On May 29, 1995, the baseball world was treated to their first sighting of Derek Jeter playing in a Major League Baseball Game. A highly touted prospect, Jeter wore jersey number two because it was one of the few numbers available in his size. After a rather disappointing performance, the front office decided to send the shortstop back to Triple-A. Still, there was someone who believed in his talent. Next season, newly appointed Yankees manager Joe Torre brought Jeter back. After all, he was the 6th best prospect in the sport according to Baseball America.

Team owner George Steinbrenner remained unconvinced of his ability to play in the major leagues just yet, but he gave him a chance. By the end of the 1996 season, Jeter exceeded all expectations. He won AL Rookie of the Year in a unanimous sweep and what followed was nothing short of a legendary career. The ex-shortstop became not just the face of the Pinstripes, but also of baseball itself. As if in a flash, the year 2014 arrived, and Jeter declared his intentions to retire.

Derek Jeter felt like he could still play when he announced his retirement

To say that Bronx fans were disappointed to lose their captain would be an understatement. The shortstop that led his team to five World Series championships would no longer wear pinstripes. Time had caught up with him, and the kid from Kalamazoo had fulfilled his dream of playing baseball.

The cycle of injuries and rehab was certainly getting tiring and Jeter felt that 2014 was the year. “I still feel as though I could play. I just don’t want to. I want to call it a career,” he told The New York Times. Quit while you’re ahead, the saying goes. It’s exactly what Jeter did. Interestingly, the Hall of Famer once revealed another reason why he decided to hang up his uniform.

Jeter felt forced out by the New York Yankees at the time

Over the years, many media outlets have tried to get an insight into the former ballplayer’s mind. But it was ESPN’s docuseries, The Captain, where the tight-lipped Jeter finally bared all. While discussing his performance in the 2010 season, he revealed that GM Brian Cashman gave him a brutal reminder that MLB was a business at the end of the day.

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And 2014 was a repeated reminder. Injuries and his age, of course, played a part in his decision and it was ultimately Jeter that said the words. But at the time at least, he felt that the Yankees were forcing him out. But in the years that have followed, Jeter seems to maintain a good relationship with the front office still.

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