ESPN Docuseries ‘The Captain’ Shows Derek Jeter’s Bumpy Road To Star Status

Chris JacobsJuly 22, 2022

For more than two decades in the 1990s and 2000s, Derek Jeter was a linchpin of the New York Yankees’ renaissance. Now, ESPN is giving his career the documentary treatment, examining the larger-than-life figure behind the Bronx Bombers’ resurgence with a seven-part series entitled “The Captain.”

During his 20-year career based in the country’s biggest media market, Jeter became a bona fide celebrity, not just in New York, but nationwide. “The Captain” explores some of these moments, including an infamous rumor about Jeter giving his dates “gift baskets” — an incident the star uses the documentary to refute publicly.

Jeter, like Yankee legend Joe DiMaggio before him, spent much of his career exuding effortless confidence on the field. But behind the suave appearances, the glitz, and the glamour came hours and hours of hard work to make the majors — not to mention the practice needed to keep one’s skills sharp. “The Captain” explores these under-examined sides of Jeter’s career, to study the individual behind the myth and fame and all the effort that went into making those seemingly effortless plays.

Competitive Desire

Two themes stand out during the series’ first episode, which focuses on Jeter’s youth and path to the majors. Born in northern New Jersey, Jeter spent most of his childhood growing up in Kalamazoo, Michigan, but return visits to his grandparents’ house every summer sparked a deep love of Yankee baseball and a desire to play for the team at shortstop.

Achieving that dream first required a level of competitiveness that Jeter received from his parents. Both Charles Jeter and his son recounted how the former wouldn’t let the latter win at anything — not even when watching “The Price Is Right” at home.

His mother made “can’t” a four-letter word in the Jeter household, but success required not just determination, but effort. Friends from Michigan recounted how Jeter would spend cold, snowy winters holed up in a makeshift batting cage, putting in the practice that would eventually lead to not just the major leagues, but the Baseball Hall of Fame in Cooperstown.

Overcoming the Odds

But reaching the pinnacle of success means overcoming adversity along the way. “The Captain” recounts how Jeter, the high school player of the year as a senior in Kalamazoo, got passed over by several major league clubs in the 1992 draft. The first five clubs selected players from the collegiate ranks, a move that so infuriated longtime Houston Astros scout Hal Newhouser that it prompted his resignation, as he believed the Astros should have selected Jeter with the draft’s first pick.

But falling in the draft meant the Yankees could fulfill Jeter’s childhood dream by selecting him with the sixth pick, and he repaid their faith in him — eventually. In the short term, Jeter had to reckon with a year of rookie ball in 1992 that saw him make 56 errors in a single season. In between games, he spent $400 per month on long-distance calls home, where he vented to his parents about the loneliness of life in the hot Gulf Coast League.

In time, however, the player who began as a thin, even scrawny, shortstop built up his skillset and his confidence. Prior to the draft, Yankees scouts believed that growing up in a biracial household in 1970s Kalamazoo gave Jeter skills that he would later need to drown out critics. By the time the 1995 season rolled around, Jeter had made his big-league debut for the Yankees; while not yet an everyday player, he impressed scouts with his potential.

Building Blocks for a Dynasty

The Yankee team that joined in 1995 had as much potential as Jeter himself. During his time in the minors, Jeter had played with people like Jorge Posada and Andy Pettitte, players who would make up some of the core of the Yankees for years to come.

When Major League Baseball suspended Yankee owner George Steinbrenner from day-to-day operations of the team, general manager Gene Michael stockpiled prospects like Jeter, Posada, and Pettitte, creating the nucleus of what would become a baseball juggernaut. More adversity lay ahead, however, in the form of a heartbreaking loss to the Seattle Mariners in the Yankees’ first playoff appearance in 14 years.

The first episode of “The Captain” concludes with a raw, but as yet unproven, Jeter accompanying the Yankees to (but not playing in) the stunning defeat in the 1995 playoffs. They did not know it at the time, but both Jeter and the Yankees lay on the cusp of baseball greatness.

The next episode of “The Captain” aired on ESPN on Thursday, July 21. Episodes are also available for streaming via ESPN+.

Mr. Jacobs is Founder and CEO of Juniper Research Group and the author of the book The Case Against Single Payer. He is on Twitter: @chrisjacobsHC.