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Randy Wilkins puts Derek Jeter's life, baseball career in focus with "The Captain"

"The Captain" is a seven-part documentary airing on ESPN
"The Captain" is a seven-part documentary airing on ESPN

On the heels of the pandemic era smash hit “The Last Dance” about Michael Jordan and the Bulls dynasty, ESPN is about to spend several hours bringing another recent sports titan into closer focus. From director and producer Randy Wilkins, “The Captain” is a seven-part documentary about Derek Jeter, the five-time world champion who defined an era for the sport and the Yankees, the only franchise he ever played for.

“The Captain” debuts on ESPN July 18 and runs through August, and offers an inside look at a famously private superstar.

As we speak, I've seen the first five episodes in the series. First of all, congratulations on it. I'm really enjoying it.

Thank you. That means a lot. I appreciate it.

So how did this project come to you in the first place?

Bit of a long story that I'll try to keep as short as possible. Back in 2020, right when the pandemic was raging, it was June, I believe I got a call from Spike Lee, who is someone that is a mentor, fellow collaborator. I've known Spike pretty much my entire adult life. I used to be one of his editors and was an assistant editor. And that was also one of his students at NYU grad film. He called me and asked me what I was doing. And I said trying not to catch the virus and you know, just laying low. And then he asked me immediately who was my favorite Yankee? And I said, Derek Jeter and I was completely thrown off by the by the question, it just seemed like it came out of thin air. And he said that Derek was interested in doing his own documentary, and that Spike was putting me up as a candidate to direct it. And I almost dropped the phone. I couldn't believe it. And a couple of days later, I met Mike Tolan, who was the producer of ‘The Last Dance.’ And then a couple of days after that I was on a Zoom with Spike and Derek and had a great conversation with Derek. I think that he was looking for somebody that understood the game of baseball and had some idea of how his career went. And we hit it off right away. It felt like I knew Derek for about 10 years. And a little bit after that, I got the gig. And here we are.

It's great to notice, given your background, that Spike Lee does appear in this project from time to time in the stands. So that's one added bonus for you.


I have to imagine there was some trepidation on your part to take on a project like this, given the fact that Derek  famously guards his privacy. And part of I think Episode Five even deals with that dynamic. So how did you look at the challenge before you when you started working?

Well, on that Zoom call that I just mentioned, we had a conversation about it. And it was pretty clear that Derek was ready to talk. And he was ready to step outside of that public persona that he had constructed for himself during his 20-year career with the Yankees. And obviously, as a filmmaker, you want to tell the best story that you can, and that includes the subject of the documentary being willing to be open and honest and vulnerable. And in that Zoom conversation, there were there was frank dialogue about Derek's willingness to do that. And by the end of that call, I was extremely confident that he was ready to speak. I think that he knew that if he was going to do this, that he was going to have to open himself up. And I think he had conversations with his family, conversations with his agency. And yet, he had also seen ‘The Last Dance.’ So I think he knew what was required in order for this to be a compelling film. So by the time that that Zoom was over, I didn't have any more trepidation. I think the biggest thing was just convincing a studio or a network that Derek was willing to talk. But I felt armed knowing that from the man himself, he was ready to do it and all of my concerns kind of dissipated. And I think that that shows itself in the film.

What about when the cameras started rolling? We do see archival footage of him dealing with the New York City tabloid press corps over his career. Were you able to make a connection once you were sitting in the same room and trying to ask him about, sort of, sensitive things from his career?

Yeah, but I think that you establish that connection before you get in the chair and the cameras are rolling. If the first time you're speaking about these things is when you're on set and you're calling action, then you're probably not going to get as much out of the experience as your intentions may desire. So a lot of it is building a trust and a relationship before you shoot the first frame of the film. So Derek and I spoke for over a year, just getting to know each other. I went down to Miami when he was with the Marlins. We hung out at a game. And we just had conversations about what he wanted to talk about, what I wanted him to talk about, what I wanted to cover in the film. And we were aligned, pretty much from the beginning, there were even things that he brought to my attention that I knew nothing about that he had never shared it with the public that ends up in the film. So it was a collaboration from the beginning. But the key to that is having conversations before you sit in the chair. Again, if you're hoping that he will say something when you're rolling the cameras, you're probably not putting yourself in the best position. So a lot of this is about preparation. And for Derek, he believed in preparation. That was kind of like the cornerstone of his career — preparation and being ready for every possible scenario on the baseball field. So we were aligned with that philosophy. And I think that it shows in the film.

One thing he says in the project is he's always had trouble living in the now and appreciating the moment. He's always focused, hyper focused, on what the next thing will be. So why is it that he wants to look back at this point in his life, do you think?

I think the biggest thing is he has a family now, he has three daughters. He's married to his wife, Hannah. And I think at this stage of his life, I think it was really important for him to share something with his children. They weren't around when he played because he didn't want to be selfish with his future children. He wanted to dedicate his life to them when he had them. But he knew that baseball and his career came first. So his children didn't have the opportunity to watch him play. So I think that one reason he wanted to make the film was to have a record of all of his life prior to his children being with them. So I think that that kind of impetus allowed him to really think about all of the moments that he had, the experiences that he had, the ups, the downs. And I think while we were filming, and going through the cuts, I think it also slowed him down because he remembered a lot of things that he might not have remembered at the moment because he was always focused on what was next. So I think that this has kind of been a journey of self-discovery for Derek. But I think the emphasis started with his children.

It strikes me that you picked a very interesting timeline to deal with. I was thinking about how Jeter compares with the current Yankee superstar Aaron Judge, who's come up in a time of social media and sort of 24-hour access to content about the team and the players. With Jeter, it was sort of before all of that, and maybe, you know, in his career, smartphone use kind of came up right along him. So what was your process like as a director to find the archival footage and maybe forgotten footage from earlier on in his career?

The biggest thing was just building a foundation off the baseball career. That's what we know Derek for, obviously. He transcended the game, but at the heart of everything, he was a New York Yankee that had incredible success on the field. So I think that we had to honor that know that there are a lot of baseball fans that are gonna watch this. But for us, it was kind of striking that balance for baseball, and non-baseball fans, like Yankees fans and non-Yankees fans alike, but the foundation of building out the structure of the story was his baseball career. And then we used those moments as touchstones to figure out, OK, where did the personal things fit along this timeline of his career? So once we built out the baseball structure, we knew that there were opportunities to talk about this part of his life, this part of his life, this this part about New York City, this part of our celebrity, so we were really guided by his career. And then we just found the moments where he felt it was appropriate and seamless to get into more of the personal stuff. So it wasn't necessarily going by the cultural timeline. It was the baseball timeline, and that would dictate to us what part of Derek's private life, personal life and the larger cultural stuff we can include in the film.

Among the many people you interview in this project are his parents. People will remember seeing them watching his playoff games and sitting in the stands. But I think you get an understanding of just how important his family was to his development and his later career. What did you learn about Derek's family and how they experienced his life?

Derek's parents are two of the toughest people I've ever met. We have to remember they were an interracial couple not too long after the Loving case in the Supreme Court and to be able to function as a couple, function as a larger family, given the cultural context that they were living in and raising a family in, it's just a testament to their belief in love, belief in one another, their level of toughness, how much they care for one another. So I think that that toughness was passed on to Derek and his sister Sharlee, I don't want to forget about his sister as well. But I think that his parents are incredibly tough and incredibly loving. And firmly believe in family. And I think that that was passed on to Derek. And that allowed him to overcome a lot of things both on the field and off the field. And I think that it created that hyper focus. And I think it created that competitiveness. But it also created that toughness, it created that awareness, it created that ability to navigate through New York, that ability to navigate the pressures of being the star shortstop of the Yankees, but also being a biracial Black man, how to navigate having that cultural identity in America. So I think that his family truly is the bedrock. I think that they created a roadmap for him. And I think that you would not have Derek Jeter without his parents.

I want to go back to what you just mentioned about his sense of competition here. He has an insatiable desire to win. And you've done, obviously, other athletic projects before and you interviewed a lot of athletes for this particular project. How uncommon was that among his peers in baseball at that time?

I think it was uncommon in the sense that it was relentless. Like, there wasn't a moment where he kind of pulled it back. And I think that there were moments with other athletes where they're satisfied, or they kind of rested on their laurels, or they take a moment to think about what they accomplished while they're still playing. And Derek didn't do that. Insatiable is the perfect word. I think that he just had this innate need to win. And it wouldn't allow him to think about anything else. And I think that everything he did was centered around winning championships. And I don't think that every athlete thinks that way, especially in the professional ranks. There's money that's involved, there are temptations. There are a lot of things that come along with being a professional athlete, there are a lot of perks that are attached to it. And that was all secondary to Derek. For Derek it was winning at the highest level and winning as much as you possibly could. So for me, he's Tiger Woods. He's Michael Jordan. He's one of the greatest competitors in American sports, maybe all the sports globally. But I think it was just this innate need that he could not separate from and that was manifested in this relentless pursuit for winning that existed every single day. And that's not an exaggeration. Everything was centered around winning that day, and then winning the next day and then winning the next day.

Do you see a parallel between him and Jordan? And I ask that question, because the depiction of both of those legends in these latest documentaries is not always flattering. They have to give up a lot to have that single mind that that mindset about winning.

Yeah, I mean, I think they're one in the same. They just played different sports and one is a little bit older than the other. And a lot of sacrifice is necessary to achieve that level of success. You don’t just roll out of bed and win six NBA titles or win five World Series. There are a lot of things that you have to give up. And there are a lot of things that you have to give up behind the scenes where people don't see it. So I think in order to have great success that requires great sacrifice. And I think that that's true for any industry that anyone works in. If you have desires of being great, there's a great requirement that comes along with that. And I think that what makes Jordan and Jeter unique is that they accepted that responsibility and embraced it and took on the challenge. I think a lot of people are looking for the moment where things become easy, and it feels like they embraced the hard things into they became easy, and then went on to the next hard thing. And I think that that's like a major difference in who they are as athletes compared to a lot of other professional athletes.

Do you see anyone in the game today who has taken on Jeter’s mantle since his retirement? Not just on the Yankees, but sport-wide?

No, no. And I don't I don't mean that because I'm just the director of this film. But no, I mean, I think there are a lot of great players. I think there were a lot of great competitors. But there just aren't a lot of guys that have won multiple rings, let alone one. So I don't I don't think that we've seen a Jeter yet.

Let's talk for a minute about Alex Rodriguez. He factors heavily into this film. And for people who might not remember all the details, you know, he had been very close friends with Jeter when they came up. They had a falling out that lasted over a period of years. But then they ended up as teammates for many years. What did you learn about the Arod-Jeter dynamic by taking this project on?

I think there were young successful guys that were part of the public and there are a lot of pitfalls that come along with it. And I think that it can complicate relationships. And I don't think that it was entirely Derek's fault. I don't think it was entirely Alex's fault. But I think when you're younger successful people, there are entities and people out there that are trying to take advantage of what you have. And sometimes the cost of that is a friendship. And I don't think everybody at the time is as savvy or excuse me was as savvy as Derek was with the media. And I think that there are opportunities there for others to exploit. And then I think that it leads to personal friction, and it leads to the degradation of relationships and friendships. So I think some of it was just being innocent and naive, and not really understanding how the game works. And some of it was, you know, the ego, I think on Alex's part at the time, and I think a desire to be like Derek, and I think with Derek, it's, you know, having a small circle of trust and a very defined line on what and who he considers a friend. And when that's violated, you know, then he's very decisive and moving on from that person. Derek says this himself: you know, he considers it a character flaw to a certain degree. So I think everybody in some ways contributed to it just with the way that their life perspective and what's important to them, their values, their morals, what their priorities are. And then also this entity, the media, kind of being around and there's a there's a way to handle the media, and there's a way not to handle the media, and I think all of those ingredients can lead to a disastrous recipe.

What's your sense of what Jeter will do next? Obviously, his playing career is behind him. His years in the Marlins front office are behind him. But he does not seem like the kind of person who is going to sit on the beach.

Yeah, no, I think he has business ventures that he's going to pursue now. He hasn't told me this so this is just conjecture on my part, but I don't think that he's done with his dream of owning a major league baseball team. I think that at some point he's going to try to get back into that game. Now again, he hasn't told me this. There were no hints, I just feel like there's unfinished business after the Marlins situation and I know that this dream of his, we all know that it was a dream of his, he made that very clear for a long time. But I think that he's going to try to own a baseball team again. And I wouldn’t doubt him. I think he'll figure out a way to make that happen. That's my guess that eventually he'll win with another baseball team as controlling owner of that franchise.

So just one more thing. Your film makes clear how vital it is to win when you have the chance to win in baseball. The Yankees in ’96, Jeter’s first year, began a dynasty but then the revamped crew with many free agents in 2009 finally got the job done after years of first-round exits, and that was validating for many of those players. As you watch this current Yankees team play about .700 baseball right now, how important do you think it is for them to actually go all the way this year?

It's critical. I mean, I think that this year in particular, for this Judge-era Yankees, they need to win a championship and I know that that might sound a little extreme, but this is New York. I mean, that's how we think, that's how the franchise thinks. I think that they have to win a championship. It's a defining season for them, and how people will look back at this run under Judge, especially if Judge moves on to another team in free agency. I think it's absolutely crucial that they win a World Series. I try not to mince words about and I know that's like every Yankees fan wants them to win every year. But I think that the way they've been playing the expectations have increased even more. But I think Judge needs a championship in pinstripes. I think Brian Cashman needs one. Just given the recent run, I think Aaron Boone needs one. I just think the major players in this situation need a championship for a lot of different reasons.

Do you think Judge will be back?

I do. I think that the Yankees made this more difficult for themselves when they really didn't have to. I totally respect and support Judge taking that bet and cashing it in and having the best season of his career so far. But I think that they need each other in a lot of ways. I don't think that this is a Robinson Cano situation. So I think they'll figure out a way to come together, but I think the Yankees made it much more difficult for themselves. Do you think they're coming back?

I think they're both too big to fail. I mean, it just doesn't make sense for Judge to go anywhere else.

I agree.

And the Yankees can pay him whatever he wants. So they should.

Yeah, I'm in total agreement. We're in alignment there.

OK, one last thing. Can the Yankees beat Houston in the playoffs?

Oh, yeah, absolutely. Yes.

Randy, I love your confidence.

I know that they’re the boogeyman. But I mean, if you look at Yankees teams in the past, I mean, they're like the Angels. They're like Cleveland. We've seen this before. So yeah, so I feel confident they can win it.

Well, Randy, you're one of my favorite Twitter follows during a Yankee game, and I appreciate that. But more than that, I really love the ‘The Captain.’ Thank you for making it and thank you for sharing it.

Thank you for having me. And thank you for watching. I greatly appreciate it. I hope everyone enjoys it.

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A lifelong resident of the Capital Region, Ian joined WAMC in late 2008 and became news director in 2013. He began working on Morning Edition and has produced The Capitol Connection, Congressional Corner, and several other WAMC programs. Ian can also be heard as the host of the WAMC News Podcast and on The Roundtable and various newscasts. Ian holds a BA in English and journalism and an MA in English, both from the University at Albany, where he has taught journalism since 2013.
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