meet derek jeter

Derek Jeter – Brand Ambassador

When you hear the name “Derek Jeter” what do you think of? You might think about a signature blue and white striped jersey with the number two on it, some of the countless records and awards he’s earned, the philanthropic work he’s dedicated himself to or the business ventures he’s undertaken, including being the CEO of a professional baseball team. But what do all of these things have in common? They all demonstrate Derek’s leadership on and off the baseball diamond!

Learn more about Derek and his dream pursuit (and achievements) and see why he’s an inspiration for dreamers everywhere.

American Family Insurance Brand Ambassador Derek Jeter at the American Family Insurance Championship

About Derek Jeter

Derek Jeter grew up in Michigan with a dream of making it to the big leagues. But Derek understood from a young age that wanting something to happen is never enough. To achieve a dream, you have to work at it.

When it comes to pursuing your dream, don’t let anyone outwork you, don’t let anyone tell you that you can’t achieve it, surround yourself with a great support group and believe in your dream. You have to believe it!

- Derek Jeter

And work at it he did! Derek remained focused through high school, college and finally the minor leagues before making his baseball debut at the professional level in 1995. But even with his winning mindset and eagerness to succeed, Derek still faced obstacles along his dream pursuit.

At just 18 years old, Derek had to deal with being homesick and experienced self-doubt as he faced challenges in the minor leagues. He broke through this adversity and learned that sometimes your failures can be just as valuable as your successes when it comes to achieving your dreams.

  1. Kathy Ireland: This is American Family Insurance ambassador, Kathy Ireland, welcoming you as we break through to dream fearlessly.

    On screen: Break / Through logo, presented by American Family Insurance.

    Kathy Ireland: Please welcome, to Break Through, Mr. Derek Jeter. Welcome, Derek.

    Derek Jeter: Thank you. Thank you very much. Thanks for having me.

    Kathy Ireland: Derek, there's a legendary story about you being away from home, the first time, being very homesick. And it was a time where you could either break down or break through.

    Can you share with us how you chose to break through?

    Derek Jeter: I was drafted when I was 17. I left the day after my 18th birthday and, really, the only time I've been away from home was when I went to see my grandparents in New Jersey.

    So, here I was going from Michigan down to Tampa, Florida, and struggling for the first time because, I never really struggled before.

    Kathy Ireland: What was the struggle?

    Derek Jeter: I got there and I was completely overmatched playing against the best players in the world. And constant phone calls at night, crying every night, being away from home, homesick — I didn't give up. I kept fighting, kept battling. And, you know, anytime I struggled from that point forward, I always used to say to myself, well, it's not as bad as when I first started.

    So, you need to experience success, but I think, more importantly, you need to experience failure.

    Kathy Ireland: Right — right. So, what would you say to a young person who is going through similar struggles and considering just giving it up?

    Derek Jeter: Keep fighting. You know, you have to have a short memory. And everyone's been there. And if they're telling you that they haven't, then it hasn't meant enough to them and they're not telling you the truth.

    Kathy Ireland: Derek, Sharlie shared with me that she was diagnosed with cancer in her senior year of college. And so many families are facing that tragedy. What can you share that will inspire, and encourage, people who are going through such challenges.

    Derek Jeter: Yeah, my sister — right before her 21st birthday — she was diagnosed with cancer. And when I was growing up, you heard someone had cancer, it was an automatic death sentence.

    Kathy Ireland: Terrifying.

    Derek Jeter: And that was it. But her strength that she had, instead of taking time off and going through her treatments, she wanted to have her treatments and still continue to go through school. I thought that it was very powerful. I thought it was encouraging to me. But she fought hard.

    And, you know, just to be there as a family. I miss my sister — I left when she was in the eighth grade — so I wasn't home when she went through high school, and then she's dealing with this. And you know, I'm in New York playing. So, we had a lot of phone calls at night. A lot of conversations that went very, very late. But any time I would struggle, I'd always say, well, how can I complain about what I'm doing on the field when I have my sister that's battling cancer?


Throughout his 20-year professional career at shortstop, Derek never stopped working to accomplish the next feat, the next goal or the next championship. His hard work paid off, and Derek’s legacy will live in baseball history forever as a 2020 Hall of Fame Inductee.

But Derek’s leadership didn’t stop off the field. He became CEO and part owner of a Miami-based professional baseball team in 2017. He’s also used his ability to motivate and lead others through the work of the Turn 2 Foundation, an initiative started by Derek and his father to encourage young people to turn away from substance abuse and “Turn 2” healthy lifestyle choices.

Being a good leader means putting what you say to action, and more importantly, get to know who you are leading.

- Derek Jeter

Ready to become the leader you’ve always dreamed of becoming? Check out these leadership resources inspired by influential individuals like Derek:

Meet Our Family of Brand Ambassadors

You’ve met Derek Jeter, but have you met the rest of the family? Meet our American Family Insurance brand ambassadors and discover how they help us inspire dreamers — like you!