The Captain: The Journey of Derek Jeter

by Ian O'Connor

  So Derek dumped her. In fact, the dumping was decisive enough to give birth to a new street verb—Jeter. To “Jeter” someone suddenly meant to break up with a girlfriend or boyfriend in an abrupt and don’t-even-think-about-getting-back-together way.

  Mariah would be reportedly “Jetered” after the season, when the Daily News said she approached her ex at Sean “Puffy” Combs’s party at Cipriani on Wall Street and flirted away, only to have the shortstop turn his back on her.

  But Jeter did not say a single bad word about Carey and her high-maintenance ways, even if he was baited by his old friend R. D. Long.

  “I’d be telling him, ‘I told you, it’s just a matter of time before she pissed you off . . . ,’” Long said. “He’d say, ‘Oh, man, she’s all right, man. She’s OK.’ . . . That’s Derek. He wouldn’t bash her. He doesn’t bash anybody. I told him, ‘You’ve got to find a girl who’s grounded,’ and he wouldn’t criticize her.”

  Jeter was not terribly enthused about the aggressive photographers who tracked them, or the opposing fans who chanted Mariah’s name, or the stadium operators who played Mariah’s songs when he stepped to the plate on the road. Jeter would confess he could not adjust to the relentless attention he received as Mariah Carey’s boyfriend. “It didn’t bother her the way it bothered me,” he would say.

  In the book he would write with Jack Curry, The Life You Imagine, Jeter would also say the Carey relationship taught him it “would be very difficult for me to seriously date a high-profile person.” Over time Jeter would defy his own words by courting an endless procession of starlets and supermodels.

  But baseball was his first love, and Jeter was playing it as a precious few could. He lost the batting title to Bernie Williams over the final two weeks of the season as he swung for the fences in his failed pursuit of his twentieth homer, yet Jeter’s .324 average was still a point better than Nomar Garciaparra’s and 14 points better than Alex Rodriguez’s.

  He stole 30 bases, led the AL with 127 runs, and became the only Yankee shortstop not named Phil Rizzuto to collect at least 200 hits in a single season. Jeter had scored more runs in his first three full seasons (347) than any shortstop before him, and he would finish third in the league MVP voting.

  On the other side of the ball, Jeter committed only 9 errors in 625 chances, a long, long way from his 56 errors in 506 chances in Greensboro five years earlier. His Yankees finished 114-48, the most victories in AL history. Their .704 winning percentage was the best in baseball since the 1954 Cleveland Indians won at a .721 clip (111-43).

  The summer belonged to McGwire’s 70 homers and to Sosa’s 66, both sums mocking the standard of 61 set by Maris in ’61. Only the sport would not be about the sluggers and their comic-book muscles in October.

  It would be about a team that did not dress a single 30-homer hitter, a team that could not afford to go out like those ’54 Indians, swept in the World Series by the New York Giants.

  After the Yankees’ 114th and final regular-season victory, George Steinbrenner marched into his clubhouse and announced he had been reading Cigars, Whiskey & Winning: Leadership Lessons from General Ulysses S. Grant.

  “We’re about ready to go to war,” Steinbrenner said. “And I love war.”

  His shortstop had a far less flamboyant way of declaring the same thing.

  “It makes no difference what we did in the regular season,” Derek Jeter said.

  On the night of October 13, in the sixth game of the American League Championship Series, Derek Jeter came to the plate in the eighth inning with a postseason batting average of .156.

  He had made a big defensive play on a broken-bat dribbler near the end of Game 1 of the Division Series sweep over Texas, a play David Wells said had saved the game. Jeter had also applied his leadership skills across the first five games of the ALCS matchup with Cleveland. He had reassured his friend Chuck Knoblauch, after he had committed an embarrassing mental error in the twelfth inning of the Game 2 loss (Knoblauch blew his gum into a bubble and argued with an ump rather than chase a loose ball near first base), and he had relaxed a drum-tight Joe Torre before Game 4.

  “Derek came walking down the dugout,” said Torre’s bench coach, Don Zimmer, “and sticks a finger in [Torre’s] chest and says, ‘Mr. Torre, you know this is the most important game in your life.’ And everybody cracked up.”

  Down 2–1 to the Indians, still feeling the weight of a 114-win regular season and an overbearing owner terrified of losing again to his hometown team, Torre was bailed out by El Duque Hernandez in Game 4 and by David Wells in Game 5.

  Back in the Bronx for Game 6, Torre felt good about having 20-game winner David Cone on the mound protecting a 6–0 lead in the fifth. But just like that, Cone walked in a run and Jim Thome blasted a grand slam, sending a tense night and a tense series reeling toward who knew where.

  The next inning, Jeter’s counterpart at short, the great Omar Vizquel, threw high to first and committed his first error in 47 postseason games and 237 postseason chances. Two batters later, with two on and one out, Jeter was a welcome sight to Cleveland reliever Dave Burba.

  Jeter was 5 for 32 in the playoffs, 1 for 14 in his previous four games. In nine regular-season and postseason at-bats against Burba, Jeter had three strikeouts and one infield hit and had failed to put a single fair ball in the air. But on Burba’s first pitch to the shortstop on this night, Jeter loosed that inside-out swing of his and sent a deep fly to right field that would inspire another wild, crazy, and prosperous result.

  No twelve-year-old boy would define this play, just a right fielder who preferred to act like one. Manny Ramirez raced for the wall, turned his back to the ball, and never again tracked its flight. Instead Ramirez planted his spikes into the blue padding and began his dramatic, breathless climb while Jeter’s shot hit the base of the wall about five feet to his left.

  As the full Yankee Stadium house exploded, Jeter raced all the way to third. Two runs were in, the home team had an 8–5 lead, and the Indians would be left to listen to the crowd chant “1948”—their last championship season. Jeter robbed Travis Fryman on a grounder up the middle in the eighth, and Mariano Rivera finished off Cleveland on Vizquel’s grounder back to the mound in the ninth.

  The 1998 Yanks had exorcised a 1997 haunt. “It’s like getting a knife stuck in your heart,” Vizquel said afterward. “Your body goes stone cold.”

  On the winning side of the Bronx, only the champagne was stone cold. The Yanks’ celebration was tempered only by the fact that Darryl Strawberry was not part of it; Strawberry was resting inside Columbia-Presbyterian after undergoing surgery to remove a cancerous tumor in his colon.

  When players were not in the trainer’s room talking to Strawberry on the phone, they were dousing each other in the clubhouse and trying to stay clear of George Steinbrenner, who was conducting interviews in the middle of the room. Jeter spotted the owner and made a move only he could get away with.

  “Hold on, hold on,” the shortstop shouted as he headed toward the bone-dry Boss. “Oh, Boss Man. Somebody’s dry around here.”

  With that Jeter poured a bottle of champagne over his employer’s head. Steinbrenner laughed and asked for someone to get him a towel. His eyes blinded by the sweetest sting, the Boss barked, “Where is that Jeter?”

  On his way to another World Series parade.

  As it turned out, the San Diego Padres were accidental tourists in the Fall Classic, arriving in New York as the ultimate just-happy-to-be-here props. Jeter hit a Game 1 single that helped set up Tino Martinez’s deciding grand slam off Mark Langston—with a little help from plate umpire Rich Garcia, he of Jeffrey Maier fame, on a 2-2 pitch that should have been ruled a strike—and the Padres just about folded on command.

  Scott Brosius delivered the crushing three-run blow against Trevor Hoffman in Game 3, silencing Qualcomm Stadium and, ultimately, nailing down the MVP award. Jeter singled and scored what would be the championship-clinching run in Game 4—of course he
did. He also worked an eighth-inning walk and scored the second run in a 3–0 victory that gave the Yankees their twenty-fourth World Series title and a staggering 125 victories in all.

  Steinbrenner had been in talks to sell the Yankees to Cablevision in a potential deal that would allow him to maintain some control over the team, but suddenly he was not so eager to relinquish the brand that had made him an American titan.

  Even before the first Game 4 pitch was thrown, Steinbrenner suspended all of his nagging superstitions, his maddening fear of jinxes, to answer a reporter’s phone call and announce the following: “I think you have to say it now. Twenty years from now, people will look back on this team as truly the greatest of all time.”

  No team had ever won 125 games. “I don’t see how you can say we aren’t the greatest team ever,” Jeter said when the sweep was complete. No, Steinbrenner wasn’t letting go of that.

  In the bowels of Qualcomm, the Yankees enjoyed yet another champagne bath, and Jeter—who hit .353 in the World Series—enjoyed yet another chance to dump a bottle of bubbly over Steinbrenner’s head. With the owner’s familiar blue blazer and white turtleneck drenched in the victor’s spoils, Steinbrenner joked that his shortstop was the only Yankee who could survive such a fireable offense.

  They took a 2,800-mile victory flight home, rode in another war hero’s parade, and gathered for another City Hall ceremony. Jeter led the league in marriage proposals one more time.

  “I don’t think there’s a person in the world who’s been more spoiled than I’ve been,” he said at the ceremony.

  Better yet, Jeter’s luck wasn’t about to turn. He was just starting a dizzying run of on- and off-field successes, one that would make him the DiMaggio and Mantle of his time.

  7. Dynasty

  Derek Jeter sat on one side of the table, and his employer sat on the other. The shortstop and the team were much like the New York Yankees and Boston Red Sox—clearly defined enemies prepared to bludgeon each other over a singular prize.

  Only this was not the American League pennant at stake, just a ballplayer’s pot of gold. Jeter wanted to be paid $5 million for the 1999 season, and Yankees general manager Brian Cashman wanted Jeter to be paid $3.2 million for the 1999 season.

  Either way, Jeter understood he could not lose. He was going to make more to play one year of baseball than one of his heroes, Sonny Connors, had made in a lifetime of hard labor.

  At sixty-eight, Connors had died of a heart attack in January, devastating his famous grandson. Sonny was the head of maintenance at Queen of Peace in North Arlington, New Jersey, for thirty-six years, and he was so beloved in the parish that the schools were closed for his funeral.

  Jeter was a pallbearer and one of nearly a thousand mourners who attended the service. At the end of the Mass, as the casket was taken out of the church, Connors inspired the kind of standing ovation often reserved for his grandson.

  “I’ve been a priest for fifty years,” the Queen of Peace pastor, Thomas Madden, would say, “and that’s the only time I’ve ever heard that kind of applause. It gave you chills. It was like we were honoring a saint.”

  Sonny was a saint to the Jeters. Derek marveled over his grandfather’s refusal to call in sick, over Sonny’s insistence that he show up for work regardless of circumstance. Connors was the model for Derek’s own relentless commitment to his job.

  “He didn’t make millions,” Jeter said in his clubhouse, “but he affected as many lives as anyone in this room.”

  Connors died with a salary of $50,000, and his grandson was hardly in the mood to fight his employer over millions of dollars. But the system said Jeter had little choice, so fight his employer he did.

  They gathered in a hotel conference room in Tampa to hash it out before a panel of three arbitrators, and deep into this four-hour hearing Cashman knew he might be in a bit of trouble. An attractive attorney on the Yankees’ side of the table confided she could not stop staring at Jeter.

  If a member of the prosecution team was melting in Jeter’s presence, Cashman figured the judges would do the same. He had seen ballplayers use their charms before, especially in the 1994 case involving a first baseman with movie star looks, Kevin Maas, who gave an autograph to an arbitrator while mentioning he had to rush to the airport to return to a pregnant wife who was almost due.

  “That bothered me,” Cashman said.

  The Yankees won the case, but that did not make the process any more enjoyable. Arbitration was about as fun as a daylong trip to a proctologist’s office, as it pitted organization against athlete and often fractured otherwise healthy relationships beyond repair.

  For the first three years of a player’s big league career, the team held the hammer and the ability to renew a contract on its terms. The Yankees had been generous with Jeter and Mariano Rivera in their second and third seasons, paying them wages of $550,000 in ’97 and $750,000 in ’98 when they could have renewed them for plenty less. The team showed good faith in their homegrown shortstop and closer, critical pieces of two championship teams, and hoped the players would do the same when submitting arbitration bids in years four, five, and six and when negotiating free agent deals after that.

  But before their February ’99 showdowns with the Yankees, Rivera asked for $4.25 million in arbitration (the team offered to pay $3 million) and Jeter asked for a $4.25 million raise, or an award equaling the second highest in the sport’s history. Cashman did not believe his young stars were showing good faith, not after their agents promised the earlier generosity would be reciprocated down the road.

  So when Jeter’s agent, Casey Close, offered a midpoint settlement of $4.1 million before the hearing was about to start, Cashman shot him down. He was ready to trade heavyweight punches, and he was sure he would be the one walking out of the ring wearing the championship belt.

  Cashman and Close were arbitration newcomers, young, bright, and eager to establish something of a courtroom reputation. Close had been a good enough outfielder at the University of Michigan to bat .440 and hit 19 homers as a senior in 1986, to be named Baseball America’s College Player of the Year, and to get drafted and signed by a Yankees scout named Dick Groch, who also signed a future Michigan recruit named Derek Jeter.

  Close made it to Class AAA ball before ultimately becoming a big league agent with the International Management Group. Only a year on the job, the agent who negotiated Jeter’s post-draft deal with the Yankees, Steve Caruso, got a phone call from Charles Jeter explaining the family wanted to make a change.

  “And he said, ‘Here’s the deal. Dot’s good friend is Casey Close’s mom,’” Caruso said. “He felt it was a family thing, and I’m sure a part of it was you’ve got IMG as a billion-dollar business, and you’ve got Steve Caruso with a couple of employees.”

  Caruso did not lump in Close with the ethics-challenged agents he came to loathe; he thought his replacement had class. But if Caruso knew his firing would cost him some money, he had no idea how much.

  On February 15, 1999, Close was about to start showing him. He came to the table armed with claims that Jeter was an intangible genius and good citizen whose value to the Yankee franchise brand could not be measured by stats.

  Cashman figured Close was advancing a lost cause. Alex Rodriguez and Nomar Garciaparra were not even scheduled to earn a combined $5 million in ’99. Kansas City’s Johnny Damon was an arbitration loser “stuck” with a $2.1 million wage, and Cashman saw him as a comparable talent even though Jeter’s stats were superior and placed him third in the MVP race.

  The thirty-one-year-old general manager was in a tough spot. Jeter was sitting right there as the team’s heartbeat, the face of the franchise, and it was Cashman’s job to throw some heat right under his chin.

  So the GM started telling the arbitrators that Jeter was a great Yankee and clutch player and all-around wonderful guy, but that he was a ninety-eight-pound weakling, too. Never mind that Jeter had just set the team record for shortstops with 19 home runs
in ’98—A-Rod had smashed 42 and Garciaparra, 35.

  Left unspoken was the fact that A-Rod and Nomar were playing in hitter-friendly ballparks, while Jeter was shooting at a left-center wall 399 feet from the plate. As he sat across from this contained assault, oblivious to the attractive female attorney staring at him, Jeter died a thousand deaths.

  He was not a young man of many human weaknesses, but truth was, he was not any better at fielding criticism than he had been at fielding those minor league grounders in Greensboro.

  “I wouldn’t really say it was ugly,” said Jeter, “but no one wants to sit there and listen to a team tell you how bad you are. You think you’re doing a pretty good job and they tell you how bad you are.”

  Jeter understood that business was business, and that George Steinbrenner was not a wealthy man because he was in the habit of giving away his money. Jeter also saw how the team had fought Bernie Williams in free agency the previous fall, even agreeing to replace his bat with the one belonging to the vile Albert Belle before Belle reneged on a verbal agreement.

  Steinbrenner heard Bernie’s impassioned plea to remain a Yankee, and the owner agreed to give Williams $87.5 million to keep him away from the Red Sox. But both sides continued the marriage with fresh, permanent scars.

  Jeter had three more seasons to go before he reached free agency, so he had no choice but to listen to the Yankees tell an arbitration panel all about his alleged small-ball approach.

  “I need to hit some more home runs, it looks like,” Jeter said after the hearing was complete.

  “There’s no dispute about the player and the talent,” Cashman said. “It’s just what the deserved pay scale should be.”

  The following day, the verdict came in. Cashman felt the orgasmic rush of sure victory; the salary figures around baseball were all in his corner. Jeter was asking for the biggest wage ever for a player with three to four years of service time, and Cashman thought Close’s chief argument—his client’s mass appeal was priceless in the world’s biggest market—was one built to lose.