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The Candid ‘Captain’: Director Randy Wilkins Peels Back the Curtain on Derek Jeter

The lifelong Yankees fan gives viewers an intimate look at the private-but-beloved Pinstripe icon in ESPN’s new seven-part Derek Jeter documentary The Captain.

There wasn’t much of anything do in the early months of the COVID-19 pandemic. By June 2020, we were already tired of staying at home, wearing masks when we went out, and being unable to catch a ballgame on a sunny afternoon. Heck, by that point, even The Last Dance had finished airing.

It was at that time when three-time Emmy Award-winning director Randy Wilkins got a call from a friend of his — a fellow director, in fact.

“I was just hiding out at home and Spike [Lee] called me and checked in on me to see how I was doing,” Wilkins told Boardroom. “And then he asked me who my favorite Yankee was, and I told him Derek Jeter, but I was a little confused because at that point, the Yankees weren’t playing. There were no sports really going on in America and I was completely thrown off by the question.”

Of course, Spike knew the answer to that question already, because the next thing he told Wilkins was that Jeter wanted to do a documentary on himself and the man behind She’s Gotta Have It and Do The Right Thing had recommended Wilkins as the director.

“I almost dropped the phone,” Wilkins said.

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The reason for his shock was twofold. There was the obvious amazement that he might be able to work with his favorite player on his favorite team, but there was also the same thought that probably would have run through any baseball fan’s head: Derek Jeter, the most reserved, private guy in baseball, wants to produce a project about himself?

The very premise felt odd, but as Wilkins soon learned, there is way more to Jeter than what the public has long perceived him to be. In fact, what became a seven-part documentary entitled The Captain shows Jeter in a light that no one outside of his inner circle has ever seen. He’s open, he’s candid… and he even swears a little.

The Captain debuts July 18 on ESPN immediately following the 2022 Home Run Derby at 10 p.m. ET. It will also be available on ESPN+.

RUSSELL STEINBERG: So you get the call from Spike and he says you have the opportunity to do this Derek Jeter documentary. What was your first thought about the kind of story you wanted to tell?

RANDY WILKINS: Well, I knew that I wanted it to be more than baseball. The intent of the film is to really reveal the man behind that pinstriped jersey, but also to place him in a much larger cultural context.

I think that Derek is one of those rare athletes that sits at the intersection of a lot of pieces of our culture, and I think that it was a really great opportunity to put that on display and tell a story where we’re obviously talking about Derek, but we’re also talking about ourselves. So the first thought that came to mind was making this a story that went beyond his sport, that went beyond his professional career, and I think in talking about him off the field, you were talking about all of us in some cultural context. So that was my instinct right from the jump.

RS: One thing that really surprised me in the first couple installments is how forthcoming he was, because it just didn’t seem to be who he was at all when he played. Did it surprise you to see him open up like that?

RW:  I was totally confident that that was how he was gonna approach this. He knew that to make this work, he was gonna have to open up and be candid and be honest. I think he wanted to do that. I think that was one of his intentions. So I wasn’t surprised. I knew what this was gonna be well before the world did, just because he made it clear that he wanted to be candid and it was my job to make him feel comfortable. We spoke about it and we made it clear on both sides that that was what we needed to make this work.

RS: I think it’s one thing to want to open up and and want to do something like this, but it’s another to be comfortable doing it. What sort of trust did you have to build with him?

RW: I think it was pretty significant to build that trust with Derek. I think trust and loyalty are one of the major tenets of how he looks at life and lets people into his circle and interacts with others. So trust was at the heart of everything. And I think I achieved that by just being myself. I wasn’t trying to get anything out of him. I wasn’t trying to take advantage of him. I wasn’t trying to use this for my own benefit. I wanted to genuinely tell his story and I was genuinely ecstatic to have that responsibility to do so.

I’m not starstruck, I don’t treat people with celebrity status any different than any other person that I come across. I am who I am and I’m very confident in that, and I’m comfortable with that, so I thin in being my authentic self, I earned Derek’s trust.

I was just there to help tell his story and to make this as great as it could possibly be, and I think it also helped that I’m a huge baseball fan. I’m a huge Yankees fan. I understood what went on in his career. I know the pressures that he faced because I was probably a part of that fan base that put pressure on him, so I just had a very intrinsic understanding of what he went through, at least from the outside, and I think that he knew that I was coming in with the right intentions and and not looking to take advantage of him.

RS: Once you actually peeled back the curtain, is there anything about his personality or about his career that really surprised you?

RW: Yeah. I mean, there are a couple things — I think his edge and intensity are things that people don’t really realize until you are actually around him. I think that when he played, he had that smile, he enjoyed playing the game, but underneath all of that was an extremely intense competitor. You feel that even when he’s talking about some of these baseball moments and the emotions that come along with him. You can feel the edge coming off of him immediately, and I think as a fan and as an observer of his career, you don’t really pick up on that intensity. He plays with such grace and was so smooth that you kind of take it for granted that he was this great competitor. So that’s one thing.

Another thing is just how much his biracial identity influenced the way that he interacted with the world and the way that the world interacted with him.

RS:  You started working on this right around the time The Last Dance finished airing. Michael Jordan and Derek Jeter are two very different people, but they both have that similar competitive edge to them. Did The Last Dance influence you at all in mapping this out?

RW: No, The Last Dance had nothing to do with what we were trying to do. I respect The Last Dance. I watched The Last Dance like everybody else, but this is a different story, different athlete. I think we had a different intention.

I think a lot of the things with The Last Dance centered around that amazing footage that they had and then kind of building the story around this incredible treasure trove of footage and experiences in the ’98 season. This film, The Captain, is telling a story about the man behind the pinstripes. There’s no hidden footage that nobody knew about with the Yankees. Really, this was about Derek the man as much as it was about Derek the baseball player.

Derek Jeter speaking to the crowd at Yankee Stadium as Michael Jordan looks on during “Derek Jeter Day” on Sept. 7, 2014 (Al Bello/Getty Images)

And I would say that Michael and Derek are actually more similar than people realize. I think Michael’s a little bit more outward with the public in terms of his competitiveness and trash talk and all that, but they’re close friends for a reason. They rely on each other for a reason, and I think that there are a lot of similarities between the two men that brought them together and built that friendship. So I wouldn’t say that they’re different; I think that they manifested in different ways, but in terms of who they are as people, I think they have a lot of values and commonalities among them.

RS: Something that Jeter talked about his entire career and is very apparent here, too, is the impact that his parents have had on his life. They’re very prominent in The Captain. What was it like working with them and getting to know them?

RW: It was just as much of an honor to speak and work with his parents and his sister, Sharlee, as it was working with Derek. He has, legitimately and genuinely, an amazing family. You see where Derek gets it from, you see where Sharlee gets it from — and I know people have said that before, but it’s sincerely true.

They’re incredibly tough, as an interracial couple in the ’70s, ’80s. For two people to join together in marriage at that time, meeting in Germany and then coming over here and facing all of these hardships, it really molds you, and I think it molded Derek’s character. And I think they created the foundation for who he is as a person and as a player.

L to R: Dr. Sanderson Charles Jeter, Dorothy Jeter, Derek Jeter, and Sharlee Jeter attend the 2009 Sports Illustrated Sportsman of the Year Celebration (Andrew H. Walker/Getty Images)

RS: When you think about the entire process, what was the biggest obstacle you faced? What was the toughest part?

RW: The toughest part was just mining all the footage and making sure that we made good choices and that we made choices that people will connect with emotionally. We did a lot of preparation before we filmed our first frame. I think the biggest thing really was just making the right choices so that people were always engaged and that people always felt like we were moving forward and that they were learning more about Derek and the Yankees and MLB.

I think that the toughest thing was just making sure that emotionally we were keeping that energy so people who are Yankees fans, not Yankees fans, baseball fans, not baseball fans found something that they can engage with throughout the entire ride. ‘Cause you know, seven hours is a long time, and people are sacrificing their time to engage with you, so we just wanted to make sure we made the right choices to make it as engaging as possible.

RS: Seven hours is a long time, but that’s not very long if you’re trying to fit an entire career and everything that went into it. If you could zoom in and go deeper into one point in his career or his life, what would it be?

RW: Honestly, the celebrity and race episode. I’d like to go even deeper with it because I think that baseball stuff, you know, everybody can access it.

People have some semblance of what was going on on the baseball side, but I think the celebrity culture side, the pressures, the consequences that go along with it are things that, you can go on for a long time. I think you can expand it into even larger and deeper conversations. And certainly, when you speak about race in America, you can delve into that for much longer, both within Major League Baseball and outside of Major League Baseball. So I would say episode five is probably the one episode that could go much deeper if there was more time.

RS: You highlight the leadoff home run in the 2000 World Series, you have the flip play against the A’s, the dive into the stands in ’04, all those memorable plays. As a Yankees fan, what’s the quintessential Derek Jeter moment, to you?

RW: Whenever they won a World Series.

RS: That’s a very Jeter answer.

RW: Well, I mean, it’s true, though. That’s what this is all about, winning the championships. So, you know, five big moments, five rings, I would say that those were the quintessential Jeter moments.

The first episode of Randy Wilkins’ Derek Jeter documentary The Captain premieres on Monday, July 18 on ESPN following the 2022 Home Run Derby at approximately 10 p.m. ET. It will also be available for streaming on ESPN+.

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