Captivating, Captivating, Intense – ‘The Captain’ Director Randy Wilkins in partnership with Derek Jeter
Two years ago, Spike Lee called Randy Wilkins and asked who his favorite Yankee was. For Wilkins, a 42-year-old Yankees fan born in the Bronx, the answer is easy: Derek Jeter. But Wilkins was confused. His mentor called him out of the blue in the middle of the week with a question that looked like a random question.
That’s when Lee dropped the news: Wilkins’ favorite Yankee was working on a documentary series chronicling the life and career of the Hall of Fame. Lee and Jeter collaborated on the project, and the legendary filmmaker wanted Wilkins to direct it. Wilkins, who has won three Emmy Awards, previously directed ESPN 30 for 30 “86-32” documentaries, documenting the light-weight gold-medal-winning boxing match between Roy Jones Jr and Park Si- Hun at the 1988 Summer Olympics.
A few weeks later, Wilkins started a Zoom call with Jeter and the project was done.
“It changed my career right at that moment,” Wilkins said.
The first episode of “Captain” premiered July 18 after the Derby Home Run, and new episodes of the seven-part series will air every Thursday on ESPN through August 11.
ESPN spoke with Wilkins about the creative process behind “The Captain” and his experience working with a notorious private sports icon.
ESPN: Derek Jeter has been extremely private throughout his career. How did you prepare to make a documentary about someone who doesn’t like to reveal much about himself?
Wilkins: He has told me many times that he is willing to talk about anything and that he feels comfortable sharing things with the world. He mentioned that he wanted something of a record for his daughters, because they weren’t around when he had this playing career. And then he started sharing with me things that I didn’t know. He told me experiences, moments, both personal and professional. It gives me all the confidence that we can do this money.
I know the outside world has a lot of opinions about what this will be or what this will look like, but being around him and talking to him, I have all the confidence to the world that We can overcome that perception.
ESPN: As a storyteller, have you balanced how the public perceives a person, how someone talks about who they are, and what kind of person they really are?
Wilkins: We relied on perceptions and tried to challenge and break them. Some people walk away and see it as noise. I see it as one of the guides to telling the story. It’s like, this is what people think. I knew from talking to him that it wasn’t entirely accurate. Let’s focus on that. Let’s talk about some of the things that disrupt that perception.
I think we didn’t do it purely for the story. We don’t do it to disrupt perception. We want to tell his story. I think part of his story is fighting against those perceptions. There’s an opportunity here to really surprise and engage people because they’ve got a specific mindset about Derek.
ESPN: Was there anything that surprised you during the shooting and narration of this documentary that you didn’t expect to be in?
Wilkins: How intense is Derek. He is one of the greatest opponents of all time. He’s on the level of Michael Jordan, Tiger Woods, Serena Williams. He’s just an insanely intense guy when he needs to turn it on. That presence is something a lot of people don’t realize until they’re around him and they start talking to him.
You see his smile, you see him joking around, you see him having fun and all this, but right underneath that is a side you really don’t recognize unless you’re around him. that. He’s charming, he’s attractive but he’s really intense. It was something I didn’t realize, but it was clearly part of his strong personality.
ESPN: What advice did you receive from Spike Lee during the project?
Wilkins: Just to go to your work. He tagged me because he believed in 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 episodes with him and received minimal notes from him. He just said keep doing your thing. He liked it. Spike knows he doesn’t need to give me hints and that I can navigate through this. I was his editor for a long time. Going to NYU film school was one film education program, and then working for Spike for many years was another film education program. He knows that.
ESPN: How do you manage the ego and agenda that people can have through a movie like this where so many plot lines intersect and there are so many big personalities?
Wilkins: You must ask the people around you to have ego and courage and the intention to communicate honestly. It cannot be a one-way street where you are open and they are not. You have to be respectful in creating an environment that goes both ways. You also have to understand people’s point of view, that there are specific reasons why they see things that way and in a particular frame of mind.
It’s true collaboration, where you respect the other’s point of view and feelings and try to incorporate them as much as you can as long as it fits within the parameters of your vision. I’ve never had a problem with collaboration, but I think there’s a limit. There’s a line you shouldn’t cross as a filmmaker if you want to stay true to your story. You just need to make sure that you are determined and prudent to stick to that core vision.
