Derek Jeter asked President Obama what advice he'd give his younger self
Maureen Cavanagh/ The Players' Tribune
Earlier this month, I had the incredible opportunity to sit down for a conversation with President Obama at the White House in the Roosevelt Room.
This isn't an interview, and it's not about politics. I simply wanted to share our perspectives on a few things that are meaningful to both of us.
We talked about retirement and our inspirations — and the President even snuck in a few good jokes on me.
Most of all, we shared thoughts about the importance of mentors and role models, and the work we both are doing through the Turn 2 Foundation and My Brother’s Keeper.
I hope you enjoy it.
You can watch the full interview on the The Players' Tribune here.
Business Insider has also transcribed it below with light edits for clarity.
Barack Obama: If you met me when I was ten, the first thing you’d think is, "he's fat," which nobody believes now. [Laughs]. I was husky, and I was kind of a smart-alecky kid. I was living in Hawaii at the time, and there weren't that many Black kids there. So part of what I was trying to figure out at ten years old was, you know, what kind of role models do I have for myself? My father wasn't with us, and I think that's probably part of the reason why I became so interested in mentorship programs and also trying to get it right as a dad.
Derek Jeter: Who are your role models?
Obama: Well, Dr. Jay, you know, he had a big poster and a big 'fro and he's coming in. Walt Frazier of the Knicks. I'm dating myself. Even at that age I loved Dr. King. But I can't say at ten years old that I was exceptional. I bet you were one of those kids who was the best athlete, even at ten, and everybody was like, “oh, Derek,” and all the little girls had crushes on you and all that. Is that true?
Jeter: No no no. I would like to lie to you because we're on camera, but no, it's not the case. I think when you're young your role models a lot of times are the ones closest to you, which were my parents. My dad used to constantly brag about how good he was at baseball. So when I was younger I wanted to be a baseball player strictly because my dad played baseball.
Obama: Now was your dad right that he was good in baseball? Or was he just making all these stories up?
Jeter: I don't wanna date my dad, but there wasn't a lot of media attention back in the day. You know, there was one newspaper, so he had his one book of his clippings. It was about two or three pages. So he used to sit me down and say, "one day you may have as many pages as this." So I think I got him. I passed him in Little League, but yeah, baseball was my focus.
Maureen Cavanagh/ The Players' Tribune
Obama and Jeter on strength
Obama: There are a lot of young men out there who are trying to figure out what it means to be strong, what it means to be tough. I want to make sure that we’re reaching out to those young people and saying, "you can be a leader." And even the kids who are most consistently getting in trouble I think can really turn their lives around.
Jeter: My Brother's Keeper is a remarkable initiative. You know, we've done some work with you guys, and I started the Turn 2 Foundation twenty years ago, and you know, our mission is to instill leadership in our kids. Academic achievement, positive behaviors, healthy lifestyles, social change — I mean, these are things that we feel are extremely important to our youth. Thinking about Muhammad Ali, who just passed away, and I’ll preface this with "there's only one Muhammad Ali." There aren't too many athletes — Jackie Robinson comes to mind, but there aren't too many athletes — that did what he did, had the social impact that Muhammad Ali had. There aren't that many people in general. So, you know, everyone can be a leader in their own way. They can have an impact in their own way. They can be their own person. And the kids are our future.
Obama: Yeah, when I talk to young kids and they ask me for advice, I say to find what you're passionate about and then just work your tail off. Success will come out of you putting your all into that passion. Being interested and engaged in life is the single most important pathway to success.
Maureen Cavanagh/ The Players' Tribune
Obama and Jeter on advice for your younger self
Jeter: At fifteen years old, I would probably just tell myself "continue to work." Because I think when you're younger you have this big dream. The big dream was ultimately make it to the major leagues. I grew up in the small town of Kalamazoo, Michigan. You have the dream, but you can’t really see it. And I would just tell myself to stay at it regardless of what people say to you and the negativity that you may hear. Just stick with it. I did something in my final season. I kept a little diary, and everyday I wrote something in there about how I was feeling after every game. I don’t know if too many people know about it. I’ve yet to look back at it. I don't have children, and I thought, “if and when I have kids..."
Obama: Dad actually had some game!
Jeter: Yes, yes. So it's sort of like my dad's scrapbook he had. Now I have photos.
Obama: It's a little bigger!
Jeter: Yeah. But I wish I would have done that throughout my entire career. There's so many experiences you have that you tend to forget. So if I could go back, I would say do it every day.
Obama: At 15, I would have told myself, "hit the books and stop goofing off." Because at 15 I was not the most responsible young man. I loved basketball, but outside of basketball, I was getting by on charm and wit and not taking my schoolwork as seriously as I could have, and when I think back now, I would say, "If I had just invested the time…"
Jeter: Things would have worked out a lot better for you.
Maureen Cavanagh/ The Players' TribuneObama: I might have made something of myself!
Jeter: And you would've lost weight. You gotta tell yourself you would have lost weight.
Obama: Well, at 15 I had slimmed down. I was about your weight then, you know, still a little chunky, but…
Jeter: [Laughs].
Obama: At 25, my advice would have been to lighten up. At 19 or 20, something happened, and I just got very serious. At that point, I graduated from college, and I was working all the time and reading all the time and had no social life. When I first met Michelle, you know, I had this old raggedy car, and...
Jeter: How old were you?
Obama: By that time I was 27. And 28. [The car] had rusted out so bad that it had a little bit of a hole on the passenger side, so you could see the street as you were driving by. So I knew Michelle liked me because when she saw that car, she wasn't marrying me for my money.
Maureen Cavanagh/ The Players' Tribune
Obama and Jeter on walking away
Jeter: Everyone always asks: is it strange after you retire? Is it a tough adjustment period? And for me it wasn’t. I slept. I don't think I got up the whole next day, so that's a very simple answer for me. I was ready to retire. I felt as though I put everything into my career. I got the most out of my career. And I was excited about new things to come. But that initial day you're gonna sleep a lot.
Obama: Listen, you're pitching, and I'm catching, man. Because that is my intention as well. I am going to catch up on some sleep.
Jeter: Now, me retiring and you retiring are two completely different things. So I stuck that with you.
Obama: No, Derek, you are somebody who now has some experience in hanging up the cleats here. And I'm about to retire. I'm not quite as young as you, but I'm still relatively young…
Jeter: Can you repeat that? When you're in sports they say you're old at 30. So thank you. I appreciate that.
Obama: Well, I mean, for a baseball player you were old, man. Let's face it. We saw you trying to run around those bases. But it was a charmed career and well deserved.
Jeter: Thank you.