ESPN’s Derek Jeter Docuseries ‘The Captain’ Is a Walk-Off Home Run of Nostalgia and Intrigue

It’s difficult to quantify the greatness of Derek Jeter, but the word often used to explain his indelible impact on the game of baseball is “intangibles.” The difference between exceptional and legendary is an ineffable elixir that can’t completely be measured by wins and losses. New York’s immense affinity for Jeter, a five-time World Series champion who was elected to the Hall of Fame in 2020, isn’t merely based on box score dominance, but for an emblematic ideal of how the game of baseball is supposed to be played.

Most careers are defined by stats, but Derek Jeter’s career is remembered by moments. “The Flip” in the 2001 ALDS, “the Dive” in a 2004 regular season game against the Red Sox, baseball’s iconography is forever linked to the Yankees shortstop. In 2020, sports fans were treated to the Michael Jordan docuseries The Last Dance. Now it’s Mr. November’s turn.

Debuting Monday, July 18 on ESPN and ESPN+, The Captain is an expansive look at the life and career of the famed Yankee great. Directed by Randy Wilkins, the seven-episode series (with each installment lasting about 50 minutes) features surprisingly candid interviews with Jeter and a host of his family members and former teammates, including Roger Clemens, Andy Pettitte, Jorge Posada, Mariano Rivera, Darryl Strawberry, and, yes, Alex Rodriguez. The Captain is a mix of personal and professional, covering New York’s dynastic run in intricate detail while also exploring race, celebrity culture, and Jeter’s complicated relationship with the media. The historically guarded Jeter is uncharacteristically forthright as the docuseries seamlessly blends fascinating baseball anecdotes (Rivera almost being traded, Derek’s thoughts on the historic Yanks/Sox rivalry) with the messy, messy drama that accompanies being a marquee athlete in New York City.

There’s no shortage of buzzy moments from the first five episodes, with the inclusion of the infamous gift baskets urban legend (a longstanding rumor that Jeter used to give gift baskets to one-night stands) already making the rounds on social media. The story, which originated from a 2011 NY Post article, has endured for years. In Episode 5, Jeter vehemently denies the rumor (“never happened”) and shares an amusing tale about a random guy at Starbucks who told Jeter that he inspired him to start giving out his own gift baskets.

“I turned around and said, ‘Dude, you’re a fucking idiot,'” Jeter says with a laugh. “And the look on his face. Like, did he think I was gonna say, ‘Yeah, good job man’?”

The Captain also dives into Jeter’s complicated relationship with Alex Rodriguez, covers various dustups the shortstop had throughout his career with both management (Brian Cashman and George Steinbrenner) and teammates (David Wells and Chad Curtis), and, similar to The Last Dance, touches on his unquenchable thirst for excellence.

“The ultimate goal is to win,” Jeter says during the final moments of the fourth episode. “I wanted to beat you. And if you beat us, I had a problem with it. I had a real problem with it. It bothered me.”

The Captain is broad enough to entertain anyone, but it’s an absolute must-stream for baseball fans. With the All-Star break just around the corner, ESPN’s latest docuseries is the perfect way to fill that MLB-shaped hole in your streaming schedule.

The first episode of The Captain premieres Monday, July 18 on ESPN and ESPN+ at 10:00 p.m. ET (after the Home Run Derby).