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Derek Jeter reveals his one regret and talks about his historic No. 2

Regrets? Derek Jeter’s had a few (But then again, too few to mention). Yes, trace that back to Frank Sinatra’s classic tune.

While the 42-year-old wasn’t known to dwell on mistakes or make excuses during his tenure as shortstop for the Yankees, Jeter recently expressed one regret with Jack Curry in YES Network’s “Derek Jeter: Moments, Memories & Monument” program that will premiere Monday night.

“My last season, I kept a journal; every day I’d write something in there,” Jeter said. “The one regret I do have is that I wish I would’ve done that my entire career, because there are so many things that you forget. Still to this day I haven’t looked at it. It’s locked up and I haven’t looked. I’m going to be a father soon, so I’m sure one day when I sit down with my kid — or kids, if there’s multiple — I’ll get a chance to reflect and maybe brag like my dad used to do when I was younger.”

Before the Yankees take the field for a Sunday night contest against the Astros on May 14, the franchise will officially retire Jeter’s iconic No. 2 into historic Monument Park. But in 1995, when Jeter was a 20-year-old rookie, his preference wasn’t to don a single-digit uniform. Unfortunately, the Yankees weren’t accepting requests at the time, and according to Jeter, he believes his assigned number was due to an unwritten Little League law.

“You’re walking in the clubhouse, you’re scared to death, you’re nervous and you’re intimidated,” Jeter said in the interview. “The last thing I looked at was the number on my jersey. I said it time and time again: I think they gave it to me because it was the smallest uniform.

“When I was younger, I wanted to wear No. 13 because my dad wore 13. Obviously Jim Leyritz was wearing it and I think the clubhouse attendant at the time thought I wanted a different number. So going into spring training in 1997, they were going to give me No. 17, and then I said, ‘Whoa, whoa, whoa, whoa. Nah, I’m going to stick with No. 2.’ It was a good choice on my part.”

Despite the personal accolades and world championships, perhaps, in a sarcastic way, Jeter’s arrival was ill-timed. By the time No. 13 was truly available again, it was 2004, and free agent superstar Alex Rodriguez was handed it. Awkward? Probably awkward. 

But, since his annointment as captain in 2003, Jeter has been synonymous with the No. 2, and while he’s just two years removed from the game, a conversation has continued to revolve around his name. 

Sunday night will surely encapsulate his legacy in New York, but for a man like Jeter–humbled, proud and altruistic–his night will certainly push him out of his comfort zone.

“Obviously, I had a dream to play for the Yankees. Once you get there, you just want to stay there as long as possible,” Jeter told Curry. “If you do it long enough and you’re consistent, good things happen. But I still can’t imagine what it’s going to feel like having my number retired.

“I want to go in with no preconceived notions whatsoever. I don’t want to try to think about what it may feel like or what I’m going to say or what I’m going to do. I just want to go and enjoy it. A lot of times when I was playing, I never really sat back and tried to enjoy the moment. I was always thinking, ‘What’s next? What’s next? What’s next?’ Well, there’s nothing next after this, so I just want to sit back and enjoy it.”