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Derek Jeter Reveals One Of The Biggest Regrets Of His Career To President Obama

And it's not what you'd expect.

Derek Jeter's 20-year career as a New York Yankee is his greatest achievement to date. By his 40th birthday two years ago, the Yankees' captain had racked up five World Series titles, 14 All-Star Game appearances and a lifetime of memories.

But that's not to say he doesn't have some regrets about his career. Most of all, he wishes that he could have shared those experiences with the children he still hopes to have someday with his fiancée, Hannah Davis.

Jeter revealed as much in a conversation with President Barack Obama, which was published Wednesday on Jeter's media outlet, The Players' Tribune. In fact, Jeter actually kept a diary during his last season in 2014. He said he would jot down what he was thinking and feeling after each game on his retirement tour to create a "Dad scrapbook," as he called it. 

Jeter and Obama had a conversation on mentors, role models, family and more.
Jeter and Obama had a conversation on mentors, role models, family and more.

Before Jeter could explain further, Obama jumped in: "[You started the book to show] that Dad actually had some game." Despite a Hall-of-Fame career, Jeter has a hard time grappling with the idea that his kids will grow up only understanding their dad's career through history and highlights, never realizing or feeling the impact Jeter had in the moment. 

"I wish I would've done that [kept a diary] throughout my career. There are so many experiences that you tend to forget," Jeter continued. "So if I could go back to 25, I would say, [write in a diary] every day." 

Luckily for Jeter, at 41, he still has plenty of time to mold another lifetime of memories, but this time, with his future wife and children.

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