

On Dec. 7, 2010, Jeter and the New York Yankees agreed on a three-year, $51 million deal that would keep the shortstop around until the end of 2013. Despite the fact that a resolution was reached, Jeter made no bones about his dissatisfaction, and would go on to state at the press conference to announce the new deal:

“I’d be lying if I said I wasn’t angry how some of this went.”

Jeter signed a one-year extension for 2014, and played the final game of his MLB career against the Boston Red Sox on Sept. 28. While Jeter’s relationship with Yankees management was largely devoid of conflict, the 2010 contract negotiations represented a nadir in that relationship.

2010 contract talks frayed relationship between Cashman and Derek Jeter

Although the relationship between Derek Jeter and Cashman fell out of the limelight after the final deal was reached, the sentiments remained. In his 2023 docuseries The Captain, Jeter opened up about how the talks hurt his trust in GM Cashman:

“It changed my feelings on the front office. I knew now – you’re able to just throw me out. You’re able to not treat me with the respect that I’ve shown you throughout my entire career. It’s not a two-way street. It was a reminder that it’s a business.”

In an age of record-setting deals, don’t be surprised if similar storylines play out around MLB in the coming seasons.