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Derek Jeter doc The Captain
Image: ESPN

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Derek Jeter Documentary The Captain is a Worthwhile Watch, but It’s No Last Dance

The Captain Review

The success of The Last Dance, two years ago, indicated that we were about to get a series of subsequent, multi-part, career-spanning documentary series about other athletic greats, almost always produced with the cooperation of the subjects themselves. 

We’ve already gotten the Tom Brady version, as well as Magic Johnson’s, and the latest is The Captain, a seven-part documentary about the life and career of retired New York Yankees superstar and Baseball Hall of Famer Derek Jeter. 

While Jeter, like Jordan, is an all-time great who won lots of championships and was a recognizable media figure. However,  there were reasons to be skeptical about the project, starting with a big one: Jeter isn’t particularly known for saying interesting things. 

Jeter was a consistently great player who was never particularly controversial and remained in the good graces of the media for the vast majority of his two decades in New York, despite playing in the nation’s toughest media market.

Derek Jeter doc The Captain
Image: ESPN

Of course, it must have helped that Jeter, while never especially rude or adversarial to the media, went his entire 20-year playing career without ever saying a single interesting or memorable thing. Sure, there was a lot of attention on his dating life, but Jeter was never really painted as sleazy or lecherous, aside from that whole rumor about the gift baskets to ladies who visited his apartment (denied, vociferously, by Jeter in the documentary.) 

The documentary also, like The Last Dance and most other major sports documentary series of the past five years, was produced with input from Jeter’s own production company, so it should be seen as his side of the story. Jeter’s The Players’ Tribune and his longtime agent Casey Close produced the series, along with ESPN Films, 30 for 30 veterans Connor Schell and Michael Tollin, and Spike Lee; Lee protege Randy Wilkins is the director of all seven episodes. The film is not part of the 30 for 30 series. 

What we get with The Captain is an entertaining rampage through about 25 years of baseball history, centered on Jeter and the Yankees, with smartly-assembled historical footage, well-chosen talking heads, and Jeter himself sharing much more than he typically does.  There’s a great deal of nostalgia value here, and we get a few revelations, mostly about Jeter sharing how he really felt at various times. But overall, for many reasons, The Captain is nowhere close to the achievement The Last Dance was. 

The documentary uses a half-hearted framing device, at Jeter’s final home game in 2014. The seven episodes go through different eras of Jeter’s career: The first is about his childhood and early life, and the second is about his arrival with the Yankees and early struggles. The third follows the Yankees’ dynasty, in which they won four championships in five years between 1996 and 2000. 

Derek Jeter doc The Captain
Image: ESPN

The fourth episode is about the 9/11 attacks, leading into Jeter’s “Mr. November” home run in a losing effort in the 2001 World Series, and then the Yankees’ 7-game ALCS wars with the Boston Red Sox in 2003 and 2004. Episode 5 goes into the aftermath of that 2004 loss, followed by the controversy when teammate Gary Sheffield made comments about Jeter being “not all the way Black.” 

The series wraps up with the 2009 World Series win, Jeter’s 3000th hit, the end of his playing career, and his post-retirement marriage, while the finale covers Jeter’s becoming a father, his Hall of Fame induction, and his ill-fated tenure as CEO of the Miami Marlins. 

The Captain is by no means a colorless or boring story, but a lot of the elements that made The Last Dance special aren’t really present in Jeter’s story. He didn’t really have high-profile, bitter rivalries with teammates or opponents, and he got involved with major controversies very rarely. 

And a lot of the controversies laid out here are nothing burgers, like when George Steinbrenner got mad at Jeter for supposedly partying too much, or when Jeter and the Yankees had a tense late-career contract negotiation that ended up getting resolved amicably. It’s all the kind of stuff that really intrigued the New York tabloids at the time, but isn’t really worth remarking on, 20 years after the fact. 

Throughout, the alternating friendship and rivalry between Jeter and Alex Rodriguez is something of a through-line, as the two came up together as young shortstops (along with the largely forgotten Nomar Garciaparra), got into early disagreements, were on opposite sides of the Yankees/Red Sox wars, and ended up as teammates. It was, however, more of a 20-year, love-and-hate cold war than the open hostility that existed between, say, Michael Jordan and Isiah Thomas, and the two are set to team up this week to host a Manningcast-style baseball broadcast this week. 

Derek Jeter doc The Captain
Image: ESPN

There’s also a long section in the fifth episode laying out why, much like Jordan, Jeter never spoke up about any political issues during the entirety of his career, a section marked by pontification by veteran sportswriter Wallace Matthews that Jeter does not “identify racially,” which is met by uncharacteristic but deserved expletives from the captain himself. 

The film does a good job collecting most of the relevant Yankee teammates and opponents, with exception of the ones accused of sex crimes (John Wetteland, Chad Curtis) and domestic violence (Chuck Knoblauch.) A segment in the third episode details the episode when Curtis ripped Jeter for fraternizing with an opponent, Rodriguez, during a brawl; Curtis isn’t offered the chance to defend himself, likely because, at the time of filming, he was finishing up his 7-year prison stretch for sexually assaulting three underage girls. 

Also interviewed are Yankees owner Hal Steinbrenner, — who sounds way more like Larry David’s old impression of his father than George Steinbrenner ever did — about a dozen New York sportswriters, and a pre-breakup Desus and Mero. As for semi-canceled 1990s pitchers whose misdeeds have kept them from the Hall of Fame, Roger Clemens is interviewed in the film, but Curt Schilling is not. 

Those who were baseball fans during the 1990s and 2000s, whether they loved or hate the Yankees, are bound to love The Captain, and the film shows a more interesting picture of Derek Jeter, the man, than what we saw for all those years. But what The Captain doesn’t do is reinvent the documentary form in any appreciable way. 

Written By

Stephen Silver is a journalist and film critic based in the Philadelphia area. He is the co-founder of the Philadelphia Film Critics Circle and a Rotten Tomatoes-listed critic since 2008, and his work has appeared in New York Press, Philly Voice, The Jewish Telegraphic Agency, Tablet, The Times of Israel, and RogerEbert.com. In 2009, he became the first American journalist to interview both a sitting FCC chairman and a sitting host of "Jeopardy" on the same day.

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