Derek Jeter is among one of the biggest names to come out of Major League Baseball. His contribution to the sport, especially to the New York Yankees franchise, is unquestionable. A five-time World Series champion, Jeter was one of the few players to spend his entire career with one team. Out of the twenty years he played in the Bronx, the former shortstop was team Captain for eleven of them. The Yankees were once Jeter’s dream team, but at one point in time, the Pinstripes left him feeling disappointed.

It’s a well-known fact that employers and employees don’t always have the best relationship. Both sides need to have equal respect for each other to make things work. But at the end of the 2000s decade, Jeter felt dissatisfied with his team. In fact, manager Brian Cashman gave him a biting reminder when the ex-shortstop became a free agent for the first time in his career.

Derek Jeter lost his trust in general manager Brian Cashman after a time

2009 was a good year for the Bronx Bombers as they finally won a World Series after a nine-year drought. It was also one of the best seasons of Jeter’s performance. But he seems lost that talent in 2010, just as his contract with the Yankees was about to end. Given that display, the Captain’s future with the team was unclear. And among contract extension discussions, Cashman clearly told Jeter to look at other teams if his current offer made him dissatisfied.

It was something that essentially shocked the Yankee player, who had not expected it of Cashman. Speaking about that experience in his docuseries, The Captain, Jeter said, “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.”

READ MORE – “All I Know Is I Made the Last Offer” – Yankees Legend Derek Jeter Once Had Conflicts With GM Brian Cashman About the Disagreements Over Contracts

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Players may play a sport out of passion, but the financial part comes as an unfortunate side effect sometimes. The Hall of Famer continued, “Now I didn’t wanna have many conversations with Cash; I didn’t. Didn’t really wanna speak to him because I’d lost that trust. Never said anything bad about him, but I didn’t wanna see him.” 

The New York Yankees would probably have been at a loss if Jeter had left

The writing was on the wall, as they say. The former shortstop was disappointed when these negotiations became public knowledge. Always one to keep personal things private, the Captain didn’t like it when the matter became public knowledge. Yet, he persisted.

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Playing in Pinstripes had been a dream for the kid from Kalamazoo, and this other side of the sport wasn’t going to deter him. It’s highly unlikely that the front office would have traded Jeter or that he chose a different team. But had it happened, not only would it have left fans devastated, it would have changed the course of Yankee history.