Hall of Famer Derek Jeter has seen many wins throughout his twenty years wearing the Pinstripes. But those wins did not come without any losses. The former shortstop has had quite a few disappointing moments in his career as well. Captain Clutch, over the years, has told the upcoming generations multiple times that failure is inevitable. And that it is coming no matter what, so to be successful, they should be prepared for it.

During his recent catch-up with the NFL legend Eli Manning, Jeter opened up about the most disappointing moment of his career.

When the former shortstop finally was asked about the dissatisfactions of his career, not one but he revealed two such moments that hurt him the most to date.

What did Derek Jeter say about the disappointments of his career?

The baseball Hall of Famer recently sat down with NFL Hall of Famer Eli Manning on his show. Therein, they talked about many things. One of the things that Manning asked Jeter was about the disappointments he had to face in his career. 

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The first thing that Jeter said was, “We lost 2001 world series. we were so close, so that hurts.” The second disappointment for Jeter came when the Bombers lost to their fiercest rival in ALCS. “We blew a 3-0 lead against Boston,” said Jeter of losing to the Boston Red Sox in 2004.

There was also a time when Jeter was about to get transferred back to the minor league. But he did not count that as the disappointment of his career. Notably, even though he was incredibly successful in the ballparks, Jeter’s disappointment is proof that no one can achieve everything in sports.

What else did Jeter talk about with the NFL star?

On his show, Manning asked Jeter if there was one World Series of his that was better than the rest of them. But Jeter’s reply to that question would leave any Yankee or Jeter fan in awe of him. 

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He simply said choosing a favorite World Series is similar to choosing a favorite kid among the others. He went on to say that every win had its importance. And that he won’t be able to choose any one of them. By the way, which is your favorite World Series win for the Yankees? Leave your comments below!