Charming, engaging, intense – ‘The Captain’ director Randy Wilkins on working with Derek Jeter

Two years ago, Spike Lee called Randy Wilkins and asked him who his favorite Yankee was. For Wilkins, a 42-year-old lifelong Bronx-born Yankees fan, the answer was simple: Derek Jeter. But Wilkins was confused. His mentor had called him out of the blue in the middle of the week with a seemingly random question.

It was then that Lee dropped the news: Wilkins’ favorite Yankee was filming a documentary series chronicling his life and career in the Hall of Fame. Lee and Jeter worked together on the project, and the legendary filmmaker wanted Wilkins to direct. Wilkins, who has won three Emmy Awards, previously directed the ESPN 30 for 30 documentary “86-32,” which chronicled the light middleweight boxing gold medal match between Roy Jones Jr. and Park Si-Hun at the 1988 Summer Olympics.

A few weeks later, Wilkins joined Jeter on a Zoom call and the project was up and running.

“In that moment, it changed my career,” says Wilkins.

The first episode of “The Captain” premiered on July 18 after the Home Run Derby, and new episodes of the seven-part series will air every Thursday through August 11 on ESPN.

ESPN spoke to Wilkins about the creative process behind The Captain and his experience working with a notoriously private sports icon.

ESPN: Derek Jeter has been incredibly private throughout his career. How did you prepare to do a documentary series about a person who doesn’t like to reveal much about himself?

Wilkins: He told me several times that he was willing to talk about things and that he was comfortable sharing things with the world. He mentioned that he wanted something that would be a record for his daughters because they weren’t around when he had that playing career. And then he started sharing things with me that I didn’t know. He told me experiences, moments, both personal and professional. That gave me the confidence that we could do it money.

I knew the outside world had many opinions as to what that would be or how that would be, but being near him and talking to him gave me all the confidence in the world that we would be able to to break this perception.

ESPN: As a storyteller, how did you balance the public perception of a person, how someone talks about who they are and who they actually are as a person?

Wilkins: We leaned into the perceptions and tried to challenge and break them. Some people walk away from it and consider it noise. I considered it one of the signposts to tell the story. It’s like, that’s what people think. I know from conversations with him that it’s not entirely true. Let’s get into that. Let’s talk about some things that break that perception.

I think we didn’t just do it for the story. We don’t do it just to break perceptions. We want to tell his story. I think part of his story struggles against those perceptions. There was an opportunity here to really surprise and excite people because they already have a certain thought about Derek.

ESPN: Was there anything that surprised you coming out of the process of making and reporting this documentary that you didn’t expect?

Wilkins: How intense Derek is. He’s one of the greatest competitors of all time. He’s on the level of Michael Jordan, Tiger Woods, Serena Williams. He’s just an incredibly intense guy when he needs to turn it on. That kind of presence is something that a lot of people don’t notice until they’re around him and start talking to him.

You see the smile, you see him joking around, you see him having fun and all that other stuff, but just below there is an edge that you can’t really see unless you’re around him. He’s charming, he’s engaging, but he’s really intense. That’s something I didn’t realize when I got into it, but it was very clear that it’s a strong part of his personality.

ESPN: What kind of advice did you get from Spike Lee throughout the project?

Wilkins: Just to do your thing He tagged me because he trusted me. I’ve been with him for almost 20 years, so he knows what I can do and what I’m capable of. I just shared the episodes with him and got minimal notes from him. He just said get on with your thing. He loved it. Spike knew he didn’t need to give me any hints and that I could navigate through here. I was his editor for a long time. Going to NYU film school was one film education, and then working for Spike for so many years was another film education. He knew that.

ESPN: How did you deal with the egos and intentions that people might have through a film like this, with so many overlapping storylines and there are so many big personalities?

Wilkins: You must demand that the people around you who have egos and intentions and intentions communicate honestly. It cannot be a one-way street where you are open and they are not. You must command respect when creating a two-way environment. You also need to understand people’s perspectives, that there are specific reasons why they look at things the way they do and in a certain mood.

This is real collaboration, where you respect other people’s perspectives and feelings and try to include them as much as possible, as long as it fits within the parameters of your own vision. I’ve never had a problem with collaborating, but I think there’s a limit. There’s a line that you as a filmmaker shouldn’t cross if you want to stay true to your story. You just have to make sure you are determined and vigilant to stick to that core vision. Charming, engaging, intense – ‘The Captain’ director Randy Wilkins on working with Derek Jeter

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