The Captain: The Journey of Derek Jeter

by Ian O'Connor

  Only the final score in this hotel conference room in Tampa resonated on the ball field in the Bronx: Derek Jeter did not lose. Even when his own mighty Yankees were in the opposing dugout, Jeter found a way to win. Arbitrators Ira Jaffe, Gil Vernon, and Nicholas Zumas decreed the Yankee shortstop was most deserving of a $5 million wage.

  In the days to come, Jeter would receive a stack of letters at his spring training locker congratulating him for winning the case. “Kind of overwhelming,” the shortstop said.

  He would playfully shout to Bernie Williams, “When will you buy me dinner? How does it feel to make $87 million?” and Williams would warn the Yankees that they had better sign Jeter to a long-term deal before his price made Bernie’s $87.5 million contract look like a 20 percent tip.

  Meanwhile, Jeter’s arbitration triumph sent seismic waves crackling across the baseball landscape, leaving every major league executive cowering under his or her desk. Every major league executive but one: George Steinbrenner, owner of the New York Yankees.

  Steinbrenner was red with rage. “I would say he is happy for Derek and disappointed in me,” said Cashman, who would describe the Boss as “clearly upset.”

  Steinbrenner did not completely denigrate Cashman publicly, not when the winner here was everybody’s all-American boy, Derek Jeter. “He is young and he is learning,” Steinbrenner said of his GM. “I hope he has learned a lesson. . . . I hope it’s the only thing I lose this year.”

  The Boss was hoping against hope. In the immediate wake of his loss to Jeter and Close, Cashman went down swinging against his closer, Rivera, who won an arbitration judgment of $4.25 million against the team’s bid of $3 million. As was the case before the Jeter hearing, the player’s agent approached Cashman with a settlement offer, this time at $3.9 million.

  The GM had just cost Steinbrenner $900,000 by rejecting Close’s compromise figure, and he could not afford to go 0 for 2. Cashman could have played it safe, agreed to pay Rivera $3.9 million, and stayed out of harm’s way.

  But rather than follow his survivor’s instinct, Cashman followed his heart and head. He decided there would be no deal.

  Cashman guessed wrong again, leaving the Yankees as the only franchise to lose in the first eight arbitration cases that were heard. By refusing to settle on Jeter and Rivera, Cashman cost his company a combined $1.25 million in the two hearings. “These were two costly decisions,” he agreed.

  They would not be costly just for Steinbrenner; they would be costly for Cashman, too. The Boss blistered him for losing both ends of this double-header and decided Cashman needed to pick up a small part of the tab.

  “I got my World Series bonus pulled, fifty grand,” Cashman said. “I didn’t think it was fair, but that’s life. That’s working for George. Losing bothers him, and so does being taken advantage of. If he goes to a basketball game and he thinks his seat sucks, that’s losing to him, and he doesn’t like it.”

  Steinbrenner lost to Rivera after he had lost to Jeter, so Cashman would be his personal piñata for some time. Never mind that the Rivera defeat came on the same day Cashman executed only the second-biggest trade in franchise history, right behind the $100,000 purchase of Babe Ruth.

  The GM had put together a megadeal with the Toronto Blue Jays that required a full meeting of Steinbrenner’s cabinet. The Boss gathered his top officials at his favorite Tampa restaurant, Malio’s, and asked them to vote on the proposal Cashman had before him: David “Boomer” Wells, Graeme Lloyd, and Homer Bush to Toronto for Roger Clemens.

  Clemens was quite possibly the greatest pitcher of his generation and an ace Steinbrenner had been courting for years, even lifting weights with the Rocket during a recruiting visit at his home. The Boss wanted him badly, but he had built a friendship with the free-spirited Wells that compelled him to abstain from the vote.

  It was unanimous—Clemens was a Yankee. “We’ve got a group of warriors here and we’re getting a very big warrior,” Steinbrenner would say. “He’s a monster.”

  But the Yankees were a monster team in ’98, and Wells had a talent as large as his gut. If the left-hander could be a high-maintenance ass, facts were facts: he was 34-14 for the Yankees, 5-0 in the postseason, and he had pitched a perfect game. Yankee fans loved him the way golf fans loved John Daly—for his Everyman body and Joe Six Pack act.

  Wells had a Ruthian appetite for New York; he loved appearing on the sets of Late Show with David Letterman and Saturday Night Live. He had big plans for spending the balance of his prime bouncing from one Manhattan nightspot to the next, at least until Joe Torre—never a Wells supporter—summoned him into his office the first morning of spring training.

  “I’m in the principal’s office already,” Wells said on the way in.

  He had no idea he was seconds away from being expelled.

  Wells retreated to his Tampa home, where David Cone found him to be inconsolable over a four-hour visit. “I’ve never seen anyone so stunned by a trade,” Cone said.

  It was one the Yankees had to make. When Cashman had heard what Toronto GM Gord Ash wanted in exchange for Clemens, “my knees buckled,” he said. In a good way. The Yankees did not want to tinker with the karma of ’98, but this was Roger Clemens, the only five-time Cy Young Award winner in the history of the game.

  “We’re acquiring the Michael Jordan of pitchers,” Cashman said.

  “Christmas in February,” Torre called the occasion.

  “I finally got you,” the Boss told the Rocket. Nobody knew it at the time, but George Steinbrenner did not only land a pitcher who wanted to win his first championship ring as desperately as the owner wanted to win his fifth.

  Steinbrenner also acquired the one player he would ultimately consider a rival to Derek Jeter for the most prestigious position in sports: captain of the New York Yankees.

  When the 1999 Yankees pulled into Seattle in early August, they did so without the same aura of invincibility their predecessors wore as easily as they did their interlocking “NY.” They were 64-42 and up six games in the American League East, as opposed to 78-28 with a fifteen-game lead the year before.

  It had been a turbulent time for the Yankee family, starting with Joe Torre’s shocking disclosure in March that he had prostate cancer and was leaving the team to treat it. Two days after Joe DiMaggio died from the effects of lung cancer, and the same day Darryl Strawberry sat in a spring training dugout to talk about his return from colon cancer, the Yankees addressed their fifty-eight-year-old manager’s head-on collision with his own mortality.

  “From what I understand,” Derek Jeter said of Torre’s illness, “it is a good cancer to have. There’s no good cancer, but it is the best to have.”

  The shortstop had never met a negative he could not convert into a positive. But truth was, the news crushed Jeter, the Yankee closest to Torre.

  “He gave me the opportunity my first year,” Jeter said. “I didn’t play well in the spring and he said it was my job. He doesn’t embarrass you. He is one of the reasons I am here today.”

  Jeter’s team had lost its rock, and grim bulletins were coming in from all over Yankeedom. Catfish Hunter was suffering from Lou Gehrig’s disease. Mike Lowell, the likable Yankee prospect just traded to the Marlins, had been diagnosed with testicular cancer.

  Chuck Knoblauch’s father was suffering from Alzheimer’s disease. On the day the news broke about Torre, Scott Brosius’s father, Maury, would tell a reporter that his colon cancer had returned, that the doctors said he could not beat it, and that he would prefer this news not be printed before he could tell his son he was dying.

  The ballpark was the Yankees’ sanctuary, their place to hide. The games had to go on, and Don Zimmer, a sixty-eight-year-old bench coach with a bum knee, was the man chosen to take Torre’s place until the manager returned from surgery.

  Hopelessly overmatched, Zimmer waged a public battle with Steinbrenner over how he was using Hideki Irabu, whom the owner had called a “fat, pussy toad” after Ira
bu failed to cover first base in the spring. Zimmer mercifully handed back the team to Torre on May 18 in Boston, where the Yankees’ manager returned early to a most unexpected series of sights and sounds: the Fenway Park crowd gave him a standing ovation when he walked the lineup card to the plate.

  The Yankees became the Yankees again in the summer, even if Clemens could not get comfortable in his pinstriped skin. Teams still had a certain fear of the ’99 Yankees—even if they were more vulnerable than the ’98 team—and that respect was obvious as far back as the April 5 opener in Oakland, where rain stopped play after eight innings with the A’s holding a 5–3 lead.

  “Everybody was praying we wouldn’t restart that game,” A’s general manager Billy Beane said. “The Yankees only had three outs left, and everybody in that stadium, including the general manager of the A’s, thought the only way we were winning that game was if Mother Nature intervened.”

  The Yanks recovered from that rain-shortened defeat. Like Wells the year before, Cone would pitch a perfect game, this one against the Expos with Don Larsen and Yogi Berra in the house. (Larsen and Berra were celebrating Yogi Berra Day; the Hall of Fame catcher had finally ended his feud with George Steinbrenner and agreed to return to Yankee Stadium for the first time since his 1985 firing.)

  Cone knew how to mark the occasion. “At that point we’re thinking, ‘We got our hands around the throat of a dynasty now,’” the pitcher said. “That’s the first time that word started to creep in.”

  Cashman acquired David Justice from Cleveland at the end of June, and Steinbrenner decided against dealing Andy Pettitte at the end of July, a reprieve that helped Pettitte remember how to get batters out. The Yankees opened up another comfortable divisional lead and did so without Strawberry, the recovering cancer victim who had been suspended for violating his aftercare program following his April arrest for soliciting a prostitute and possessing cocaine.

  Strawberry had lectured Jeter on staying out of trouble, on avoiding the temptations that had consumed much of Strawberry’s career, and to date the young Yankee had listened times ten. Just as the cloud of suspicion started hovering over baseball’s home-run heroes—Mark McGwire had admitted the previous summer to using androstenedione, a steroid precursor, during his record homer barrage—Jeter had established himself as a pure, stain-free winner.

  The only problem Jeter had caused anyone in baseball? He made it impossible for Little League coaches across America, especially in the New York area, to pick through the countless requests for jersey number 2 to find the kid who deserved the lucky bounce.

  Jeter played the game like a boy, so boys wanted to play the game like Jeter. Right-handed kids were delaying games on ball fields in every time zone, taking that slow and familiar bowlegged approach into the batter’s box.

  They would stick their bat under their left armpit and readjust their batting gloves like Jeter. They would plant their right foot on the back line of the box and keep their left foot out like Jeter. They would swing their left foot into the box, drop their head toward the dirt, and stick their extended right hand toward the umpire—as if trying to put that umpire in a trance—until they were ready like Jeter.

  They would look up at the pitcher and start waggling that bat like Jeter. Chances were, they would not keep their hands inside the ball like Jeter.

  While taking infield practice, Little Leaguers with dreams bigger than Williamsport would try Jeter’s signature play at short—the running backhand in the hole, followed by a plant of the left foot in the outfield grass, a Jordan-esque jump for the sky, and a Baryshnikov pirouette in midair while releasing a powerful throw to first.

  It did not matter if the boys weren’t strong enough to swing their left shoulder against their midair momentum and reach first base on the follow-through—their attempts paid tribute to the way Jeter honored the game. He ran out every ground ball. He never berated an umpire. He never betrayed the DiMaggio way of giving his all—regardless of score or circumstance—because there might be someone in the stands who had never seen him play.

  Jeter lived a simple, graceful life. He ironed his own clothes and picked up his own dry cleaning. He did half-hour morning workouts in his apartment building’s gym before leaving for the Stadium. He got his hair cut, in his apartment, by a friend named Mike Daddy. He ate lunch with his friend Sean Twitty and made daily pregame stops at Starbucks.

  By August of 1999, Jeter was more than a role model and a complete ballplayer. He was a coveted product spokesman, too.

  His long, broad face was becoming synonymous with class, virtue, and victory. Jeter was as perfect for the role of athlete endorser as the founding father, Arnold Palmer, as perfect as Michael Jordan was when the sneaker company explosion changed professional and major college sports.

  Untouched by scandal or controversy, Jeter was handsome, clean-cut, and quick to sign an autograph. Almost as a bonus, the likes of established veteran Paul O’Neill were saying Jeter was the best ballplayer they had ever played with.

  He was already being mentioned as a future captain of the Yankees. He dated supermodels at night and helped their grandmothers cross the street by day.

  The city loved Jeter, and Jeter loved the city right back. Much like John F. Kennedy Jr., he moved about town with an elegant and dignified step.

  Jeter and JFK Jr. were not rival princes for any throne, but after JFK Jr. perished in a July plane crash, a death that stunned and saddened Jeter and millions of fellow Kennedy admirers, R. D. Long turned to his friend as they were sitting in the shortstop’s apartment and declared, “You are now the king of New York.”

  Jeter was not trying to ascend to this throne, and he certainly did not want to land there by way of a tragic turn of events. “But he knew it was something he wasn’t going to be able to escape,” Long said. “He assumed the role without claiming it.”

  If he was not the crowned king of New York, Jeter was at least the blossoming prince of Madison Avenue. He had endorsement deals with Nike, Coach leather products, Skippy peanut butter, Florsheim Shoes, the Discover Card, Fleet Bank, and Acclaim Entertainment, and he asked all of his corporate benefactors to get involved with his Turn 2 Foundation initiative to keep kids off drugs. Michael Jordan recruited him to be part of his brand and to be the only baseball player featured in a commercial starring Jordan’s handpicked stable of athletes, one that included Roy Jones, Ray Allen, and Randy Moss.

  Jeter turned down endorsement opportunities every week to avoid overexposure, to align himself only with companies he felt matched up with his image, and, of greatest consequence, to keep his focus on winning championships.

  His was a life of substance over style, of dependability over drama. “Derek was the most low-maintenance star I’ve ever been around,” said the Yankees’ PR man, Rick Cerrone. “He never told us he wouldn’t do something, he had no entourage, he had no special interview rules. People loved him as a baseball superstar, and women loved him as a sex symbol, but he never carried himself like that.”

  Cerrone received a nonstop supply of requests from parents of sick children who wanted to meet Jeter, and the shortstop met as many of those children as he possibly could. He did not offer kids a signed ball and a pat on the cap on his way to the batting cage. Jeter forever took the time to make meaningful eye contact with the boys and girls, to engage them in conversation, to give them his batting gloves, and to introduce himself to emotional mothers and fathers he addressed as “ma’am” and “sir.”

  “It was like the Walt Disney thing, plussing the experience,” Cerrone said. “Derek Jeter always plussed the experience.”

  So on the night of August 6, 1999, Jeter arrived at Seattle’s Safeco Field—the Kingdome’s successor—as an unblemished and unchallenged baseball star. He was batting .352 with a career-high 20 homers, obliterating his employer’s arbitration claims that he could barely get the ball out of the infield.

  Jeter was not happy when he received the news that Joe Torre was giving him
a rest; the manager thought it was a good time for a break after his shortstop had been hit on the left wrist by a Jose Paniagua pitch the previous night. But Jeter settled in and watched as his first-place Yankees carried an 11–5 lead into the bottom of the eighth.

  Alex Rodriguez launched a three-run homer off Jason Grimsley to make the game interesting, just not nearly as interesting as Grimsley made it when he hit Edgar Martinez in the side two pitches later, one pitch after sailing a fastball over his head.

  Grimsley was ejected by home plate umpire Gary Cederstrom, and the Yankees knew what was coming in the top of the ninth, the inevitable retribution putting their dugout on edge. Frankie Rodriguez had recently touched off a Dodger Stadium brawl by throwing at Mark Grudzielanek’s head, and he was staying in the game to start the ninth as Jose Mesa warmed up in the pen.

  Luis Sojo’s at-bat came and went quickly without incident—he was retired on the first pitch. But baseball’s code of frontier justice would have spared Sojo during a longer stay at the plate anyway, as he did not have the resumé or skill set required in the eye-for-an-eye tradeoff Seattle was seeking.

  Martinez was a career .300-plus hitter coming off four consecutive 100-plus RBI seasons, and Rodriguez was not about to drill the ninth batter in the Yankee order, Sojo, who was only in the lineup to give the sore Jeter a rest.

  But the leadoff hitter, Chuck Knoblauch? Now he was a worthy target, and everyone in both dugouts realized it. So on the second pitch, Rodriguez did what baseball’s unwritten law told him to do. He threw a fastball that glanced off Knoblauch’s rump.

  Had Cederstrom ejected the Mariners’ reliever right then and there, tempers might have cooled and both teams might have called it a draw and moved on. When Cederstrom did not eject Rodriguez the way he had ejected Grimsley, the Yankees started screaming at the pitcher and the ump.

  Rodriguez shouted back as he left the field—Lou Piniella had taken him out of the game—and Joe Girardi, the on-deck batter, returned verbal fire, compelling Rodriguez to throw down his glove and charge the Yankee catcher.