Derek Jeter was the face of the Yankees for the better part of 20 seasons. That's no easy feat, especially in New York, where the fans demand success every night and the media is there to chronicle every swing, every hit and every miss.
Jeter won five World Series with the Yankees and finished with 3,465 career hits, sixth-best in MLB history. On Jan. 21, 2020, Jeter — named on 396 of 397 ballots — was voted into the Baseball Hall of Fame.
For every win and loss, Jeter was there to answer questions from reporters. His answers may have been bland — something "El Capitan" has admitted to in the past — but he stood there and delivered, night in and night out.
We gathered together Newsday sportswriters who chronicled Jeter at various points in his career, for either a long time or a very short time, and asked them to share what it was like to cover the Hall of Fame shortstop.
Neighborhood run-ins
For a while, Derek Jeter was my neighbor.
Not in a next-door, can-I-borrow-your-blender proximity, but we lived within a few blocks of each other on the Upper East Side of Manhattan. Me in the early years of my job as Newsday’s Yankees beat writer, him just starting out as the future Hall of Fame shortstop.
I’d bump into him at the local Starbucks. Maybe because it still was early in his career, or maybe because New Yorkers try to be extra-indifferent about celebrity encounters, the other coffee-drinkers mostly ignored him. Since I spent more time around Jeter those days than with any of my closest friends or family members, those conversations didn’t really go beyond “See you later in the Bronx.”
As we all know, Jeter stayed pretty buttoned-up with the media once he got inside a ballpark. He was always cooperative. Just relied on his standard shtick, never making waves. If Jeter truly was excited about something or ferociously angry, both sentiments were delivered in a similar monotone, usually punctuated by a chuckle.
But there were a couple of times in the neighborhood when Jeter stretched the boundaries of his personal code.
One involved me standing with an out-of-town friend on a street corner, waiting to cross, when a large black SUV, sort of Escalade-sized, raced up to where we were positioned, honking the horn maniacally.
At roughly the moment the two of us were bracing for impact, the SUV came to a sudden stop. As soon as I caught my breath and readied my arm for the standard pedestrian one-finger salute, that’s when the tinted window on the driver’s side slid down to reveal a grinning Jeter, visibly pleased with his antics. We said hi, and then something along the lines of “See you later in the Bronx.”
Spotting Jeter outside of his ride on the UES happened about as often as him not busting full-speed out of the batter’s box. As his Yankees grew into a dynasty, the team’s Most Valuable Bachelor became a magnet for non-baseball attention, and Jeter made it clear that his social life was off limits for discussion.
But one night, after having a late dinner with my parents, I decided to walk back to my apartment and wound up bumping into Jeter on the sidewalk. By that time, his reported dating roster was a Hall of Fame in itself, but I didn’t recognize the woman he was with.
We exchanged hellos, as usual. On this occasion, though, Jeter introduced me to his friend, whose name was Vanessa. I was stunned that he revealed even that much, as carefully as he guarded his off-field space.
We chatted until the light changed, then headed in different directions. It wasn’t until days later that I discovered — along with the rest of the world — that Vanessa was actually Vanessa Minnillo, the MTV VJ (remember those?) and the two supposedly were dating.
These fleeting snapshots were about as close as anyone in the New York media got to Jeter — away from the clubhouse — during his playing career, and as brief as they were, it was a nice changeup to interact when he didn’t have the full pinstriped armor on.
I covered Jeter on a daily basis as a Yankees beat writer for only the first three seasons of his 20-year career, but whenever I dropped by the clubhouse, either later as the Mets beat writer or in my current gig as columnist, he would make some reference about recalling days “when we were both much younger.”
We stopped being neighbors a while ago. I’m still on the UES, but Jeter has set up shop full-time in Florida now with his family. He continues to follow his script. The tiny little outtakes, however, are what I tend to remember.
'I wish they would shift me'
In 20 years in New York, Derek Jeter excelled in speaking often and saying next to nothing.
It was how Jeter, as well as the Yankees, liked it.
I started covering the Yankees in 2009, so I didn’t cover Jeter nearly as long as others in town did, but it didn’t take long to admire his day-in-day-out consistency — both in terms of performance, keeping a big-picture perspective on the inevitable ups-and-downs of a given season and, of course, his role as team spokesman in which he never misspoke.
Still, occasionally, very occasionally, Jeter’s true feelings on something emerged. One such occasion occurred in 2014.
I approached Jeter at his locker in Baltimore before a game at Camden Yards. Though he didn’t speak in sound bites, the shortstop was readily available and easy to approach regarding just about any baseball-related topic. I needed to ask him, on behalf of colleague Jim Baumbach, a few questions. Jim, an award-winning takeout writer who previously covered the Yankees, was working on a long-form piece about teams’ increasing reliance on data, the story’s primary focus in examining the exploding trend on the use of the shift.
“Yeah?” Jeter said with a wry smile when I told him the topic, “what do you want to know?”
In answering the questions, it became clear that Jeter, while not outright hostile toward the sport’s movement toward analytics, was not a fan, either.
“Let’s just say,” he said, giving the same wry smile, “I’m getting out [retiring] at just the right time.”
(It should be noted that Jeter’s Marlins, like all teams, have bulked up their analytics departments in recent years).
What was most interesting, however, was his specific thoughts regarding the shift. While trying not to criticize players whose averages across the sport were being ruined by it, Jeter, who almost never offered praise for himself, provided a brief window into the self-confidence that is a part of just about every top-flight athlete.
"They don't shift me. I wish they would shift me,'' he said.
Jeter, of course, accrued 3,465 hits in his career, ranking him sixth in MLB history. The prospect of overshifted fielders made his mouth water.
"I don't care where they shifted, which direction they shifted, but I wish they would,” he continued. “You know how easy it would be to get hits if somebody played a shift? The whole infield on one side?”
Jeter briefly caught himself.
“I'm just talking about for me . . . I should be able to make an adjustment to that. I can only speak for myself.”
After a few more questions, I thanked him and started to walk away.
But there was one last smile and comment before I took a step.
"Write that: I wish they'd play a shift on me.''
'Party On'
The Hall of Fame announced on Tuesday night that Derek Jeter had been elected, with his name appearing on 396 of 397 ballots. Over the next 18 hours, about a dozen colleagues, friends and people I’ve covered reached out to ask if I was the one voter to omit Jeter.
There’s a reason for this. For better or worse, I was among Jeter’s least favorite media members.
Perhaps you remember Visa had an ad campaign in the early 2000s that featured Jeter and George Steinbrenner. It was all about going out on the town with your card, and one even included them in a conga line. That campaign sprung directly from a story I wrote in February 2003 for the Daily News.
Five or six weeks earlier, one of my colleagues had a one-on-one with Steinbrenner and asked about the possibility that Jeter would be named team captain. The Boss questioned the way Jeter was conducting himself, saying, “When I read in the paper that he’s out until 3 a.m. in New York City going to a birthday party, I won’t lie. That doesn’t sit well with me.”
Editors being editors, I was sent to Tampa before spring training opened to try to get a response from Jeter. He had a residence in Tampa and was working out at the Yankees’ minor-league complex. Because spring training hadn’t begun, media was not admitted, so we stood on the sidewalk next to the driveway.
Jeter knew me — or at least my face — and stopped as he was exiting the complex. There, he answered a few questions I asked about the Steinbrenner interview. It wasn’t the conversation he wanted to have, but he gave professional answers. He said, essentially, that every working person has a boss and that those bosses’ opinions need to be heard.
Asked if he needed to change anything to re-shape the way Steinbrenner viewed him, his answer was “no.” Essentially, he was saying, "How’s it working for me so far?"
I wrote the story with his remarks. On the Daily News' back cover the next day was a photo of Jeter with the headline “Party On!” The editors at the News were so delighted with it, they made T-shirts with the back page on it and sold them.
Jeter wasn’t happy about this. When spring training opened, he inquired to the media assigned in Tampa where I was. Day after day, he continued to inquire.
I was the college basketball reporter, but between the Big East’s conference tournament and the start of the NCAA Tournament, I was sent to Tampa to work on the Yankees for four days.
When I walked in for the first workout that Monday, my colleagues covering the team were gleeful — here comes the guy Jeter has been looking for! They told me he’d sought me out. They explained that he’d been asking for me because he wasn’t happy.
When he rolled in, I approached him and told him I understood he wanted to speak to me. “Now I am here,” I said.
He told me he thought the story had been “unfair.” I asked him what in the article was inauthentic. He was bothered by the “Party On!" back page. I tried to explain to him that reporters don't write the headlines. He wasn’t thrilled.
I found out how much this bothered him in 2013, when he was rehabbing in Tampa after his ankle injury. I was sent there by the Daily News to get stories about Alex Rodriguez, who was rehabbing from hip surgery.
I was on the sidewalk — as I recall in a rainstorm — and Jeter waved me and another reporter in. We discussed his rehab, and maybe A-Rod, before the questions petered out into an awkward silence. That happens a lot. I try to add levity to those circumstances, often by saying something akin to “if you have something inflammatory to say, now is the time.”
“If I did, I wouldn’t tell it to you!” Jeter responded. He went on to recount everything that transpired from a decade earlier, blow-by blow. I’d never realized it bothered him that much.
That said, he’d always been a professional with me in our interactions and never let on that he was upset. He was always admirable as an interview subject.
And, by the way, yes — I voted for him for the Hall of Fame.
Taking his cuts at the Boss
The year was 1999, and the Yankees were getting ready for a game against the Red Sox at Fenway Park.
The visitors' clubhouse at Fenway is small. Tiny. A phone booth put in a closet stuffed into a crawl space.
When the Yankees are in Boston to play the Red Sox, it seems even smaller because of the number of media from both cities that crowd into the space that barely fits the 25 players, coaches and staff.
It was into this packed room that I saw George Steinbrenner — in all of his Boss glory — stride in the main entrance.
Just to the right of the entrance are a couple of lockers. The closest to the door, if I remember correctly, belonged to Derek Jeter.
The 25-year-old Yankees shortstop — a two-time World Series champion in his first three full big-league seasons — was idly fiddling with a bat.
As Steinbrenner walked by, Jeter quickly turned and swung the bat directly toward The Boss’ midsection, stopping just before it touched Steinbrenner’s belly. The Boss laughed. Jeter pulled the bat back and smiled, embraced Steinbrenner and acted as if the entire bat thing hadn’t just happened.
I don’t think there’s another player I've ever covered who, in the space of an eyeblink, in a room that size, with media stationed in every corner, would have A) thought to playfully swing a bat in the Boss’ midsection and B) actually done it and C) acted as if it were an entirely normal thing to do afterwards.
The Boss loved it. But don’t try this with your boss today. Jeter could get away with it. You and I couldn’t.
Jeter never forgot a called strike three in high school
I went to Kalamazoo, Michigan, in 2012 on an assignment to commemorate the 20th anniversary of the Yankees drafting Derek Jeter.
I looked at his high school yearbooks in the public library. I stood in his fourth-grade classroom as his teacher showed me where Jeter told everyone that he would one day be the Yankees' shortstop. And I visited his childhood home, where a pair of sisters were busy moving in boxes from their car. They had bought the house just a few weeks earlier and — get this — had no idea about its Jeter connection until their home inspector said, “So which room do you think was Derek's?”
But the best story I came across was from his high school baseball coach, Don Zomer. While sitting in the grandstand at the high school baseball field that now is named after Jeter, Zomer told me that Jeter struck out only once during his senior year, on a called strike three.
While diplomatically pointing out that the call was made by a respected umpire who still worked high school games, Zomer laughed and said the umpire "still to this day swears he was right." But that night I got the umpire, Dick Bird, on the phone, and he wasn’t as certain.
"I might have missed the pitch,” he said somewhat sheepishly.
Then he asked me for a favor. If I ever happened to speak with Jeter about that strikeout, he said, could I pass along that message? It was almost as if it had been on his conscience all that time. “I figured,” Bird said, “he might get a laugh out of that.”
Then he asked me for a favor. He said that if I ever happened to speak with Jeter about that strikeout, if he could pass along that message. It was almost as if it's been on his conscience all this time. “I figured," Bird said, "he might get a laugh out of that.”
I then called Newsday teammate David Lennon, who was in Toronto with the Yankees, and asked him to relay the umpire’s words to Jeter.
Jeter told Lennon he remembered that strikeout. "He knows he missed it," Jeter said. "I swing at everything. If it was close, I'm swinging at it.
"I've always been that way."
Page A16 in Newsday, Sept. 30, 2012.
'Aren’t you going to ask me who my friend is?'
In 2007, I was sent to Yankees spring training to work on a feature story, which was a little unnerving because I had spent most of my career covering the NBA.
In 2006, the Yankees' season had ended “early” when they lost to the Detroit Tigers, 3-1, in the first round of the playoffs. I went on a fishing expedition and asked Derek Jeter what he had done with his longer-than-expected offseason. To my surprise and delight, he launched into a story about how he had toured Europe with a “friend” and what a great time they had.
Jeter went on and on about how great it was that no one recognized him in Europe. He then casually mentioned that it helped that his “friend” was more famous in Europe than he is. As soon as I heard that, my reporter instincts kicked into overdrive. I assumed that Jeter was over there with a celebrity girlfriend. I also knew that he was notoriously private and likely would shut down the interview as soon as I asked whom he was with.
So I figured that had to be my last question. In the meantime, I tried to get as many details as possible, asking him about what cities he had visited, what sights he had seen, etc. I was calculating how many questions I could ask before I went for the big one when Jeter started laughing.
“Aren’t you going to ask me who my friend is?” he said.
Turns out the friend was Michael Jordan, who had brought Jeter on a European publicity tour so he didn’t have to hang out at home and watch the playoffs he wished he had been in.
I always tell this story when I speak to journalism classes. It shows how you can get so worried about what you are doing that you can almost miss the obvious.
That one time when I saw Mr. Cool lose his cool
Seeing somebody go against type is always memorable.
Particularly when it’s Derek Jeter being anything less than the calculatedly cool character he usually was in public settings. As in going after a reporter (not me) in the Yankees’ clubhouse.
More on that in a few paragraphs.
I covered my fair share of Yankees games for an area newspaper from 1996 to 2001, never as a beat reporter but enough to feel comfortable in that dynasty’s clubhouse. It was the first six seasons of the soon-to-be Hall of Fame shortstop’s career.
And, from the start, Jeter was always in control. He learned quickly how to say just enough in media scrums to give reporters quotes but without divulging much, if any, real information. He was polite, if detached, a trait that would only grow through his career.
As a backup writer, I developed zero relationship with him.
But it wasn’t hard to sense he was going to be a special Yankee.
Joe Torre himself implied that numerous times in Jeter’s rookie season, if not saying it outright.
The baseball lifer, in his first season managing the Yankees and not quite the revered figure he became during 12 seasons in their dugout, would spend Jeter’s rookie year raving about his professionalism, maturity and work habits.
Torre almost sounded reverent at times while talking about the youngster, implying he was an “old school” type of player who would have fit in well in Torre’s playing days.
And the respect was mutual. Jeter always referred to his manager as “Mr. Torre.” That seemed to please Torre as well.
That’s the setup. Now back to the atypical Jeter moment.
Don’t ask me what season it was. Don’t ask me the month. Don’t ask me the Yankees’ opponent that day. Or night.
But during the pregame clubhouse access as I was interviewing another Yankee (don’t ask me which player), all of a sudden there was a commotion on the other side of the room.
Jeter was raising his voice as a reporter walked away from his locker, trying not to engage him further.
Again, I’m not sure whether Jeter was doing a group interview or if this reporter had done a one-on-one with him. But something the reporter asked or said or did totally set off Jeter.
I remember it getting very quiet in the clubhouse as the reporter — given a wide berth by the other players and media members — tried to move away. It didn’t seem as if the reporter was doing that as a sign of disrespect, just as a genuine desire to escape what was turning into an ugly situation.
And maybe it would have ended at that.
Unfortunately, the reporter walked away wearing a nervous, odd smile.
Somehow Jeter saw that. And now he was repeatedly telling the reporter to wipe the smile off his face.
Nothing more came of it and the confrontation was never in danger of becoming a physical one.
But I had never seen Jeter act like that before. Or since.
For that one moment, Jeter went against type.
And it was memorable.
Jeter, A-Rod and the Macaroni Grill
The sports reporting world was quite different in 2005.
I was on the Yankees beat then, and on my to-do list in spring training was to take the beat reporter for their Triple-A affiliate out to eat to get to know him better.
This way, if I wanted to see if a Yankees prospect was a late scratch from the lineup around trade deadline time, I had a contact on the scene to call.
Yes, amazingly, minor-league scores, lineups, gamecasts, etc., were not yet available on the Internet.
So that spring I went about my relationship-building exercise and invited the Triple-A Columbus reporter out for some fine dining … at the Macaroni Grill.
Don’t laugh too hard, because guess whom we saw sitting at the corner table?
Those famous pinstriped frenemies, Derek Jeter and Alex Rodriguez.
Remember, this was one year after the Yankees acquired A-Rod in the blockbuster of all blockbuster trades, and the relationship between the two of them was a hot topic.
They insisted several times they still were good friends, though their body language often said otherwise. So seeing them at a restaurant on a random afternoon during spring training was somewhat surprising.
Later that day, before the Yankees hosted an evening exhibition game, I approached Jeter at his locker when nobody else was around and we discussed his lunch date.
Or at least I tried to.
I mentioned that I had seen him at the Italian chain dining with A-Rod, and, by the way, isn’t that proof that all the talk about their soured friendship was much ado about nothing?
Jeter, not surprisingly, wanted no part of the conversation.
“Don’t make news out of it,” he said before walking away.
Worst part is, I didn’t even get a chance to ask what he ordered.
Those final days
Having spent much of my time covering baseball crosstown with the Mets while at The Bergen Record, I’d grown accustomed to the stars of the franchise serving as the very public face.
David Wright was at his locker before and after every game, available to comment on any issue with the team and willing to engage on the Giants or Knicks or any other sports topic. Jose Reyes would be the first person in the room and never hide. Billy Wagner would, well, bluntly answer any question.
Derek Jeter was different. His locker was placed strategically near the back door of the clubhouse at Yankee Stadium, and he might flash in for a moment before a game, disappearing back through the door to the hidden rooms before the pack of reporters could close in.
After a game, often you’d wait, watching the time before deadline tick away, before he might show up. And then he would be cautious with his words, even boring.
It was a survival skill for a star in the chaos that often engulfed the Yankees. What it wasn’t was an act.
In his final days as a player in 2014, the knives had come out. Jeter had hit .207 in April of that final season and went through an 0-for-28 slump heading down to the final week of his career. But with fans at Yankee Stadium cheering him on, he had a final homestand in the Bronx in which he hit .353 over eight games, shaking off age and injury, rising to the moment.
It was a special time. The Yankees opened the gates to the stadium an hour early so fans could cheer the simplest moments -- jogging in the outfield to loosen up, his turn in the batting- practice cage.
“This is the time for me to call it a career after this season,” Jeter said in the midst of that final homestand. “Some times things are difficult. Some times they come a little bit easier — not easy, but they come a little bit easier at times. You’ve got to continue to battle. This is a game of adjustments. I’ll continue to make those adjustments until I’m out of games. I’m well aware of the fact you can only do this for so long. Careers only last so long, especially athletic careers. I’m well aware of that. I’ve come to grips that this is the last season.”
There were no tears from Jeter as the days wore on. Then, on his last day at the Stadium, he came up with the sort of moment that etches a place in history.
He played shortstop one last time. Then, with the crowd still waiting for the highlight, he singled in the game-winning run in the bottom of the ninth inning. And finally, he raised his arms in celebration.
In the locker room afterward, finally he lowered his guard, opening up about his emotions, talking about his last reflective moments on the field. Finally, he said, “I don’t know what to tell you. Write what you want and put my name at the bottom of it.”
The last hurrah
Beyond the big hits and big plays and big championship rings, part of the genius of the Derek Jeter mystique was his opaqueness, a blank slate of sports herodom onto which fans could project . . . well, whatever they wanted.
That went for journalists, too, given how little of a window he offered us into what he really was thinking.
Regular baseball writers got to know him to a point, much like as an NFL regular I got to know Eli Manning, which was only a little — just the way he wanted it.
Those of us in the writing game who were only occasionally in Jeter’s orbit were left to experience him with the same detachment as fans, allowing for an unadulterated view of Jeter the player. And he was pretty great.
When I think of Jeter, I first think of July 9, 2011, when I had a chance to go to that day’s game at Yankee Stadium and did not. He hit a home run for his 3,000th career hit — in a game in which he went 5-for-5 and drove in what proved to be the winning run.
There went a once-in-a-lifetime chance to see history as Jeter’s career began to wind down.
Turned out he was not done. On Sept. 25, 2014, I was assigned to help cover his final home game. You know what happened.
The Yankees blew a 5-2 lead in the ninth inning, allowing Jeter to drive home pinch runner Antoan Richardson from second base with the winning run with a textbook Jeter-ian single to rightfield.
I have been fortunate to witness many hundreds of professional sports events over the past half-century, and that moment for me ranks second only to the 10th inning of Game 6 of the 1986 World Series.
My unoriginal tweet seconds later: “No words.”
But of course, there were words, and while Jeter spoke in a packed interview room, I was sent to the locker room, where the supporting actors in the drama were marveling, just like the rest of us.
Relief pitcher David Robertson, who blew the save, said, “I told him, 'Thanks for saving my butt out there; I really appreciate that.’ He said, 'No problem' and went right on to the next person."
For Richardson, who scored a total of four runs in 20 career major-league at-bats, it meant a lifetime as a trivia answer.
“Just a thrilling moment,” he said in a locker room so uncrowded that we veered off into a discussion about the recent College World Series victory for his alma mater, Vanderbilt.
After the game-winner, CC Sabathia goaded Brett Gardner into dumping the contents of a Gatorade bucket onto Jeter’s head.
“If this was a movie, I would probably get up and walk out and be like, ‘No chance,’ ” Sabathia said. “But it’s him. It’s Jeet.”
That is what I remember about the night Derek Jeter bade farewell to Yankees fans: Enjoying the spectacle as an observer, then having other observers tell me what it was like from field level.
As for Jeter, his performance spoke for itself.
