Red Sox

ESPN’s ‘The Captain’ is more akin to Yankeeography than ‘The Last Dance’

Notoriously tight-lipped Derek Jeter still won't spill the beans in 7-part ESPN documentary

By Chad Finn

July 23, 2022

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On the Fourth of July, 1939, a dying Lou Gehrig bid farewell to the Yankee Stadium crowd with the impossibly graceful declaration that he considered himself to be the “luckiest man on the face of the earth.”

In a way devoid of all irony and tragedy, I’ve always thought that phrase was a fitting description of another legendary Yankee of a later generation.

Once upon a time, and perhaps still, Derek Jeter knew it himself.

“I don’t think there’s a person in the world that has been more spoiled than I’ve been,’’ he said at the parade after the 1998 Yankees juggernaut won the World Series, their second in his three full seasons to that point.

Substitute “lucky” for “spoiled” if you wish, but the sentiment was true. Jeter was the face of the Yankees dynasty — and it was terrifying to see him in the batter’s box with the game on the line, a cue-ball game-winning single to right field all but certain — but he was surrounded by an extraordinary amount of talent in his heyday. He epitomized the Yankees, but he never had to carry them.

(I used to like to needle Yankees-fan friends — while making the unassailable case that Nomar Garciaparra was better — that Jeter was the greatest role player in sports history. Call it evidence that there was such a thing as trolling before the internet took over the world.)

The aforementioned scene, shown in the second episode of ESPN’s ongoing seven-part documentary series on Jeter, titled “The Captain,” was a rare moment of candor during his playing days, when his mode of operation was to be unfailingly polite and reveal absolutely nothing of substance about himself.

Jeter’s methods were effective, particularly considering the tabloids’ chronic interest in his active social life with a lineup of Hollywood girlfriends. There was never a hint of scandal, though he acknowledges with his usual resting smirk-face in the documentary that he was fortunate to play before technology changed the parameters of fame.

“I’ve joked before,” he said, “if there were phones back then, my career would have been three years long.”

Anyone expecting Jeter to ditch his pinstriped veil during this documentary is going to be left . . . well, not exactly wanting more, because seven parts is at least two parts too many. This could have been trimmed to five episodes if director Randy Wilkins — an unabashed Yankees fan, as is ESPN chairman Jimmy Pitaro — cut every Jeter self-reference to being “all about winning” or some variation.

Banality by design proved a savvy tactic for Jeter in navigating the New York media, but that approach is counterproductive to a documentary series. He’s at his most compelling when he talks about growing up with a Black father and white mother in Kalamazoo, Mich., and his lifelong guardedness is beyond understandable when he recalls specific instances of encountering racism. But otherwise, he acknowledges potentially controversial subjects, such as the fracturing of his friendship with Alex Rodriguez, but leaves the expounding upon them to others.

Episode 3, which airs Thursday at 9 p.m., gets into the relationship with Rodriguez, who made the critical mistake of telling Esquire magazine the truth in 2001.

“Jeter’s been blessed with great talent around him,” said Rodriguez. “So he’s never had to lead. He doesn’t have to, he can just go and play and have fun, and hit second.”

The comments clearly still irk Jeter.

“You can compare statistics all you want,” he says. “I don’t care who hit more home runs, who had more RBIs, who had more stolen bases. I compare who won more. We won. That was it.”

He was all about winning, you see. Just as long as he still got to stay at shortstop into his 40s.

The most interesting thing about Jeter might be the depth and staying power of his grudges.

“I have a list of people in my head who doubted,” he says. “I remember exactly what you said and when you said it and what you were wearing when you said it.”

The grudge-holding is something Jeter has in common with Michael Jordan, and pretty much the only through line from “The Last Dance” — the sprawling, hugely entertaining look at the 1997-98 Chicago Bulls — to “The Captain.” Like Tom Brady in “Man In The Arena,” another ESPN docuseries, true candor is more of a guise than a feature.

After watching the first three episodes — ESPN provided a screener for Part 3 — I’m left with few if any new insights into Jeter, and one yet unanswered new question: Why did he decide to do this? Is it an attempt to keep up with Jordan and Brady as a so-called brand? Is he bored, eight years after retiring and a few months after leaving the Marlins’ ownership group? It certainly wasn’t to reveal any more about himself than we already knew.

“There are things I still won’t talk about,” he acknowledges at one point.

I suppose “The Captain” is decent viewing during a slow time in the sports calendar, but it has more in common with a standard Yankeeography on the YES Network than “The Last Dance.” I can’t imagine anyone who is not a dyed-in-the-polyester Yankees fan was interested in listening to a talking head rhapsodize about the secondary lead Jeter got at second base in the third inning of Game 3 of the 1996 World Series. But it’s here.

The base-running minutiae is one more reminder that, yes, Jeter was a winner, at least until he captained the Yankees team that blew a 3-0 lead against the Red Sox in the 2004 ALCS. But it’s also a reminder that like Jeter the shortstop, “The Captain’’ has severely limited range.