You can’t mention Yankee greats like Babe Ruth, Joe DiMaggio, Mickey Mantle, and Reggie Jackson without saying the name of Derek Jeter. The kid from Pequannock Township, New Jersey, would later fulfill his lifelong dream, anchoring multiple championship teams in the late 1990s-early 2000s dynasty years. Jeter had an undying tenacity to win — instilled in him at an early age by his mother, Dorothy, and father, Sanderson Charles Jeter. It takes someone of astute and unfazed demeanor to play in a city like New York. If the bright lights and nightlife don’t get you, the aggressiveness of the media might. Jeter handled his career like a dedicated, consummate professional focused on the goal of winning championships. Given that stance, the legendary shortstop kept aspects such as his personal life to the wayside. Tight-knit friends, teammates, and family surrounded him, and Jeter was determined to keep it that way.

Director Randy Wilkins, a lifelong New York Yankees fan, was tasked to break through that shell in a seven-part documentary from ESPN named The Captain. When executive producer Spike Lee asked him to helm the project, Wilkins could have elected to provide the audience with hours of hero worship. Instead, The Captain displays the highs and the lows of Jeter’s career, personal triumphs and difficulties, and the city he called home. We spoke to Wilkins about untangling the mysticism behind Jeter’s relationship with the Yankees, how important it was to show his background, and why his competitiveness still burns as bright as ever.

Substream: When I watched episodes of The Captain, it felt great to relive all the footage and stories of the Yankees dynasty. Another thing I noticed is the story is made accessible for people who aren’t baseball fans to get it. Derek Jeter is a notable name that transcends sports, but his competitive fire still burns bright. Was it important to you to balance those perspectives?

Yeah, it was crucial. We went into this wanting the film to be global and universal  — not just for Yankees fans or baseball fans. We wanted to be fully understood that Derek transcended the sport. He was not just a Yankee. People who didn’t follow the Yankees or do follow-up baseball still recognize his name. I think we had to show that audience as much respect as the Yankee fan audience.

So, we needed to strike that balance. I wanted to ensure that people who might not have experienced those years — whether they weren’t fans or were too young — could engage with the story just as much as a Yankees fan. I think we did that and people will enjoy it.

I remember, when I was younger, seeing Derek as a rookie and growing into being a Yankee great. There always felt like he had a business-like approach to everything. It created a bit of a distance where now athletes are expected to be open. The media barely covered Derek’s bi-racial background. How was it for you to have a subject like Derek, who meticulously decides what we see, be vulnerable for this documentary?

Your use of the word vulnerable is very accurate and pressing. That was the one word I always went back to when I was conceiving this project. It was crucial that Derek was candid, honest, but also vulnerable. For any project that I make, I think that’s like crucial. I believe in emotional storytelling and making emotional connections between the subject, what we see on the screen and the audience.

One of my intentions was to ensure that we showed Derek wasn’t this perfect guy or a player. He’s an icon and a legend, but there was a long, winding road to help them get to that point — both on and off the field. You mentioned 56 errors and the struggles that he had. Those struggles extended into his personal life as a biracial black man. How the world treated him when he was with his parents and his sister influenced him. Mainly how he viewed the world and how he went about his business as a baseball player.

That’s important, too, to highlight. I think that even when he was a Yankee, there were a lot of disappointments in his mind. There are more failures than successes because he only has five rings. So, in his mind, there could have been more. We approached this with a balanced view that not just celebrated its triumphs or went down memory lane of those trials. The documentary also gives as much time and care about the failures and obstacles you face. I think that all those things contributed to who Derek Jeter is.

During his early playing days, the “big three” of American League shortstops were Derek, Nomar Garciaparra, and Alex Rodriguez. The Captain dives into the highs and lows of Derek and Alex’s friendship. There was a friendly rivalry during the New York/Seattle days, some interviews that rubbed Derek the wrong way, and tensions when Alex was traded to the Yankees in 2004. I like The Captain provides them both the space to talk about that time in total. 

I mean, it’s a great dramatic character arc, right? You have this great friendship that brings these two incredibly talented young men together. They share the same passion, both excelling at it, and then there’s a bit of downfall and conflict. It’s a traditional storytelling arc, and I think that was the appropriate way to handle it. There’s a lot of complexity in the relationship and nuances in how things played out.

We had to respect that and capture that. I don’t think just having one scene that says, “yeah, they didn’t get along, or they had some issue,” would do it justice. It would be disrespectful to Derek and Alex because a lot more went into it. A part of it was Derek was the rare young star who was more mature beyond his years. I don’t say that as a criticism of Alex. Having that mature perspective is tough if you’re 21 and on top of the world. Derek was rare in that instance.

Playing in New York and Derek understanding how media works, and Alex being in Seattle and not having that pressure of media demand also has something to do with it. I think Alex wanted a bit of what Derek had — team success. Alex is one of the greatest players of all time, but wasn’t able to win as much as Derek. I think that all great competitors view and measure themselves in that way. So in the film, we wanted to capture all of that and didn’t want to sensationalize it. It’s a human relationship story. We tried to treat that with care and build the story up.

As much as The Captain is a story about Derek Jeter’s life until now — it’s also a New York story. The music, clubs, and culture are just as crucial to every installment as is the baseball aspect.

Intertwining the New York aspect of Derek’s story is natural. His mom’s family is from New Jersey, so the northeast is in his blood. I know he grew up in Kalamazoo, but part of his heritage is rooted in New Jersey, right across from the stadium. The time he played was a crucial era in New York City. You had 9-11, the Giuliani years, and how the city evolved while he played with the Yankees. I think he’s very much an encapsulation of where New York was at that time.

It was important to make sure it was a part of the film. Derek, he’s Michael Jordan and Tiger Woods in terms of that level of competitive desire. That was one thing that stood out to me immediately when I spoke with him — this intense competitiveness. I mean, he has an incredible edge like that. When he’s talking about competition, it just clicks in. He can’t remove himself from it or try to hide it. He’s on the level of MJ and Tiger in that competitive spirit. Derek sees everything through the prism of winning and expects nothing less.

In looking back on Derek’s relationship with the Yankees, there might be a rosier picture in the minds of many. The documentary explores his tensions with General Manager Brian Cashman and the late George Steinbrenner. Was it essential for you to show despite the dream coming true, the MLB is still a business?

A big thing going into this was trying to demystify the romanticism connected to the relationship with Derek and the Yankees. People gloss that there was tension and conflict. It wasn’t this magical ride the entire time. I know the prevailing notion is Derek always wanted to be a Yankee and live his dream. That was true, but Major League Baseball has a business side. There is an infrastructure in place where players are continuously evaluated, and a lot of money is involved. Teams and organizations want to ensure they’re spending their money wisely.

If they can save a couple of pennies, they’re going to save a couple of pennies like any other big organization. We wanted to peel the curtain back a bit and say, “look, it wasn’t sweet the entire tie. It wasn’t a perfect 20-year situation.” I think that’s also part of both Derek and the Yankees story. Sometimes business comes before baseball and winning. You have to manage those things, and it could lead to conflict. We wanted to make sure that in telling a balanced, well-rounded story, that didn’t come across like one big fairy tale.

Photo Credit: ESPN Films