The Captain: The Journey of Derek Jeter

by Ian O'Connor

  Barely 160 pounds, Jeter was hopelessly overmatched by the velocity of the pitching and the speed of the game. He made critical errors at shortstop, went hitless in his first fourteen at-bats, and started ringing up monthly phone bills that would approach 400 bucks.

  “When you’re in high school,” Derek said, “you can’t wait to get out of the house, be on your own and away from your parents telling you what to do. When you’re down here, you realize you just can’t go back.”

  Jeter would step into the batter’s box and think about how many more hellish weeks he had to endure before he could go home. His games were played before a dozen fans, two dozen on a good day. Those games started under a blazing noontime sun so they would be over before the early-evening thunderstorms rolled in.

  For once in his life, Jeter yearned for the sleet and snow of a Kalamazoo spring. Gulf Coast League scores and standings were not printed in the paper. Jeter was stuck in a forgotten time and place, and he wanted his parents to save him. He wanted his girlfriend, Marisa Novara, to visit him. He wanted Bill Freehan, the Michigan coach, to reassure him.

  “Hang in there,” Freehan told Jeter. “It’s part of the process.”

  Derek could not help himself. The mind-numbing sameness of the routine—take early batting practice in the morning, grab something to eat, fail miserably in the game, stay for extra work in the evening, cry your eyes out at night—was wearing him to the nub.

  Suddenly the very word banned by his grandfather and mother—can’t—was the only word that rolled easily off his tongue. “The first few games,” Jeter said, “I was just swinging at everything. I didn’t have any idea where the ball was going.”

  Charles and Dot Jeter headed down to Tampa; Caruso had put a clause in Derek’s contract calling for the Yankees to fly in the shortstop’s parents at the team’s expense. Novara also made a trip.

  They told Derek the same things in person they had told him on the phone—everything would work out just fine. Charles reminded his son that an eighteen-year-old Chipper Jones hit .229 in rookie ball before hitting .326 the following season.

  At that point in time, Derek would have made any Faustian deal to hit .229, never mind .326. He was melting in the oppressive heat, wasting away to nothing, wishing every solitary hour of every solitary day he was a college Wolverine instead of a professional Yankee.

  Jeter’s first official hit in the Yankees’ employ was a bloop over the first baseman’s head in the first game of a double-header. “Everyone was laughing with me,” he said, “and that was a big load off my shoulders.”

  Derek went ahead and ripped off two singles in the second game, but his was a temporary refuge. When he showed up for work at the four-field minor league complex, Jeter never let on that he had been crying through the night in his room at Steinbrenner’s hotel. His coaches and teammates did not realize it, and the banned Boss—forever lurking in the shadows—sure did not realize it.

  “I had no idea he was that concerned about his ability to play professional baseball,” said his manager, Gary Denbo.

  How would he know? Every morning when Denbo arrived at the team’s Hines Avenue complex, next door to the home of the Tampa Bay Buccaneers, Jeter and another eighteen-year-old prospect, Ricky Ledee, picked in the sixteenth round of the 1990 draft, were waiting for him in the picnic area, eager to be the first players in the batting cage.

  They would also do extra conditioning after games, when most players had already fled the heat for the comfort of their air-conditioned cars and rooms. And through it all, Jeter wore a mask of clear-eyed determination.

  He was hurting behind that mask. “It seemed nothing was bothering him, that he had a positive frame of mind,” Denbo said. “I wish I knew. I would’ve helped him.”

  Denbo helped him more than he understood. When some in the organization were questioning whether Jeter would ever be a high-impact hitter at the big league level, Denbo tempered his leg kick and reminded him that the first part of his swing had to be an inside-the-ball move.

  Derek quickly applied these lessons to the games, while most lower-level prospects needed two or three years before they could accomplish against live pitching what they were accomplishing in the cage.

  Denbo also noticed Jeter was tilting the barrel of the bat toward the catcher when he moved his hands into the hitting position, or loaded. This was a fault common in hitters with long swings, but Denbo let the fault stand. The Yankees did not believe in breaking down prospects with too many tweaks too soon; they adhered to a thirty-day moratorium on suggested changes to a player’s approach.

  “They don’t want to screw up the good things you did that got you here,” Jeter said.

  One last thing Denbo noticed about his shortstop: he was about the most polite and professional kid he had ever met.

  Every single time Derek walked out of the cage, he thanked his coach or coaches for the help. “In professional baseball,” Denbo said, “that just doesn’t happen.”

  Overnight success does not happen, either. And even though Jeter responded to Denbo’s teachings as few students did, he remained a prisoner of his own doubts and insecurities when holed up alone in his room.

  Mark Newman, the Yankees’ coordinator of instruction, did not know about the crying or the kid’s wrenching struggle to find himself. Newman knew Jeter to be quick with a playful smile that could light up a clubhouse.

  But one day he sat next to Jeter at his locker and asked how things were going. “You know, I don’t think I can do this,” Derek confessed. “I shouldn’t have done this. I should’ve gone to Michigan.”

  Gone to Michigan? Newman was shocked by what he was hearing.

  “Derek was about as distraught as it gets,” he said.

  The executive assured the shortstop that it was common to struggle, that nobody in the Yankees organization cared about his rookie ball batting average. Newman advised Jeter to carry himself the same way whether he was hitting .150 or .350, just so people knew his would be a consistent presence.

  “You’re not going to be a good player,” Newman said, pausing for effect as Jeter shot him a look bordering on quizzical and pained, a look suggesting this was no way to comfort a beaten athlete.

  “You’re going to be a great player.”

  Derek’s face widened into a smile. Newman had pushed the right human button, finding out what a legion of executives, coaches, teammates, and members of the news media would discover in the years to come.

  Derek Jeter loathed criticism and thrived on positive reinforcement.

  So nearly every time he saw Jeter, Newman would tell him, “Hey, you’re going to be special. Stay with it. That’s an outstanding swing.” Denbo used the same lines, and Jeter responded just as the Yanks hoped.

  By the end of his forty-fifth Gulf Coast League game, with a double-header left to play, Jeter had actually lifted his batting average near .200. Derek had his first small triumph within reach, and privately all Yankee coaches and executives desperately wanted the .500 high school hitter to grab it.

  “He had to get four hits the last day to get over .200,” Newman said.

  Derek Jeter got those four hits. And as soon as he did, Newman told Denbo to remove Jeter from the second game. “We wanted Derek to go home over .200,” the executive said.

  Only Derek and his final .202 batting average were not going home near the end of August 1992. The Yankees informed Jeter they were shipping him off to Greensboro, North Carolina, to finish out the South Atlantic League season, and it did not matter that the shortstop would finally escape the searing heat, play some night games, and perform before an actual crowd.

  Jeter was crushed. Just when he had earned himself a chance to exhale, the Yankees threw him back into the Class A fire and ordered him to join a team that included a pitcher named Andy Pettitte and a second baseman turned catcher named Jorge Posada.

  The Greensboro manager, Trey Hillman, picked up Jeter at the airport and was struck by the kid’s comp
osure. Hillman knew all about Derek’s struggles in the Gulf Coast League, and he personally chauffeured the new recruit to the ballpark because, the manager said, “I didn’t want him to be scared on his first day.”

  To Hillman, Jeter did not appear scared at all. The Yankees wanted Derek to play some baseball under the lights and to get acclimated to the team he was scheduled to join in 1993, and Derek projected an aura of confidence and calm.

  But in Jeter’s first game, Pettitte was slapping a punctuation mark on what would be a 10-4 season, and he was in no mood for some malnourished shortstop to come in and foul it all up.

  On cue, Jeter started kicking around the ball on the left-hander’s watch. “Look at this guy,” Pettitte told himself. “Are you kidding me? This is our first-round draft pick?”

  Jeter felt Pettitte was showing him up with his body language, and he did not forget it. The shortstop hit a home run to compensate for his defensive blunders, and Pettitte did not forget that, either.

  Never mind that Jeter made 9 errors in 48 chances over eleven games. He hit a respectable .243 in Greensboro, and Posada said, “You saw what every Yankee saw, what every guy in the organization saw.”

  Poise. The same poise Jeter showed when he arrived at Yankee Stadium on September 11 as part of another trip Caruso had made a perk of the $800,000 deal. The agent wanted his client around the major league culture as much as possible, to make the ultimate goal feel only a few hard singles away.

  When Derek walked into the home clubhouse, some Yankee veterans jokingly asked him for a loan. A year earlier, one clubhouse attendant, John Blundell, saw Brien Taylor pass through the same door, “and he looked like he was on Mars,” Blundell said. “He was scared and didn’t know what to say. Taylor was in awe of the pinstripes and the big league locker room, even though we were awful.”

  Jeter wore a different look. At eighteen, Blundell said, “Jeter walked in there and you knew in his mind and heart he felt he was with his peers, and Brien Taylor didn’t have that presence at all.”

  Caruso, Jeter, and Jeter’s family ended up in Steinbrenner’s box near the dugout. The agent was sitting next to Derek, who had his legs and feet draped over a nearby seat, when a Stadium security guard asked Caruso in an annoyed tone, “Is he with you?” Derek straightened up, and soon enough a junior Yankee official came down to make sure everything was fine.

  “If you need anything,” Brian Cashman told Caruso and Jeter, “just let me know.”

  Derek did not need much that night or the following day, other than an update on the Michigan–Notre Dame game. He had enrolled for a semester in Ann Arbor and had attended his first classes the day before he arrived in the Bronx, where he spent part of Saturday, September 12, working out with the Yanks in full uniform.

  “Everything was larger than life,” Derek would say.

  He did not get to meet his all-time favorite Yankee, Dave Winfield, who was playing in Toronto, but Jeter did share the field with the likes of Don Mattingly and Wade Boggs, and he did take a tour of Monument Park. Cashman was responsible for escorting Derek and his family around the Stadium, and the junior official who was a year away from becoming the Yankees’ assistant general manager could not get over how much the supermodel-thin Jeter looked like the world’s tallest batboy.

  Derek had started a weight-training program at Michigan to supplement his summer workouts, and by year’s end he would add 16 pounds to his frame and push his weight close to 180. “But he was still so gangly,” Cashman said, “that you had to keep reminding yourself he was our first-round pick.”

  Cashman walked Derek and his family up the left-field side of the Stadium and escorted them into the Yankees’ own Hall of Fame beyond the outfield wall. As they moved from plaque to plaque, monument to monument, Cashman figured this was the right time to make the Yankees’ $800,000 bonus baby feel like a million bucks.

  He turned to Jeter and said, “Maybe you’ll have your number retired here one day.”

  Only Jeter was not worried about finding his way to Monument Park. He just wanted to get back to Michigan, back to the sanctuary of his dorm room, before the Yankees returned him to the school of hard knocks.

  The following spring in Fort Lauderdale, Whitey Ford was walking past the batting cage at the Yankees’ facility when a sight and a sound stopped him dead in his spring training tracks. Derek Jeter was taking his cuts on his first day of big league camp, and Ford decided to take in the show.

  Jeter delivered smash after smash after smash. “When I found out he was a shortstop,” Ford said, “I said, ‘Jesus Christ, I can’t believe it.’”

  No, Phil Rizzuto never swung the bat like this.

  Ford waited until Jeter was done, and then the Hall of Fame pitcher and the kid shortstop walked and talked until they reached the Yankee clubhouse. Ford complimented Jeter on his hitting, and he was taken by Derek’s apparent modesty and easy smile.

  “This kid’s going to be around for a long time,” Ford told himself.

  The Chairman of the Board was struck by Jeter’s arm and range at short, even if the infield instructor, Clete Boyer, would decree that Derek had “quite a ways to go.”

  Jeter was not going anywhere near the Bronx in 1993; he was in camp only to get a feel for how the Yanks went about their business. He hoped to make a strong second impression on team officials before heading back to Greensboro for a full season of Class A ball.

  If nothing else, Jeter made an impression on Don Mattingly, just as he had made one on Whitey Ford. The shortstop and the veteran first baseman were finishing up a workout on a back field, all alone, the seats empty, not a player or team official in sight.

  A spent Jeter had started walking off the field—no urgency or bounce to his step—when a jogging Mattingly came up behind him and in passing said, “Let’s run it in. You never know who’s watching.”

  Jeter caught up to Mattingly and the two raced to the clubhouse side by side. An elder’s wisdom had hit home. From then on Jeter would do everything—even head to the showers—at full speed.

  Team officials noticed. Jeter never expected to see the inside of a major league preseason game, never expected to hear the Yankees’ manager, Buck Showalter, turn his way and say, “Get ready.”

  “Ready?” Jeter thought. “Ready for what?”

  Ready to pinch-run for the New York Yankees, that’s what.

  Derek got his fifteen seconds of fame on the base paths, then was sent down to minor league camp with Brien Taylor on March 14, the same day the Yankees optioned a young pitcher named Mariano Rivera to the minors.

  Before he knew it, Jeter was packing his bags and hopping into a car with a teammate and fellow shortstop he had befriended, R. D. Long, for the 645-mile drive from Tampa to Greensboro to rejoin the Class A Hornets. Long was not anyone’s idea of a bonus baby; he was a college player at Arizona and Houston whom the Yankees picked in the thirty-eighth round of the ’92 draft.

  Five players were taken before Jeter in that draft, and 1,053 players were taken before Long. But as partners in middle infielder drills the eighteen-year-old phenom and the twenty-one-year-old long shot grew close and decided to be roommates.

  They jumped into the car when camp broke and made the ten-hour drive to Greensboro. “We listened to Mariah Carey the whole way,” Long said. “The kid had every single Mariah CD ever printed.”

  Mariah would be the background music for Jeter’s long and painful journey from bungling apprentice to master of his trade. In Greensboro, where the Hornets competed in the South Atlantic League, a low-level Class A consortium known as the Sally League, Jeter would play for a team that included other prospects with big league potential, including Mariano Rivera, Shane Spencer, Mike Buddie, Mike DeJean, Nick Delvecchio, Matt Luke, and Ryan Karp.

  The Yankee minor leaguers almost always knew how to carry themselves, and this group was no different. “We never had any problem with Yankee kids down here,” said the Hornets’ owner, John Horshok. “They were w
ell behaved, and they had so much information and training, they were almost afraid to screw up and not end up being Yankees.”

  Coming off elbow surgery in 1992, Rivera was most determined to get his burgeoning career back on track. He had been a weeping mess himself as a rookie in the Gulf Coast League three years earlier, when the language barrier left him yearning to return to his native Panama.

  But Rivera had adapted and grown up. One day in the Greensboro clubhouse he was barking at players, “Let’s go to work, let’s go to work,” when Long threw his cup of water at Rivera just for the hell of it.

  The water landed on a chart Rivera was holding, “and Mariano went ballistic and wanted to kill me,” said Long, whom the pitcher chased around the locker room.

  The Yankees were encouraged by Rivera’s competitiveness and had high hopes for a few Hornets, but Jeter was the jewel of the system, the one draft choice outside of Brien Taylor the franchise needed to develop. He would play in a lost-in-time kind of place, World War Memorial Stadium, a crumbling concrete structure near the North Carolina A&T campus.

  War Memorial opened in 1926—“You mean there was a World War I?” one Hornet asked a Yankee official—and welcomed Charles Lindbergh a year later. Among the nation’s oldest minor league parks, War Memorial was distinguished by the triple-arched main entrance, the perimeter resembling a backward J, the dim lights and choppy field, the wooden seats, the backed-up plumbing, the cramped clubhouses, and the pest-infested press box.

  “When you walked in there,” said Mitch Lukevics, the Yankees’ farm director, “you felt like you were going to see Roy Hobbs.”

  Only Derek Jeter was supposed to be the natural on this Greensboro team, the teenage prodigy among more experienced and less touted Hornets in their early twenties. He would play for Bill Evers, a former catcher from Long Island who grew up wanting to be the next Mickey Mantle, and for his trusted Gulf Coast League manager, Gary Denbo, who was Evers’s hitting coach.