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. “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

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_. WATCH ON DEADLINE 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.”