Bloomberg Audio Studios, podcasts, radio news. The hardest part was having patience. You know, as a player, you get a hit, you don't get a hit. You win a game, you lose a game. It's instant gratification or failure. When you're building something, especially in organization, a sports organization, where basically you're turning something around right, you're going in another direction, it takes time that can be very, very draining mentally because you want it to happen right away.
Alex, this is one that I very much had circled on the calendar. Derek Jeter, I mean the captain coming in to talk to us. Who is Derek Jeter?
To you, well, he's a five time world champion. He was a teammate that I was lucky enough and fortunate enough to win the title in O nine with him. We played for almost fifteen years, about twenty feet away, and he is someone that I have a tremendous amount of respect. Look, we've known each other for over thirty years. I believe there's a third time in over thirty years
that we've been interviewed together, Wow, in any capacity. So I learned a lot listening to him, and I think the listeners will really get a kick out of this.
One, all right, So I have to fully confess I told you this before we'd sat down for this interview, like I didn't totally know what to expect, because as well as I've gotten to know you, a lot of headlines over the years and a lot of speculation about what the relationship was between you guys we fully address.
I think you know there was a rocky period in that relationship, and yet I will say, you guys tell some stories about those early days, you know, when you were still teenagers and what that was like sort of coming up together. And you know, one of my takeaways at least was no matter what happens, if you have that sort of foundation in a relationship, there's hope.
I thought you were going to say, even though you didn't like me, you liked him as a player. I was waiting for that because that is told to me all the time, you know, Jason. The interesting thing about Derek and I have a lot of love and respect for Derek. I think with time you grow a certain amount of appreciation. And I told him recently because we are now joined at the hip at Fox covering the baseball playoffs and World Series that I appreciate him even
more today than I did when we played together. Yeah, because what he showed the power of restriction, as I call it, is so much hard, harder to restrict than to act. Yeah, and he was really good at that. He had tremendous discipline.
The other thing that also occurred to me Alex as we were getting ready for this and then even in the conversation, was you guys have both made a commitment to stay close to the game. He went into the front office. He now is your broadcast partner on Fox. This love of the game and this sort of even shared experience after baseball is fascinating to me.
We're so similar in some ways, in opposites in others, and I've really admired the way he's transitioned in his post baseball career. And he went through ownership and management. I went to just ownership because I wouldn't know how to manage a basketball team. I'm really excited for people to get to hear this episode because one of my favorite ones on this episode of the Deal the Captain Derek Jeter.
Wait, so when did you guys first meet Heldria.
I was eighteen he claimed to be seventeen.
As a fact.
Where was it.
It was the Mark Lats Stadium, Michigan. Had come down to the University of Miami and he had signed to go to the University of Michigan. Was already a pro with the Yankees, and I was an upcoming draft and I had signed to go to University of Miami. So it was like Kitch school versus my school. It was cool. Wow. And I was talking to Casey Close at the time and really got to like Casey Close a lot. And yeah, I'm still no case who's been with Derek's hole.
Casey's my agent. Ye. We had actually spoke on the phone prior.
To really when people used to talk on the phone. Yeah, exactly what was it like back then for young athletes because it's not like you weren't following him on social media?
No, it was it was more of I was older. I think you know, Alex has always been inquisitive. He asked a lot of questions, which I'm sure you know. Yeah, when we spoke the first time, and I even remember is just asking some questions about my experience. I was trying to share some my experience just being a year older so there, I think there were some similarities when it came to that. Outside of that, well, I mean from Kalamazoo's from Miami.
So my memory, Jason is that obviously there was no social media, but for high school players there was this thing called Baseball America and this would come out of me two weeks and I remember I would take my mom and she would give me a couple bucks and we'll go to seven eleven. I would buy it, and a lot of times I would go early, three four days to see I wanted to read every piece of that. And I remember seeing Derek with this burgundy high school uniform.
I believe he had Nike high tops, and I'm like reading about this guy and he's like, okay, he's my color skin. He's from Calamuz, Michigan. That's strange. He's a first pick for the Yankees, right six pick overall, but he's six foot three and like, Okay, well if he can be a first round or well maybe I can too. Yeah. So I just remember being incredibly inspired and impressed that someone can be in Kalamazoo, play a much shorter season than we play in Miami and you'll still be the
number one pick by The New York Yankee. Thought that was pretty cool.
Yeah, all right, so we'll officially officially staright now. So Derek, if you would't mind, please introduce yourself. Tell us what you're doing these days.
Derek Jeter, What am I doing these days? Outside of being a parent. I have four young kids and doing some stuff commentating with Fox Sports alongside Alex, David Ortiz, Kevin Burkhart, a few business interests as well, a few companies that I've founded, boards that I'm on. I'm pretty busy. Yeah, you know, I'm pretty busy, but it's a good busy.
I think.
You know, when you talk to athletes, a lot of times when they retire, people think they just stay at home and they start playing golf and drinking wine all day long. As good as that sounds, I think, start preparing yourself for the next chapter. So keep myself busy.
Yeah, all right, we're going to get into all that, but I want to go back and start if I can partner with sort of where you'd left off in that story. It's like going to the Yankees. That's probably you know, this show is called The Deal, biggest business decision you probably make in your early life is or they make about you. You're going to the New York Yankees. Do you remember that moment.
And pass in a scholarship to go to Michigan, which is pretty impressive as it is.
Well, I think they made the decision. Yeah, you know, because in sports it's a crapshoot. You don't know who's going to draft. Do you have no IDEA Draft's a little bit different nowadays than it was when when we were drafted and we sit around a way for a phone call. So yeah, as Alex mentioned, I had signed to go to university in Michigan, drafted by the Yankees. Yankee fan growing up, the only team I ever wanted to play for, So in that sense, I was very fortunate.
Education was huge in my family. My dad got his PhD in sociology at Western Michigan University and Calm Zoo, Michigan, the reason why.
I grew up there.
It was really a decision. It was a big decision. It wasn't as easy of a decision as some people may think.
You know.
So I signed with the Yankees and they agreed to if and when I wanted to go to school, they pay for me to go to University of Michigan. So I went University of Michigan my first off season and still a freshman. So you've seen that movie Back to School, Ronnie Dangerville.
That's going to be me.
It's coming out, It's coming, it's coming soon.
But by the way, Jason, just to bring you back to nineteen ninety two, because I was watching from the sidelines in Miami. From Miami, you know, Derek was born to be a New York Yankee, and he grew up watching the Yankees, admiring the Yankees, wanted to be a short stop like Zoota and all of that. But what was interesting is leading into that draft, Houston had the number one pick and there was a lot of talk
that Derek would be one one in Houston. They actually ended up drafting the cow State Fullerton superstar in Phil Nevian. And then Cincinnati had the fifth pick and they also said they were going to pick Derek. They chose Chad Mattola, and then it fell to number six with the Yankees. So the Yankees got a huge break by having Derek be available, which no one thought he would be available.
Thank God. Yeah for me, Yeah no, because I was a Yankee fan. I didn't even know the Yankees drafted six. You know, Alex just sits at home because he was the first pick.
You know what I mean.
From the phone to ring, I'm sitting out there sweating it out, waiting to see who was going to draft me. So yeah, it's like a crap shoot. I never thought I would be drafted by the Yankees, but you know, luck was on my side.
I guess obviously you were a fan, but it's one thing to be a fan. It's an entirely different thing, I would imagine because I'm only a fan, but you put on those pin stripes for the first That's an entirely different proposition because now not only are you a Yankee, you're playing in the biggest stage. Did that feel weighty to you?
No, not necessarily. I think playing for the Yankees now it's a little bit different than when I first arrived. They hadn't had a lot of success. Yanks didn't won a World Series since seventy eight. You know, they haven't been to one, I think to nineteen eighty one they lost to La So I think the expectation level was a little bit different when I first got to New York and now, I think the expectation levels have changed.
They've risen because of the success of the franchise. But you know, when you get there, you don't I don't think you put that much pressure on yourself. You're trying to keep your job, you know.
I don't know if you remember.
We had a conversation. I think this was in nineteen ninety five, towards the end of the year. We're playing Seattle, and you had mentioned, Man, I wish they'd just give us an orientation year. We can hit to sixty.
Our first year and get comfortable.
You never had the orientation year, but that was our mindset. We just want we're there, we want to stay there. We do anything we can to stay in the major leagues. So I don't think I ever put that much pressure on myself with thought about it as being weight.
I don't know if you remember this one. I mean, we're here in La probably after that year ninety five, and we're both of going into our orientation year and we're in a cab ride and I think we might have both left our money back. That's when we actually needed to have cash and that right now, and we were just like, man, if we can just make a million.
Dollars in our careers.
If they put a contract right in front of me for a million dollars for my career, I think I would sign it with you. He's like, hell yeah, I man a lot of money. I'm glad we have a contract for or pen.
Yeah.
Wow. I mean it's interesting you say that, Derek, because baseball was at a different moment in the early nineties. What was the scene like as a player?
I would say, in my opinion at that moment when we first came up, baseball is the number one sport in the country. I really do feel that way. I think now, you know, basketball, NFL is taken off, but at that moment, I just think baseball was the number one sport. Yeah, and so many people played it. I mean we all played it when we were younger. So that's probably the biggest difference in my mind. And we just, you know, supposed to sport. Anyone can play any size shape.
You don't have to be seven feet tall. You don't have to you know, you don't have to be take this the right way. You don't have to be in the best of shape to play baseball, you know. But I just I'm a little biased. I don't know what you think about being a number one sport back in the early nineties, mid nineties, but that's the way I looked at it.
Everything just felt so big, and partly was we were teenagers coming up and we had a tremendous passion for the game. And I don't know if data supports us, but I certainly feel like baseball was number one. And I remember the nineties and when you guys started winning those championships, that wasn't just a New York story. That was like a global stories. I mean, the Yankees being back on top was so good for the health of the game of baseball. They're a little bit like the
Cowboys and Lakers. You either love them or hate them, but you never walk by and say, how do you feel about the Yankees. I don't have an opinion. Everyone has an opinion, and Derek was right in the forefront to lead those CHAMPIONSHI years, which is awesot.
Never ignore New York teams, right, you know, I think baseball's you know, once again, people are in sad bias, but I think baseball's in a better condition When the Yankees are doing well, when the Red Sox are doing well, when the Dodgers are doing well, when the Cubs they just won recently, when you have those big market teams that are having some success, I think is better for the sport.
And so picking up where Alex just was, you know, the team starts experiencing a lot of success. So what does that do for you in terms of seeing not just the business of baseball, but the business of Derek Jeter, Because then you get to negotiate some contracts and like, how does that evolve through the nineties for you?
Yeah, I think, like I said before, when you're young, you don't think about the business of baseball. You're just out there playing. Yeah, like Alex mentioned, we've re signed a one million dollar contract for life if we had the chance to do it. Because you're not thinking about the business side. I think you've sort of alerted or made aware of the business side once you start going
to arbitration. Yes, that's when you sit down and you understand how other people may feel about your performance on the field. I have a better understanding for it now because I was on the other side of it, or I should say another side. It shouldn't be one side or the other, it's another side. Of the sport. But I think that's when I realized that the business of baseball.
So what did you learn about that? Because you did go through it. You know, you went through arbitration. You were negotiating some pretty key contracts for yourself through the end of the nineties there.
Yeah, you know it was harsh. I think arbitration.
You ever go to arbitration, but I heard it's nasty.
Yeah, I mean going through arbitration for the first time, it's hard. You're actually sitting in a room looking across the executives from your organization and they're telling you basically how you're no good. Yeah, and you never had that understanding. You never thought they felt this particular way. So if you don't have thick skin, you can't go through it. Yeah, because there have been players that you know, you get
scarred by the organization, you never recover from it. I got scarred, right, but I was just able to hide it a little bit better. But yeah, so when you go through that situation, suation, that is a harsh lesson in business. And you know, my contract negotiations from that point forward, the long term extension I had, it really
wasn't that. You know, Alex did me a favor. He signed a long term deal before me, you know what I mean, So I sort of piggybacked off of his deal, but it didn't really get messy until the end of my career.
Yeah, and what about Steinbrenner, I mean on the other side of that table. I mean, we got to talk about George because both of you guys had a relationship with him. You had, you know, long term relationship. What did you make of him as a young person, and then as you went along, what did you make of them?
One he was smart, he wasn't in the arbitration room.
He kept the distance.
But no, I think Alex knows as well. In my opinion, he's one of the greatest owners in all the sports, you know, because he cared about the organization. He cared about winning. He would do anything it took to win. He was willing to pay the players, but he had high expectations. There's a lot of accountability there. He liked to challenge his top player to see if you could
take it. He would challenge you publicly. He would do you got theirs towards the end of the boss, you know, but when he was younger, he would challenge you publicly, and then he'd see how you respond. He'd walk into a clubhouse after a game, after a series. If you're playing well, he's shake your hand. If you weren't playing well, he'd look you up and down, shake his head and go to the next guy. That's just what he would do. But he wanted.
No question.
Yeah, yeah, there's a story. I mean, you know, stories of him and Well's going after it, you know, I mean, going after each other. So there's a lot of stories when it comes to the boss. But you have to have thick skin in order to survive in New York, and he demanded excellence and he wanted you to win every day. He was an old football coach, right, so you know he didn't really understand that in course of one hundred and sixty two game schedule you could actually
lose a game like that didn't It didn't translate. Something didn't click in his mind in that sense. We had the same mindset. You know, every game you play, you have a chance, you have an opportunity to win a game, and he expected that.
And there when it came down to, like your first championship in ninety six, I know how much that meant to him. How happy was he. I know how much he loved you and how much he loved him, and how special your relationship was. And like you said, I got there to a little bit of tours to end. Can you share some of the things that he inspired you with, that motivated you, that kind of bonded you.
Yeah, we used to always he lived in Tampa. I lived in Tampa for twenty some years. We used to always get together in the off season and we get together for lunch. And you know, he's a big Ohio State guy, a big Michigan guy, so we had that
rivalry to you know, compete with. But he listened to the players, not saying he listened to every opinion I had, but he would ask And I do think if you're in professional sports, if you're in an ownership position, you should listen to the players who are in the clubhouse. You don't have to make every decision based on their input, but you should at least hear their input because that's how you know the balance of things that are going on inside the clubhouse. Was good like that, and you know,
we had their relationship. He asked me about players, he'd ask me about not saying he listened to me like I said, yeah.
So take any names out of it, Derek, I don't need to mention names, but give me an example of how an example, and.
I'll and I'll give you a name. I remember in off telling, yeah, telling mister Steinbrenner that Louis Soho helped me more than any infielder at the time that I played with, or any coach. And he re signed Soho after that. Wow, you know, because Louis was a guy, you know, the best. Louie is the best, and I learned so much from him. And if you're in the front office, so to speak, you may not know the value that Louis Soho brings to young players in that clubhouse. But the boss wanted to know.
I'll give you a Louis Soho story. So I had him in Seattle and Louis like, you just got to love the guy. He's one of these guys. And Tim Rains is like this, you look at him, you start laughing. Yeah, he hasn't even opened his mouth, but he's so damn funny. Well, Louis has that in Spanish, right, He's Venezuela and I was nineteen years old. He was backing me up, whatever that means.
And he was forty five at the time. Forty five at the time.
And there was a play that I got as a short stop and I kind of a little lack of days ago and got it forced and we couldn't get the double play. You know, I'm nineteen. I think I'm pretty cool. We're playing at the Kingdome. So I come in like running around and he's looking at me like giving me a bad look. And Louis never gives you a bad look, and he's like, what were you doing. I said, well, I got the forest, I got one out. He was no, No, He's like, screw the you gotta
get too. Attack that ball and give him a good toss and get too. We need to outs there. And I'll never forget that, because the point is if there's an opportunity to get to get to and sometimes a player can tell you that and not a coach. Right. And I'm glad that he was such a leader for you as well, because he really changed my career.
What did he do specifically for you?
We'd work every day in ground balls. He made it fun. You play every single day baseball for a reason. One hundred and sixty two games. It didn't get monotonous. You know, you have to have fun with it, but have fun but same time work extremely hard at it. And Louis was big on that. He made it fun though.
Through the nineties. Obviously, you guys are are keeping in touch. You're sort of taking a look at what he's doing. You guys are playing each other now and again. This is called the deal. So let's fast forward a little bit too. He shows up in New York. There's a pretty important deal that has to be cut at that point because he's also a short stop. Do you remember how all that went down?
Yeah, well I wasn't a part of that deal. You know, when mister Steimer and had called and said that we were signing Alex, he said, we're signing Alex as a third basement, which I never thought would happen. I mean, why, if you're him, why would you switch positions. I guess he really wanted out of Texas, so he's willing to play anywhere. But it was never a deal, no one ever, and I give it to him. He never asked to
play shortstup, never brought it up. I never heard any whispers about it because he had committed to play in third base, and that's what I was told at the time.
Yeah, it's interesting. My side of that story is Tom Hicks, who was the owner of Texas, was having some financial situation where he needed to move some contracts around. And I remember walking into his house on a Saturday morning after the season, and I think the Wild Card was game. We were watching Minnesota and his Oakland in his home in Texas, in his home office, and he said, Alex, I need to trade you. Can you give me three teams?
I said, okay, give me to a Monday. And I called him back Monday and I said Red Sox, Angels, and Mets. And I said the Mets was really interesting because I grew up watching Magic versus Bird and the first thing I would do in the morning is see what Derek did in the old box score when we had to read the papers. So I thought, me going to New York would be great for baseball. I would be with the Mets, he's with the Yankees. Were both shortstops. We both like the Angels. We always have great weather,
great places to play. And then the Red Sox was like, okay, that's a good rivalry too. I worked in the Red Sox deal for two months. That deal literally at the one yard line, fell apart, and Cashman at MVP dinner said, hey, if you're willing to move to third base, maybe we'll make something happen. Well, I'm not a big drinker. I was three focus in.
I'm not a big drinker. Now changed the record.
It's a little blurry. And then by my third cocktail, go yeah, maybe I'll play third base, And two weeks later it happened that quickly. So it just happened within ten days.
I mean that the core of that group that got together, obviously, you know some things happened in between. Then do you want a world championship? When we come back, we discussed Alex and Derrek's two thousand and nine World Championship, preparing for life after baseball and lessons learned owning and running the Miami Marlins and yes, one of the most talked about relationships in baseball history. The core of that group that got together, obviously you know some things happening in between.
Then do you win a world championship like it? And after another little spell of not what does that championship do? In your mind? You know nine it.
Is hard, man, I mean, winning is hard. It's difficult to do. There's been plenty of years before two thousand and nine, we thought we were going to win a World Series. We thought we had a team that was going to win, no doubt me can go to two thousand and four, we had three zero lead against Boston. We thought we're gonna win a World Series. So it is hard to do. I never took it for granted. I know Alex didn't because he hadn't won it before then. But it's a lot of work.
Man.
It really is a lot of work. So I don't want to say you exhale. You can exhale for a minute, but then you have to get ready for the next year. But every team is different, you know. With the group of two thousand and nine, with some new players, he had CC with AJ we had texts, but some of the guys that were there before we had been through some losing seasons. So man, it was a good feeling.
I'd tell you For me, Jason, I remember giving Derek a big hug at Yankee Stadium, but it was so much relief. I certainly excelled because I had played fifteen years and ultimately I mean, I would have been absolutely heartbroken to move position, to come here for the greater good of the team and to come up short. Remember I grew up watching Dan Marino and Charles Barkley, two of my favorites, right, and it breaks my heart to
this day. They say they yeah, but and it was just complete validation and I was just so thankful to God to put this thing to come true, you know, as a great baseball fan. It was the greatest threw of my baseball career by far. And I would move to third base one hundred out of one hundred times to be part of the Yankees championship run that year.
One thing, you know that Alice was talking about switching positions and finally winning a championship. We didn't the guys that were there before. I say we There was a few of us that were there before. We also didn't want at the end of our career say, oh, well, we were lucky. We won four on that lucky but we won four out of five our first five years in the big leagues and that we couldn't win again,
you know. So it's the thing in New York is it's a constant reminder every single day that you have not won, you know what I mean, It's like, you gotta win this year.
You got to what.
They don't care what you've done in the past, which is a great the reason why I think a lot of people can't play in New York. You can't deal with the expectation level. So we were constantly reminded from two thousand up into two thousand and nine. So you get tired of hearing the fact that you haven't won in nine years. You need to win again. And I think you know, New York is a hot spot. You talk about the business part of it, New York is
a hot spot. So when you win, I'm sorry, it elevates everyone at that point, you know, because I've always said playing Yankee stadiums like performing on a Broadway play. You feel like it's the top ticket in town. You know, you feel like the lights are brighter. Everyone comes out, every celebrity, you know, every entertainer is there to watch the Yankees play. And the reason they show up is because you win.
One thing I've always marveled at, Derek. I've gone through so much in my life through therapy and all that kind of stuff to really it was I'm forty eight, and I was around forty five where I look back at Derek's Korean and I said, holy, I really got an opportunity. I never thought we would ever get close again, because we've had, you know, you know, our setbacks, partly
because of my shortcomings. But I said, I really have an opportunity to appreciate what an incredible career you had and to be in the greatest city, the biggest market in the world, but yet be a little bit unknown of what's going on off the field. And I remember how much I failed and tripped, and the more I tried, it was like quick sand, the deeper I will get myself into it, And was say, Alex you he would
say two things to me. All you gotta do is make contact, dr dance so damn strong, and stop striving out. And then he would say to me, you don't have to tell them anything. And when he told me that, it makes sense. How the hell did you do that and do it so well?
Well?
I always wanted to have a separation with what I did publicly, my job, my career, and my private life. I truly believe once you let the toothpaste out of the tube, you cannot put it back in. Once you give people a little taste of what you're doing in your private life, they want more. They want more, they want more, and they feel as though you owe it to them. Now I understand it. I was just never
comfortable sharing my private life, you know. I always wanted to keep it to myself because my job came first. That was I wanted no distractions. And I also understood, you know, when you're playing profession sports, I knew I did not need the media to do my job. Eventually, they're going to need me at some point, right, So if I went out and performed on the field, I didn't have to worry about what anyone said because when
I wasn't opening the door to my private life. So only thing you could talk about or confirm was what I did on the field. And I just had an understanding of that from a young age. I don't know, I don't think anyone told me it. I just knew that I would try to do whatever I could in my mind to limit distractions. I would address something once that's it, I wouldn't talk about it again. The more you talk about it, the more the story continues on.
You know, people would ask us about our stud I would address it one time, don't ask.
Me again, and I would talk about it every week and he's like, dude, you're killing me, Like you don't have to answer. He was great again. I mean, by the way, stuff I would never talk about publicly to anyone. But there was some real stuff that I was going through my life that he gave me the greatest advice
and I didn't listen and it hurt me tremendously. So my point is, over the years, I get to understand Derek Jeter's greatness as a human being so much more than when I played, because I was just too close to it, and quite honest, I didn't have the tools. And that's not an excuse. I really tried. I just didn't know what the hell I was doing. I was pretty good on the field though, that's where I shined.
You know, were you frustrated with him when he didn't listen to you?
Well, I would only say frustrated if it became a big story. Yeah, Well if we're talking about things that didn't matter on the field, not just with him. I mean it could be anyone. You know. That was frustrating because I wanted when I got to the park to the stadium. I wanted the conversation to be about the game, and that's it.
Yeah.
And so in your business life, one of the really interesting decisions you make, and I feel like this is actually of a piece, is to go with Jordan Brand. I mean, that's a big decision on your part. We're sort of early in the game. I think it's fair to say tell us about that decision, because that's seminal not just for you, but it's candidly seminal for that brand too.
Yeah. You know, I first met Michael in nineteen ninety four while he's playing baseball in Arizona Fall League.
Wow.
And I'll pointed out he was not as bad as everyone rights him out to be. I mean, you take off what since little league, and then you're playing baseball at thirty years old in Double A you hit two hundred.
That's that's not.
A contract today. That's pretty damn Yeah. It's not easy to do. So it was not as bad as everyone says. So I first met him in Arizona and we just developed a relationship from there. He's like a big brother than me, you know, like magic is to you. I know, you speak highly about magic all the time. He's one of the first athletes alongside Magic that really took their
abilities on the court and it translated into business. They had the business mindset because you know, up until that point, I'm not saying anything about previous athletes, but it was all you just perform on the court. You perform on the field. When your career is over, that's it. Go get them figure something else out. I think those two were business savvy and they thought about post professional athletic career.
And you know, Michael's been as successful as anyone, and he's been a mentor to me since, like a big brother, like I said, and just thankful. He asked me to be a part of the Jordan brand, and you know when it first started, like, what do you mean part of the jitsu basketball brand? What is a baseball player going to do?
Right?
But he wanted me to be the baseball player and help him build the business.
So did it feel risky to do that, to be like the first baseball player to.
Do that, Well, I think risky. I mean, if you're going to take a risk, I think you take it with someone like Michael, you know, So I don't necessarily think it was risky on my part, you know. Plus it was the cool factor, you know, I mean everyone wanted to be associated with Michael back then and now yeah now too. Yeah, you're right at the point, same thing. So I didn't look at it as being risky.
Yeah.
So let's shift to sort of post baseball, and you know, we talk about about this a lot, and Alex has shared some of this before. But that moment when you decide to retire, I mean, there's the decision, and then there's the execution and the moment when you are no longer a professional athlete, You're no longer a New York Yank at least as your job. You'll always be New
York Yank here, et cetera. But what is that moment, Like when you wake up that morning you're like, huh, okay, the decision or afterwards tell us about the decision and then and then.
Well, the decision was not a difficult. They would have got rid of me anyway. They're trying to run me, run me out, So I don't think the decision.
Was joined the club. Yeah, the decision, Yeah.
The decision wasn't a difficult decision. You know, it's I'd broken my ankle twice. I've basically missed the previous year, and I wanted to have one more. I want to play a season healthy. So I called hal Steinberner and told him, and he said, look, you know you deserve to announce it any way you want to announce it. I announced it before the season started because I knew if I did not that I'd be asked about it all the time, you know, every single day my teammates
would be asked about it. So I announced it before the season, and then when the season was over with man, I was tired. You know, I really was tired. It's twenty years in New York. I've jokingly says, like dog here, it's one hundred and forty years playing in New York. I got everything I could get out of my career, and physically I was, you know.
I was.
I was done.
What's your business mindset at that point, because obviously you've been thinking about it for a time. Your partnered with with Jordan Brandon, those sorts of things, and we've talked about this. You're in New York, so I mean you have access and you know, beyond name recognition, you have sort of access to a lot of corporate minds, investment minds, et cetera. What are the first few things that you think about doing well?
First?
I didn't start preparing for post playing career the day I woke up the next day. Right afterwards, I started preparing for post career years in advance. My biggest fears in life is being unprepared in anything. You know, a lot of times you hear athletes say game slows down or it speeds up. I think it speeds up when you're unprepared. So I didn't want to wake up and say, what am I going to do next? I started talking about team ownership maybe ten years left in my career.
During my career, I made every decision when it came to contract negotiations, marketing, philanthropy, atum on foundation. These are all pillars of an organization. I lived in Tampa. I learned about player development and scouting and analytics, so I wanted to be as prepared as I could. I started a company called The Player's Tribune. We actually launched right after my career. But I didn't just wake up and
say let's start a company today. You know, you start thinking about these things, and that's why I think that it made my transition into the business world speak a lot easier because I started preparing and I started learning for it.
And Derek, when you talk about the Marlins, THEO, that team that went to the playoffs this year for the Marlins with very very limited resources, has your handprints all over it. The pitching, the development, the people you hired. And I was in the community and I just heard all the great things you were doing in that community. What would you say was the hardest part and the best part of being CEO and owner of the Marlins.
The hardest part was having patience because you want things. You know as a player, you get a hit, you don't get a hit, you win a game, you lose a game. It's instant gratification or failure. When you're building something like especially in an organization, a sports organization, where basically you're turning something around, you're going in another direction, it takes time. That can be very very draining mentally
because you want it to happen right away. And that was probably the heart this part is trying to have some patience.
I don't have a lot of any more time with limited resources. Yeah, and not against your partners, but that market it could be very, very challenging. Yeah, if you were in New York or Boston or the resources are just tremendous and you can actually expedite it a little bit. But here you had to be very clever, ready had to roll up or sleeves.
I figured, you know, we played in New York. You show up at Yankee Stadium. There's fifty thousand people there. That's just how it works.
You know.
One of the first things I did when I was CEO in Miami was I brought every single member of the front office by department into the clubhouse and I introduced them to the players because I wanted the players to see how many people were working behind the scenes to make their jobs easier. Everyone said, you know, how long they've been with the organization, what exactly it is
that they do. There were employees that had been there twenty plus years and never stepped foot in the major league clubhouse.
Now.
The employees thanked me, but the players also thank me because, like I said, you don't understand that part of it. So building an organization and taking the time and spending the time I expected that. You know, when you care about something, you put in the work. It took a long time to try to develop trust. You know, I can't walk in the room and say trust me. You don't know me, right, So you got to get to
know a lot of people. Spend a lot of time in the Miami community getting to know a lot of people.
I'm in Miami.
I'm not moving now, I'm there, So I'm happy that I had a chance to do that. But that's a part of building an organization that people don't see the stuff that goes on behind the scenes.
And so you exit that situation. How do you look back on it and how does it influence what you do next?
Oh? Man, how do I look back on it? I take the good with the bad. I think you learn a lot of lessons. I'm happy with some of the hires that I had. You know, I wanted to have a diverse front office. I was able to accomplish that. I didn't do it because I wanted to focus on it. I did because it was the right thing. You hire the right people. You give people opportunities. I was given opportunities throughout my life. You want to return that. So I look back with you know, I try to focus
on the positive. I'm positive by nature, you know, so there's a lot of things that we accomplish that I'm happy with. And those are some lessons that I've learned. There's mistakes that have been made. I won't make those mistakes again.
If there's ever another opportunity with what you learned, and I'm sure, I mean, there's nothing you can do because the reputation you've built and your track record speaks for itself. If an opportunity came calling, and let's just say it's not a smaller market, let's just say as a mid market or even a large market, and they wanted you to be the owner and operate, again, I.
Don't have enough money.
My question, and to be honest, would you want another crack at it? Would you be open to it? Ah?
Man, you know that's a tough, tough question. You never say never, but you have to be there, you have to be present. And I have four young kids now, man, and I understand how difficult it is. And you know, you want to get into a situation where you can make decisions, make all decisions, and unless you have a controlling owner ownership stake, you can't make those decisions. So that's a tough one to answer. But you ask me now, now.
And Derek, how do you think about investing? Does investing excite you? Are you someone that picks up the phone and calls a Michael or calls Pasada or one of your friends? Do you share ideas? How do you think about investing when opportunities coming away? Because there's going to be viewers that are going to say, I would love to have my hero Derek Jeter invest in my company. I'm a young founder. How do you think about that? How do people approach you? How do they find you? Yeah?
I think one of the benefits and perks of playing in New York is you get a chance to meet a lot of people. I've met a lot of people throughout my careers. I still get a chance to meet a lot of people. The way I look at it, Alex is I invest in people. You know, you run into people all the time. They have great ideas. Everyone has a great idea. Everyone has a business is going
to be a billion dollar business. But you have to invest in people, and you have to get to know them, and you have to know if they're passionate about what they're doing. Some people have businesses where they're in it to make money. Look we all want to make money, but if that's your number one priority, if you're not passionate about it, then I think that's a red flag. So I always like to invest in people. I think that works for you know, works in clubhouses, and it
works in businesses, it works in investments. So I tend to just lean towards the you know, the character and the passion of the people.
So one of the more recent decisions that you've made is to join the commentating world, which I believe you had initially said no interest there. Now part of it was you were an owner and CEO of a team. What drew you to the commentating booth.
I'd been asked that question before and I was absolutely not I'm not doing this. I went to World Series last year and I was just on the set with these guys Philly, Yeah, for a few minutes, you know, and just saw how much fun they were having, you know. And one thing that I never wanted to do was to get into a situation where I had to be overly critical of players because I know how hard it is to play the game, and I saw how much fun they were having, and I was asked to be
a part of it. And I said, hey, you know, as long as we can have fun with it, I don't want to be overly analytical, which I know he agrees with, and just really get a chance to shine a light on the sport.
I love baseball.
Yeah, I really do love baseball. I think it's the greatest game in the world, and if we have a chance to shine a light on it, then I'm all for it.
And Alex, you and I have talked about this. I mean, it does feel like this has been we may look back on this as a really critical year in the history of baseball rule changes. I think the storylines that have been really good. Do you agree with that? I mean, is there something that has happened and what is it that is sort of causing a little bit of a Dare I say rebound for baseball?
Yeah, Baseball's lag behind other sports. You know, you go through the history of other sports, NFL, NBA, There's always rule changes. There's always is a three point shot, there's all. You know. You change the rules for the betterment of the game. And no matter no matter how you look at it, it's entertainment. You get the fans watching. You have to listen to the fans, and I think the fans in baseball were saying, look, one, the game's too long. You got to find a way to speed it up.
So I think Baseball deserves credit for making some rule changes and I'm sure there'll probably be more adjustments along the way.
Well, and kind of stitching that back to something you were talking about a minute ago, Derek, is you know you show up on set last year, you see these guys. What's it been like sort of working with with the crew.
I'm new man, I mean, this is this is I'm new. I mean seriously, the first game we're in London, they threw me on at the desk like five minutes before. I can't even figure out to get my ear piece in it. I have no idea. They're talking in my ear and I'm trying to answer them, and I'm like, I'm not supposed to be answering them, you know. So it's it's a learning experience. I think you get more and more comfortable as you go through it. Alex is a pro. He's been doing it for a long time.
He enjoys it. I remember when we were playing I used to tell them, you know you're gonna get into you know TVs, Oh no, for never. On every channel you turn, he's here, he's doing a game there, So he's yeah, he's doing everything.
You can't shut me up. That's never changed.
So it's you know, it's you learn, you know, you know, you hope to get better. I know I've made mistakes, but ultimately you just want to have fun. You want the viewers watching to have fun.
I've been asked about a lot of players, obviously none none as big as Derek. So when they approached me about, hey, what do you think about Derek? Would you be okay with it? I'm like, of course I'll be okay with it. You know, that's something that he has to figure out if he wants to do. And they were asking me basically, what's the scout report, you know, pitching. We say, hey, we're facing Jason's like, what does he got right? And I said, look, you're never going to find someone that
is more prepared. You're never going to find He'll never be unprepared. So he's gonna come ready to play every day. He understands entertainment, he understands being part of a team. He has a really good relationship with Big Poppy, my relationship is solid, and he's gonna love Kevin Burkhart, so I think he'll fit great. And you know, obviously they got to talking, and so far he's off to an amazing start. I'm actually in awe of how quickly he's adjusted,
because it took me a while to get going. I mean, he's probably at the two week mark where it was at the two year mark. So I'm excited. We're going to have a great run. And by the way you said it best, we're talking and highlighting the greatest baseball players in the world. We've had a phenomenal year and our job is to be an extension of Rob Manford and Tony Clark and all the great things they're doing, and we get to do it in a national stage when everybody pays attention.
And you know, the other thing, when you're talking baseball, this is this is what the way I try to look at it is. Whatever we say is not wrong. It may not sound right, it may not come out right, you may not articulate it well, but it's not wrong. It's your opinion. Yeah, And we played the game for a long time and people don't have to necessarily agree with our opinions, but it's not wrong.
Yeah. One of the lessons I learned, and again Derek and our opposites, like I've made every mistake in the book. He doesn't make it. He doesn't make a lot of mistakes. But when we're out there, to Derek's point talking about players, managers, front offices, the lesson I learned is you can be critical as long as you're not personal right, and you can say something like, look, I think Jason's one of my favorite players, but he's had a rough week, and if you ask him, he'll be the first one to
admit that. But here's what I think Jason's going to do. I think he's gonna do X y Z right versus taking a personal shot. And I think that's a that's a really fine line. You want to stay in the other in the right side of that, all right.
So I got to say, you don't have to say, but I'm going to say. So when I saw that you were coming over and you guys were going to work together, even you know, when I came in here today, like, how's this going to go between these two? Because there is history there. You guys seem good.
Why don't people need to put it to bed. I think at some point, Jesus, this was one something you have known him for thirty years, you know what I mean. And I get asked more about our relationship than I do my wife.
That's scary.
Yeah, I mean, it's just put it to bed. I mean, we said we're fine working together again. You know, you can't change history. History happened, right, It's over and done with.
You move on. What's funny our partners and Hannah and Jack, I think they're happy that we're in this place. I've had so many New York Yankee fans come up and say, I'm so glad that you guys. I don't care if you're best friends. I'm just glad that you guys are working together.
Yeah.
And when they have their hero and someone that they admire together, that one together. I think it's warming to their heart to know that we are getting along. Yeah, that's my thought.
And so when you think about I mean, and this is a question for Derek, and I don't know if you and I have ever really talked about it. Alex, you know this idea of playing for the Yankees, I mean, it does it hits different? And so what do you think about as your life, see especially as a Yankee as you look back twenty year career there, like what jumps to your mind? What do you think is the most important thing. What's the thing that you want to be most remembered for as a Yankee?
Oh, I mean you want to be remembered as being a good teammate, you know, you want to be remembered as winning obviously who you are on the field, I think off the field. But for me, I've always said the only thing I care about is being remembered as a Yankee because it's the only thing I wanted, the only team I wanted to play for, only thing I wanted to be remembered for. So I'm fine with that, you know, I'm fine with that. That's that's if my legacy is just being a member of the Yankees.
I'm fine. Yeah, And I probably share this with so many Yankee fans around the world. Like, just playing twenty five feet from Derek, regardless of what's happening, with the noise that I created, it was such an incredible feeling. Again, with time and perspective, it makes you appreciate it even more that the guy that was playing next to me was always going to be prepared and ready to play,
and that meant so much to me. And I think no matter what the relationship has happened, like that mutual respect on the field has always been I think one hundred one hundred. We had that commonality about we both want to win at the highest level. Like I never had to worry about Derek playing hard or running hard or did he watch film? Never And that's something that to me, I always underscore.
One of the most fascinating things about athletes at this point in their career as former athletes, and Alex and I talk about this all the time, is you've got all this time when you leave the game ahead of you. I say this because we're roughly the same age. You're a young man. What's your legacy for this part of your career and your life?
Hmm.
That's a good question, because you say, you know, when you're an athlete, you turn thirty, everyone starts telling you old. Right, you retire or retired at forty, and then you're young again, right man. Now, the only thing that matters to me the most is being a good parent.
That's it.
I'm biased my parents. The best thing I can say about my parents, is they were present. You know, I want to be there for my kids. That's the number one priority for me. It really is. I'm not just saying it. It is the number one priority for me is to be there with my family, with my kids, help them find the thing that they're passionate about. I don't care what it is. I just want them to find something that they're passionate about. I want them to work extremely hard at it, and I want to be
there to support them. So I think that is number one for me.
This has been amazing. Thank you so much. Thank you both. I mean, we're doing this together, but I feel like I learned a ton about the Yankees that both of your business ambitions, and really appreciate you being as candid and thoughtful as you as for having me.
I appreciate it.
Thanks a lot.
Thank you.
Captain The Deals of production from Bloomberg Podcasts and Bloomberg Originals. The Deals hosted by Alex Rodriguez and Jason Kelly. Our producers are Victor Vees and Lizzie Phillip. Our story editor is Sir Dartha Mahonta. Our assistant producer is Stacy Wong Blake Maples is our sound engineer. Rubob Shakir is our creative director. Our direction is from Jacquelin Kessler. Original music by Blake Maples, casting by Dave Warren. Our editorial supervisor
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