The Captain: The Journey of Derek Jeter

by Ian O'Connor

  “Most guys make changes in how they wear a uniform over the years,” said Yankee equipment manager Rob Cucuzza. “Derek Jeter has worn his uniform exactly as he’s worn it from day one.”

  Millions of Little Leaguers were trying to wear his number 2 with the same grace. Jeter was not beloved merely because he was a four-time champion who delivered big October hits, patented that running flip play at the plate, and made those acrobatic midair throws from the hole.

  He was beloved for signing autographs for as many kids as he could accommodate, for playfully asking fans from the on-deck circle if he should swing at the first pitch, for never disrespecting an authority figure, and for making sure he had fun on the playing field.

  In 2001, Jeter’s former teammate, David Cone, returned to the Bronx as a member of the Red Sox and tried to ignore Jeter while the shortstop approached the plate in the first inning. But Jeter tilted his head sideways and shot a crooked stare at the mound, announcing to Cone that he would not step into the box until the pitcher lost his game face and acknowledged him.

  “So I finally looked at him,” Cone said, “and Jeter gave me this goofy face. It was utterly disarming. And I was like, ‘Come on, don’t do that.’”

  Jeter ripped Cone’s first pitch for a double to right and went 5 for 5 for the night.

  Parents read and heard about the way Jeter carried himself, saw it with their own eyes, and they passed down their admiration to their children. Truth was, Jeter “got it” at a time in professional sports when those who “got it” were in dangerously short supply.

  He understood the power of Yankee tradition and mythology, so it was no surprise that Jeter was a steady guardian of the empty locker next to his, the one that belonged to Thurman Munson, the catcher and captain killed in a 1979 plane crash. Sometimes visitors to Jeter’s stall in the far left-hand corner of the cramped Yankee clubhouse would forget the space next door was a shrine, and they would stand right there, or drop a piece of equipment or a bag right there, before the shortstop asked them to show a little courtesy and respect.

  On Old-Timers’ Day, even with some of the living pinstriped legends eager to spend time around him, Jeter was careful to avoid overstepping his bounds. He summoned the nerve to talk to Joe DiMaggio only one time, in the dugout, and the shortstop was shaking in his spikes.

  “I heard a lot about you,” DiMaggio told him.

  “Nice to meet you, sir,” Jeter replied.

  And that was it. Jeter quickly moved past the Yankee who projected a forbidding aura, the Yankee who wore a Do Not Disturb sign around his neck, and got himself ready to play the game.

  “I admired him from afar,” Jeter said. “I didn’t get an opportunity to know him, but I wish I would have.”

  DiMaggio and Jeter were linked first and foremost as the greatest Yankees of their generations, but also as men fiercely protective of their privacy despite relationships with high-profile starlets the likes of Marilyn Monroe and Mariah Carey.

  It was easier in DiMaggio’s day to maintain an air of mystery; Jeter had to navigate an exploding media environment defined by never-ending coverage of celebrities, outlets multiplying by the hour, and technological advancements just starting to put camera phones in the hands of trigger-happy bar patrons.

  But somehow, some way, Jeter negotiated the electronic jungles of Manhattan and Tampa without getting photographed in compromising positions, alcoholic beverage in hand. By 2002, he had already dated more beautiful women than Hugh Hefner could count, his list of significant others including Miss Universe Lara Dutta, actress Jordana Brewster, and singer Joy Enriquez, who was reportedly introduced to Jeter by none other than a smitten Alex Rodriguez at the 2001 All-Star Game.

  Jeter was said to have stolen Enriquez’s affections away from A-Rod, who, of course, had it coming to him. The Jeter-Enriquez relationship “has my total blessing,” Rodriguez would say, though A-Rod’s blessing was not one Jeter was actively pursuing.

  Regardless, as New York’s most eligible bachelor, Jeter was a player without scars. “He almost never gets photographed out,” said Jim Leyritz, his friend and former teammate, “and think about all the high-profile girls he’s dated. None of them come back and say he’s a lousy lover, he’s not good in bed, he’s cheap, he doesn’t pay for this. You don’t hear any of that. He’s either real smart, or there’s nothing bad about him.”

  Jeter was smart enough to keep his circle of confidants tight, a circle that defied the celebrity entourage prototype. He remained close with a grade-school friend and aspiring golf pro from Kalamazoo, Doug Biro, and with a former minor league teammate, Sean Twitty, both salt-of-the-earth types. Jeter spent time out with Rafael Oquendo, his personal trainer. Another former minor league teammate, R. D. Long, was the resident good-natured hellion of the group, serving in the role of Derek’s alter ego.

  Out on the town, Jeter understood he had an image to protect. He never snapped at fans or waiters who approached for autographs in the middle of dinner, even if the request was made as his forkful of chicken parm was halfway in his mouth.

  By all accounts, Jeter never turned away kids; sometimes he would ask an overbearing adult to return when he was finished eating. His behavior stood in stark contrast to that of DiMaggio and Mickey Mantle, who could act boorishly when dealing with fans of all ages.

  Billy Martin, of all people, repeatedly rebuked DiMaggio for “treating people like shit,” according to Ray Negron, the batboy turned team official. Mantle’s former driver, Mark Dymond, was once walking with the Mick toward an elevator at a Florida fantasy camp when a boy of about eleven years of age approached.

  “Mr. Mantle, can I have your autograph?” the kid asked.

  “Fuck off,” Mantle barked.

  Jeter was leaving no such trail of shocked, heartbroken worshipers. “And I like that as a friend of his,” Tino Martinez said, “because I’ve been with other players who rejected people in restaurants, and you go, ‘Oh, man.’ It brings you down. With Derek it’s always just a matter of when he’ll sign. He’ll sign for the entire restaurant if they want, the cooks, the waiters, everybody.”

  As it was, Jeter often chose to stay in and watch movies. When he did go out he preferred clubs with roped-off areas for VIPs in search of a little distance and peace. His brushes with troublemakers were kept to a minimum, but his fame, fortune, and team affiliation made some incidents unavoidable.

  During his early years with the Yanks, Jeter was out with Martinez when approached by a nervous stranger who kept asking him, “Do you have any candy? Do you have any candy?”

  “No, but I’ve got some gum,” Jeter responded. Martinez had to inform his teammate the man wasn’t looking for M&M’s, but drugs.

  “In Boston, first three or four years of Derek’s career,” Martinez said, “no matter where we went guys would get loud and shout, ‘Nomar’s better than you. Nomar’s the man.’

  “They were always trying to get Derek fired up and say, ‘Go fuck yourself,’ but he wouldn’t do it. Derek would just say, ‘Hey, you’re right. It’s cool. Nomar’s a great player.’ And it would defuse the situation.”

  Jeter had a way of minimizing the chances of a confrontation. Jorge Posada, his close friend, marveled over the way the shortstop could apply the same instincts that framed his flip play in Oakland to a crowded nightclub.

  “He’s always looking around,” Posada said. “He knows if that lady’s standing right there and she looks, he knows that lady’s coming about ten, fifteen minutes later to either say hello or do something. He sees the whole room. He’s unbelievable, how he can scan out people and really read them.

  “We’ll be out and there will be a situation that puts us in a spot, and he’ll know to take off right away. He analyzes things before they happen, which is what he does on the field.”

  Sometimes Jeter would cause a problem just by showing up in a restaurant. Martinez was a dinner partner of Jeter’s at times when roomfuls of women were angering their boyfrien
ds and husbands by staring at the shortstop.

  “You hear their comments, and you know they’ve had a few drinks,” Martinez said. “Derek’s not looking at the girls, it’s not his fault, but I’d just tell him, ‘It’s not good here. Let’s get out of here.’”

  Not that the shortstop spent his off-field life fleeing the advances of attractive women. Jeter thoroughly enjoyed the spoils of his looks and stardom when it came to the opposite sex, though he was careful to avoid women he felt were more interested in his celebrity standing than they were in him.

  Jeter’s mother and sister reviewed the candidates, and they represented a tough judge and jury. “Divorce is not an option,” Sharlee would say. “We have those traditional values that, you get married, you’re in it for the long haul . . . [Derek] keeps saying, ‘I’ve got to be with a girl for five years before I marry her. I’ve got to make sure this is the one.’

  “Our parents are still madly in love with each other after all these years, and that’s how we want it to be. So we’re not going to marry the first person that we think is great, and oh, if it doesn’t work there’s always a way to get out of it. That’s not an option for us.”

  With the stakes so high, Jeter did not rely solely on his sister and mother. If he thought a relationship was possible, he would run his girlfriends through a quiz that resembled the one Eddie gives his fiancée, Elyse, in the classic scene in the movie Diner.

  Only Jeter would not ask his date/contestant about the Baltimore Colts, or the New York Yankees for that matter. He would pose hypothetical, what-would-you-do-in-this-situation questions to get a read on a woman’s moral compass. “It’s usually about how she would handle a certain situation,” Jeter’s friend and former teammate Gerald Williams would say. “He’s trying to find out if she would lose her cool and rant and rave, or stay calm and keep her dignity. He’s not looking for someone who exhibits extreme behavior. . . .”

  Mariah Carey passed a few of these tests along the way but flunked the final exam. “She was much more boisterous than Derek wanted,” said one Yankee official. “He likes women in the background, and she was the opposite.”

  Jeter was not receptive to aggressive come-ons, whether the aggressors were female fans running onto the field—one would race out to Jeter at short to hand him her phone number—or supermodels gracing the covers of the most prominent fashion magazines. “I’ve seen a supermodel at the top of her game try to get to Derek,” R. D. Long said, “and it never happened. Just how she tried to do it didn’t work for him.”

  Enough women were smart enough, conservative enough, and classy enough to catch Jeter’s eye, win his affections, and contribute to his standing as a ladies’ man extraordinaire. Teammates who were close enough to Jeter to get away with it occasionally teased him about the parade of women forever marching his way.

  Bernie Williams watched music videos with Jeter in the players’ lounge, and whenever an attractive singer or dancer appeared on screen, the center fielder pushed the shortstop’s buttons.

  “Do you know that girl?” Williams would ask. “I know you know that girl.” Sometimes Jeter would confess he did.

  In his dealings with the news media, Jeter reacted to questions about his personal life the way he would react to a four-strikeout day at the plate. He occasionally showed up with a girlfriend courtside at Madison Square Garden for a Knicks game, but he did what he could to prevent photographers from the Daily News and Post to provide a running visual commentary on his love interests in their gossip pages.

  “If he’s dating a girl,” Martinez said, “it’s dinner and a movie, and no drinking until four in the morning. Maybe when you win the World Series, but other than that, no.

  “I mean, he’s a normal guy, and the girls he dates usually are pretty normal. And when they’re not, or they want the big party scene, then they’re gone.”

  Discretion was of utmost importance to the shortstop. One woman who briefly dated Jeter would tell a story of the time she and a girlfriend were invited to the shortstop’s home for a small party. Jeter answered the door and politely asked his guests to remove any cell phones or cameras they were carrying and place them on a table, explaining that he wanted to protect his privacy.

  When out in a club, Jeter would often ask a wingman, teammate, or staffer to approach a woman he would like to meet and extend an invitation on his behalf. If Jeter and the woman were interested in taking the evening elsewhere, they would often leave separately, through different doors. Sometimes Jeter would leave a club in a separate car while his driver transported the woman to their next meeting place.

  Image wasn’t everything, despite Andre Agassi’s claim to the contrary in the Canon ad, but it still meant a lot even to a ballplayer defined by his substance-over-style core. One late night on a West Coast trip, a witness spotted Jeter pulling up to the team hotel in a cab with two female passengers. The witness stayed in the shadows and watched the scene unfold.

  Jeter emerged from the cab first and made his way to the hotel elevators. A few minutes later, one female passenger stepped out and followed in Jeter’s footsteps. A few minutes after that, the second female passenger stepped out and took the very same path.

  It did not matter whether these women were Jeter’s dates, or his friends, or his Scrabble partners looking for a game at 3:00 a.m. What mattered was his concern over appearances, even in the middle of the night.

  Jeter never made a mistake in public, and there was a good reason why. From the spring training fields of Florida to the big league hotels of California, Jeter never forgot Don Mattingly’s warning the day the veteran first baseman told the kid shortstop to run it in:

  You never know who’s watching.

  Derek Jeter knew 2002 would be a different season even before Ruben Rivera, Mariano’s cousin, was literally caught stealing one day in March—stealing a glove and bat from Jeter’s locker.

  Once regarded as a Mantle-like prospect, Ruben had a deal to sell the items to a memorabilia dealer for $2,500, a curious move for an outfielder with a million-dollar wage. “A rookie mistake,” Ruben called it, even though his rookie season had come and gone six years earlier.

  “He had six or seven gloves; I didn’t know he would be that mad,” Rivera would explain. Oh, Jeter was mad. “I have no comment on the whole situation,” the shortstop said. “There’s no need to add fuel to the fire.”

  That fire was an inferno. Jeter often sold his game-used bats and gear through Steiner Sports Memorabilia and committed more than $250,000 a year in proceeds to his Turn 2 Foundation and its programs designed to keep kids drug- and alcohol-free.

  But Jeter never sold his gloves. “I know those gloves are very personal,” said the head of the memorabilia company, Brandon Steiner.

  Only this wasn’t just about the glove, among Jeter’s favorites. His space and his standing as unofficial team captain had been violated.

  Rivera was released by the Yankees, who likely would have released Mariano’s cousin even if he had swiped the glove belonging to the twenty-fifth man on the roster. But with Jeter as the victim, Rivera’s admission and apology never stood a chance. Brian Cashman agreed to a $200,000 settlement on Rivera’s contract and bid the disgraced Yankee farewell.

  This was still very much Jeter’s team, even if George Steinbrenner had given Jason Giambi a seven-year, $120 million deal to restore the Yankee offense to a championship level (and allowed clubhouse access to the Oakland slugger’s personal trainer, Bob Alejo). Giambi was given the full news conference treatment on arrival—as opposed to Jeter’s quickie conference call announcing his $189 million deal— and was fully expected to use Yankee Stadium’s inviting right-field porch to match or surpass his 38-homer, 120-RBI final season with the A’s.

  Giambi had shaved his goatee and cut his biker-boy hair in accordance with Steinbrenner’s clean-cut mandates, and he picked number 25 because the digits added up to 7, the number worn by the Mick, his father’s favorite player.

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��I know I’m replacing a great Yankee,” Giambi said of Tino Martinez, who had replaced a great Yankee in Don Mattingly. Martinez understood the lure of Giambi’s league-leading .477 on-base percentage and .660 slugging percentage, but he was wounded by the fact that the Yanks did not re-sign him after a 34-homer, 113-RBI season, and by the fact that Roger Clemens was among the teammates who helped recruit Giambi.

  Jeter was the one prominent Yankee who made it clear he would not help the team replace his friend, who wound up in St. Louis. “He was the only one who wasn’t afraid to stand up,” Martinez said.

  No, Jeter was not afraid to make a stand for a friend. But when it came to social or political issues, even those directly related to the business of baseball, Jeter defaulted to the Michael Jordan, Republicans-buy-sneakers-too approach.

  In May of 2002, if soaring home-run totals and bulging biceps had not already made it clear baseball had a major steroids problem, Ken Caminiti stamped the plague official in an explosive interview with Sports Illustrated’s Tom Verducci. Caminiti acknowledged having used steroids when he won the National League’s Most Valuable Player award for the Padres in 1996 and said of his sport: “It’s no secret what’s going on in baseball. At least half the guys are using steroids. They talk about it. They joke about it with each other.”

  Jose Canseco would put the number of steroid users at 85 percent. “There would be no baseball left if they drug-tested everyone today,” Canseco said.

  At the time 50 percent appeared to be the more credible figure, and one approved by the likes of Curt Schilling. Some players were adding thirty to forty pounds of muscle, and they were having trouble finding batting helmets to fit their swelling heads.

  Steroids represented a legitimate health crisis in America, as young athletes were in the habit of imitating their big league heroes. Mark McGwire’s admission of androstenedione use in ’98 inspired so many teens to buy andro, a steroid precursor, that fitness stores could not keep it in stock.