The Time I Tried and Failed to Profile Derek Jeter

An expert at deflecting. Photo: Lynne Sladky/AP/Shutterstock

On Monday night, episode one of The Captain, a seven-part miniseries chronicling the career of Derek Jeter, premiered on ESPN. I haven’t seen it yet, but the show, clearly patterned after the pandemic hit The Last Dance, is directed by Spike Lee protégé Randy Wilkins and seems to have all the gloss and crisp production of a typical, high-quality ESPN documentary. For entertainment purposes, it’ll do the trick.

Though The Captain promises to be a comprehensive portrait, I can’t help but wonder how much of the “real” Jeter we’ll get to see because he has been so damn good at hiding it for the past quarter-century. This opacity is part of what made him impressive: Jeter was able to hide in plain sight for decades even though he was the star shortstop for the New York Yankees. There was once a “Page Six” article about how he gave “commemorative autographed-memorabilia gift baskets” to his one-night stands, and the story somehow didn’t hurt his reputation one whit.

This is to say, Jeter was untouchable. As I learned.

When I joined New York Magazine in 2008 as the primary sportswriter for a non-sports publication, one of the first assignments from my non-sports-fluent editors was to “write a profile about Derek Jeter as he approaches retirement.” I think they thought the publication’s prestige, and the lure of a cover story, would inspire Jeter to grant a long, reflective sit-down. We’d hire an avant-garde photographer to shoot him, he’d pour his heart out, and we’d all win a bunch of awards. I was very familiar with Jeter’s press reticence, though, and I knew that getting them the story they wanted would be impossible. (When I requested “an hour-long in-depth interview with Jeter” to the Yankees’ publicity department, they were polite enough not to laugh in my face. But I know they wanted to.) My editors then suggested half an hour and a photo shoot. That wasn’t happening either. The only way I’d get any chance to talk to Jeter would be during the normal pregame locker-rooms scrums with all the other reporters, in which Jeter spouted the sort of drive-by empty athlete-speak at which he excelled.

But I did want to give my new editors something. So I came up with an idea: I would request press access to 30 consecutive Yankees home games. Before each one, I would head to the Yankees’ locker room and ask Jeter a single question. After 30 days of daily one-minute interviews, I’d have enough Jeter insights to cobble together some sort of profile. It wasn’t a traditional approach, but maybe that would work in my favor. At the very least, it would be something different.

The first four days produced interviews about as banal as you’d expect. “We gotta play a good game tonight,” “It’s special being a Yankee,” “You take it one day at a time” — that sort of stuff. But by the fifth game, with the same kid popping by his locker to ask him one minute’s worth of questions at the same time every day, Jeter sensed something was up.

“Hey, didn’t we just do this yesterday?” he asked me as I approached with my steno pad.

“Yes, but I have a different question this time,” I said.

“Well, I would hope so,” he said.

I don’t remember what I asked, but the answer I received was, inevitably, a polite, canned one. But I returned the next day nevertheless, to Jeter’s bemusement. I explained that I was trying to write a profile of him by interviewing him for one minute every day.

“That’s weird,” he said.

“I know,” I said.

“All right, go ahead then. What’s today’s question?” he said, smiling. “You have one minute.”

It kept on like this, with me giving it a good-faith effort and Jeter cheerfully but bloodlessly providing me with nothing in return. By the 20th day or so, it was obvious it wasn’t really going to work. But I had begun to enjoy running up the hill every day, and I sensed it sort of tickled Jeter, too. As the days ticked by, he began chuckling the second I started walking up to him. One time, he called me 60-Second Will. Another time, he joked, “You gonna ask me about my mother? I’ll try to sum her up in one minute for you.” He was clearly amused by my dedication to this obviously failing gambit. My favorite moment was the day when, before heading out for batting practice, he pretended to take my notebook and my pen before turning to me and saying, “Okay, tell me about your growing-up experience.”

On the last day of this experiment, I went up to Jeter’s locker, as usual, and told him this was it — I wouldn’t be bothering him anymore. He grinned.

“Did you get anything?” he said.

“No, actually,” I admitted. “I have no idea what I’m going to write about.”
He clucked his tongue and gave a slight nod, as if to say, Well, then my work here is done. I thanked him for his time and told him I hope he likes the piece, whenever I figured out what it would be. “Yeah, good luck with that,” he said. “Sounds like you’ll need it.”

The story I ended up writing is the very definition of a write-around: It’s a profile of Jeter without a single Jeter quote that didn’t come from a press conference. (Meanwhile, Jeter hit .334 that season with 18 homers and finished third in MVP voting, at the age of 35. You could argue it was his last great season.) I didn’t even mention my dumb interview-a-day project, cementing its ultimate failure. But I still think the piece holds up. It does a good job of describing that you-see-me-but-you-don’t-see-me nature of Jeter’s, the way he stood in front of every camera for 20 years and never gave away anything. That in itself is an incredible achievement of discipline and caution. Heck, it’s the sort of repeatable skill that makes a great baseball player.

I brought a copy of the magazine with my feature in it to the clubhouse during that year’s postseason, which would end with a Yankees World Series championship, still the team’s most recent to date. Jeter wasn’t at his locker, so I just left it there for him with a Post-it note: “Thanks for your help.” (I resisted the urge to put the word help in quotes.) The next day, I came back and saw his teammate Mark Teixeira doing the magazine’s crossword puzzle. Jeter wasn’t at his locker that day, either. In fact, I haven’t interviewed him since. I feel like I know him just as well today as I did then. That probably should make me feel like a bad reporter, but I can take solace in the fact that I’m not sure anyone else has gotten to know him any better since then either — which, as always, was by his own design.

The Time I Tried and Failed to Profile Derek Jeter