Derek Jeter is finally pulling back the curtain, inviting the world to examine the private life he so closely guarded during the two decades living his childhood dream as the Yankees’ shortstop.
With ESPN and ESPN+ set to begin airing a seven-part series, “The Captain,” viewers will have an opportunity to know Jeter like never before.
Directed by Randy Wilkins, the documentary uses in-depth interviews with Jeter, his family, former teammates and others to explore the universe around the Hall of Famer and five-time World Series champion.
“For the first time, really, I had a chance to reflect on my career,” Jeter said. “I sat down for over 30 hours talking about my career, from 1992 up until this past year. You never know if the time is right, but it seemed to me that I was ready to do it. I didn’t know what I was getting myself into, but I’m glad I did it.”
As we await the weekly installments of Jeter’s story, which will air each Thursday, here is a recommended syllabus to whet your appetite for a deeper investigation of his career and the events that made Jeter a fan favorite.
O’Connor’s New York Times bestseller draws upon unique access to Jeter and more than 200 new interviews to reveal how the biracial Jeter, New Jersey-born and raised in Michigan, became New York’s most beloved sports figure and the face of the steroid-free athlete.
Over 448 pages, O’Connor deftly digs into Jeter’s early struggles in the Minors, when homesickness and errors threatened his career, to the brightest nights in the Bronx and his publicized battles with “frenemy” Alex Rodríguez. Arguably the most complete print synopsis of Jeter’s career, O’Connor’s reporting provides glimpses of the layers that simmered under Jeter’s placid demeanor.
The snapshot remains frozen in time, Jeter leaping beyond first base, his fists raised toward the evening sky. The captain walked off a winner in his final at-bat wearing the fabled pinstripes, a moment that could not have been better scripted if it had been shipped directly from Hollywood.
Jeter’s final Bronx hit did not come in a World Series game or even one that mattered in the standings — the opposite-field single off the Orioles’ Evan Meek ended the only Yankee Stadium game that Jeter ever played with his team mathematically eliminated from the postseason contention. But no one in the building that night would have dared call it a meaningless game.
To appreciate how prevalent Jeter had become in the public consciousness by the turn of the millennium, watch his turn in the fabled Studio 8H of New York’s Rockefeller Center, when he joined a star-studded SNL cast and offered a solid performance as the seventh host of Season 27.
Jeter’s hosting chance came in the heart of a city still wounded by the events of Sept. 11, 2001 — the title cards showed Jeter in full pinstriped uniform, posing in front of a digitally inserted stars-and-stripes flag — and shortly after the Yanks were upset by the D-backs in an emotionally charged World Series.
Yet Jeter showed that he was game to laugh, even appearing on the episode’s segment of Weekend Update to tackle the important point/counterpoint topic of “Derek Jeter Sucks” with Red Sox fan Seth Meyers.
Long before Jeter’s arrival, “The Boss” knew a thing or two about turning controversy into an entertaining television commercial. Steinbrenner’s exceedingly public spats with manager Billy Martin helped produce an iconic early 1980s TV commercial for Miller Lite beer — “Tastes great! Less filling! You’re fired!”
Jeter and “The Boss” re-visited that playbook in 2003, after Steinbrenner had lambasted his shortstop for attending a late-night birthday party during the 2002 season. With a wink to the headlines, Steinbrenner called Jeter into his office, asking, “How can you possibly afford to spend two nights dancing, two nights eating out and three nights just carousing with your friends?” Jeter responds by flashing his credit card.
The acting is fine, but Steinbrenner’s rump-shaking appearance in a conga line steals the 30-second clip.
Yankeeography by YES Network
With 24 hours of programming to fill each day, one of the YES Network’s first projects in 2002 was to dig deep into the archives, commissioning a series of Yankeeography episodes. They would tell the background stories of the most important names in Yankees history, drawing upon archival footage and fresh interviews from the clubhouse and field.
Volume 1 was a veritable who’s-who of legends destined for Monument Park: Jeter, Thurman Munson, Babe Ruth, Ron Guidry, Don Mattingly and Joe Torre. YES has periodically updated Jeter’s episode over the years, and it remains in regular rotation on the cable network.
Yes, we wrote this book! Without the championships, Jeter’s story would not have been quite as compelling — his goal each year was to raise the World Series trophy, deeming any season in which the Yanks weren’t the last team standing as a “failure.” The 2009 season was the fifth and final time Jeter would deliver, a fact not fully appreciated in the moment.
Our 2019 project was to re-assemble the “Core Four” and figuratively re-open the new Yankee Stadium a decade later, interviewing as many people as possible who had been connected to the club. Since Jeter and others had retired by then, we uncovered many fresh details and never-before-heard anecdotes from an unforgettable season.