ESPN’s ‘The Captain’: Director Randy Wilkins On Getting Spike Lee’s Blessing To Tell The Story Of New York Yankees Great Derek Jeter

Dade Hayes
·8-min read

Randy Wilkins connects with Derek Jeter, subject of his seven-part ESPN documentary series, The Captain, on a few levels.

For starters, Wilkins is a lifelong New York Yankees fan, and Jeter was the linchpin of five World Series championships captured by the team between 1996 and 2009. In his filmmaking career, Wilkins also can relate. While he wasn’t a teen-ager like Jeter when he got his big break, getting the chance to tell the story of his hero resulted from a surprise endorsement from Spike Lee, who is an executive producer of the series.

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“In June 2020, he called me to check up on me,” Wilkins recalled in an interview. “He asked me who my favorite Yankee was, just out of the blue. I said, ‘Well, Derek Jeter.’ I was very confused as to why he was asking me that. And the next thing he said was, ‘Derek Jeter wants to do a documentary and I’m putting you up to direct it.’ I almost dropped the phone.”

While Jeter had wanted Lee to direct, the filmmaker was juggling a few other projects, so he decided to steer Jeter to his protégé, who had once been his film student at NYU before going on to climb the ladder in the editorial department of several Lee projects. Most recently, he was an editor of the Netflix series She’s Gotta Have It and director of the premiere episode of Dear … for Apple TV+, which focused on the impact of Lee’s 1987 film School Daze.

ESPN, via its flagship 30 for 30 franchise, has specialized in in-depth portraits of athletes, with the bar being set by 2020’s The Last Dance, the story of Michael Jordan’s final season in the NBA. Jeter has been an early advocate of telling stories from athletes’ perspective, having founded The Players’ Tribune in 2014. The media outlet has since broadened its scope and came aboard as one of the producers of The Captain.

The series will premiere Monday night at 10 p.m. ET, both on linear ESPN and streaming on ESPN+, with the second episode following on Thursday. Pairs of episodes will air and stream on July 28 and August 4, with the finale set for August 11.

Using Jeter’s farewell season in 2014 as a through-line, the series charts Jeter’s rise from a Yankee-loving toddler to a high school standout in Michigan who was drafted by his favorite team in 1992. Through interviews with Jeter, mother and father Dorothy and Dr. Charles Jeter, sister Sharlee Jeter his wife, the show explores Jeter’s unique drive, and his exploits once he became the Yankees’ full-time shortstop in 1996.

Even the mildly baseball-curious will feast on interviews with Roger Clemens, Tino Martinez, Andy Pettitte, Jorge Posada, Willie Randolph, Mariano Rivera, Alex Rodriguez, CC Sabathia, Darryl Strawberry, Joe Torre and Bernie Williams. Cultural figures like late-night TV hosts Desus & Mero and hip-hop artists Fat Joe and Jadakiss also appear, as does Jeter’s wife, Hannah.

Rodriguez was a surprise get, Wilkins said, given his complicated history with Jeter. The two became friends in high school and wound up in the media spotlight for years given they both played shortstop and were seen as the future of the sport. Subsequent betrayals of Jeter (conceded on camera by Rodriguez) and his decision to move to third base when he was signed by the Yankees provide lively material. While the pair played on one World Series winner in 2009, the impression was left that it should have been more, given the team has won more than any other team in baseball. This year’s Yankee team has a good chance to end the 13-year title drought, having compiled the best record in baseball through the All-Star break.

The climactic seventh episode focuses on Jeter’s bumpy period as CEO of the Miami Marlins and decision to step away from the team earlier this year after four-plus years of mostly frustration.

The Marlins-centric episode expanded upon the original plan to make an even half-dozen, Wilkins said, when filmmakers sensed the makings for a timelier finale. “We definitely mapped everything out, but we allowed ourselves the opportunity to go in different directions if that’s where the story went,” he said. “My philosophy is, footage is queen. If that’s where it’s leading us, that’s where we’re going to go. … The emotional beats that were arising out of the footage was essentially the road map to follow.”

Unlike The Last Dance, The Captain doesn’t center on never-before-seen archival material, but its canny revisiting of past clips bears considerable fruit. One example is the iconic flip play in the 2001 playoffs, when Jeter took a throw from right field on the dead run and flipped it to Yankees catcher Jorge Posada in time to tag out the Oakland A’s runner trying to score. The play came as the Yankees were rallying New York and the country at large just a few weeks after the September 11 terrorist attacks.

Wilkins said his goal with sequences like the one documenting the flip play was “creating that larger context in which that play exists. Sometimes, they just show you the play and they’re talking about the brilliance of the play, but the context that the play lives within is just as important. What makes that scene work is there’s so much emotional investment with the team, with where the country was at the time, where the city was at the time. It was this moment that transcended baseball, it was this survival moment where the city and the country was going through.”

While Lee is known for often appearing on TV as an unabashed booster of the Yankees as well as his beloved Knicks, Wilkins said he consciously wanted to avoid indulging his fan side as he told the story. “I had a very clear intent to make sure that this was accessible to everyone – Yankees fans, non-Yankees fans, baseball fans, non-baseball fans,” he said. “My fandom has nothing to do with my filmmaking. They’re two separate things. I think my fandom helped me understand what the story was and who he is. But the intention was to go beyond that. … The intention was not to make Yankees fans happy. … We wanted to humanize Derek to a wide-ranging audience.”

One of the most compelling aspects of the first five episodes, which were made available to press in advance of the show’s premiere, is the treatment of Jeter’s race. Born to a Black father and white mother, Jeter was brought up to be prepared for society to automatically categorize him as Black. The Captain also explores the knock on Jeter for not always seeming to comport to certain definitions of Black-ness and also for not speaking up publicly about racial episodes in New York or in the country. One remarkable passage in Episode 5 features one sportswriter matter-of-factly observing that Jeter always struck him and the press corps at large as “almost colorless, not only physically but in the way he spoke.” Because Jeter had “set the ground rules” with the media, reporters generally didn’t bother asking the star about controversial issues touching on race.

When those comments are repeated to Jeter and his family on camera, their disdain is palpable. (“Who the f–k are you?!” the former Yankee responds. He and other interviewees also  note the dilemma facing high-profile athletes (Jordan and Tiger Woods among them) in terms of weighing in on topical societal issues. Former Yankee great Reggie Jackson says at one point that he needed to reach age 75 before feeling comfortable publicly addressing race.

“I don’t really have a takeaway for the audience,” Wilkins said. “I just wanted to tell a well-rounded story about who Derek Jeter is and his identity as a biracial Black man is a huge influence on the way he views the world. It’s a huge influence on the way that he performs as a baseball player, on the way he engaged the public and people in private. It’s just a considerable part of who he is.”

He added, “I believe telling the story of Derek Jeter is also telling a story about ourselves, to a certain degree. How we treat others, how we perceive others, how we interact with others, based on multiple factors. There is a lot going on with Derek Jeter in a racial context that a lot of people want to run away from and pretend that it’s not there. I wanted to put the microscope on it and force people to confront it.”

With his playing career nearly a decade in the rear-view mirror, “he in some ways is a better position to talk about it because there aren’t immediate ramifications for him,” Wilkins said. “He’s almost protected by retirement now, which says a lot about the system around him, not necessarily him.”

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