The Captain: The Journey of Derek Jeter

by Ian O'Connor

  Hayes had handed Jeter a Reds cap when he joined Bennett and Mock on a predraft visit to the Jeter home, and Hayes and Bennett left believing that Derek would be wearing that cap across his big league career.

  “We were sure we were going to get him,” Bennett said. “It was a done deal. He had blazing speed, he was smart, he hit rockets into the Riverfront seats when we had him in as a high school junior. Every single thing Jeter did was special.”

  With his team holding the first pick, a pick no team could sabotage, Newhouser did not mind sharing one little secret with Bennett. “No kid is worth a million dollars,” the Houston scout told the Cincinnati scout. “But if one kid is, it’s Derek Jeter.”

  Bennett did not need convincing, as he saw Jeter as Larkin’s equal. To those who were concerned about drafting a shortstop when the Reds already had a young All-Star there, Bennett argued that Jeter could play center field and then move to short when Larkin broke down.

  Mock wasn’t so sure. Without Larkin, he told himself, Jeter would have been the guy hands down. But Larkin was there, and Mottola had already given a verbal to a price out of a small-market team’s dream, $400,000, a steal at number 5.

  Mock had seen Jeter once, and Bennett had pleaded with him to go back a second time and see the shortstop on a healthier ankle. The scouting director never returned to Kalamazoo, other than to meet with Jeter’s parents.

  So as Mock gathered with nine or ten other Reds officials in a conference room, gathered around a speakerphone that symbolized the outdated way baseball’s elders conducted the draft (they practically used carrier pigeons to report the results), the guardians of his favorite boyhood team were holding their breath.

  In Tampa, Yankees executives were huddled around their own speakerphone inside the Harbor View Room at George Steinbrenner’s Radisson Bay Harbor Hotel. Those executives were feeling good after Bill Livesey, scouting director, made a morning phone call to his peer in Houston, Dan O’Brien, to ask what the Astros were planning to do at number 1.

  O’Brien and Livesey shared a mutual respect, so the Houston scouting director told Livesey the truth: he was taking Phil Nevin. Livesey confessed he was hoping Jeter fell to number 6, and before their brief exchange ended, they both agreed the shortstop would develop into an outstanding pro.

  Suddenly the outstanding pro-to-be was one pick away, and a wave of great anticipation roared through the Yankee room like a freight train in the night.

  As soon as the Orioles made Hammonds official, a voice from the commissioner’s office announced on the speakerphone that the Cincinnati Reds would select next. The Yankees had some twenty officials in their draft room, including regional scouting supervisors, a national cross-checker, Livesey, and Brian Sabean, the vice president for player development and scouting.

  Days of mass coffee consumption and passionate debates had taken their toll. Nerves were frayed as the Yankees waited for the sound of Julian Mock’s voice. Club officials were staring blankly at the boards in the front of the room that ranked the prospects by position, from top to bottom.

  “We beat up those boards for three or four days,” Livesey said. They kept changing the rankings, erasing names, restoring names, leaving at night, and then returning the next morning to do it all over again.

  On draft day, Jeter’s name was atop the list of shortstops, and everyone in the room agreed the Yankees should have and would have taken him had they owned the number-one pick. Livesey ran the strong preference for Jeter by Steinbrenner, which was an odd turn of events.

  Commissioner Fay Vincent had banned Steinbrenner for life from the day-to-day operations of the club for paying a gambler, Howie Spira, $40,000 to dig up dirt on Dave Winfield, who happened to be Jeter’s idol. Yet everyone knew the Boss was in full control of a shadow government.

  “It’s not like George disappeared by any means,” said David Sussman, the Yankees’ general counsel and chief operating officer. Steinbrenner readily offered his opinions on significant player transactions at quarterly partnership meetings (Vincent had allowed this). “George made it known in those meetings that he still owned the team,” Sussman said.

  Steinbrenner also made it known he was not especially fond of paying superstar wages to kids who had not proved a thing. The Boss came down hard on subordinates over the decision to pay Brien Taylor his record-shattering bonus.

  But when Livesey ran Jeter up Steinbrenner’s flagpole, assuring his employer the shortstop would be in the majors within four years, the Boss approved.

  The Reds were about to make their move, and the Yankees’ hour of reckoning had arrived. “It was a beehive of activity,” Livesey said. “We had a lot of manpower in the room. People on our files, people working the boards, people erasing names, people making calls.”

  The Yankees had not been to the playoffs since 1981, and they were in dire need of a break neither Jeter nor his adviser thought they were going to get. Jeter was so sure he was going in the top five, so sure the Reds would take him if the Astros did not, so sure he had no chance of playing for his boyhood team, “I didn’t even know the Yankees picked sixth,” he said. “I thought I was going to Cincinnati and that I’d be stuck behind Larkin.”

  Wearing a University of Michigan shirt, Jeter paced about his home as he waited with his family for the call. Out in Sacramento, Caruso gathered with a few aides in his office and stared at the phone. “We were preparing to negotiate a contract with the Reds,” he said.

  Paul Morgan, the Kalamazoo Gazette sportswriter who had covered Derek’s high school career, was feverishly working his desktop at the newspaper’s offices, hitting his refresh button over and over to get the latest Associated Press bulletins on a draft that was not televised.

  Morgan called the Jeters after a couple of picks were made, and when the phone rang Derek jumped out of his chair. With four selections in the books and the Reds ready to go, the sportswriter called back and told the shortstop he would contact him the second the AP posted his name.

  Jeter was overwhelmed by the very real possibility he would be selected at number 5. The franchises picking ahead of the Yankees knew of Jeter’s pinstriped preferences, yet that did not shape their decisions. Like the teams that went before them, the Reds merely wanted the best available player at the best possible price.

  Finally Julian Mock acted on his mid-jog epiphany. He leaned into the speakerphone and announced the Cincinnati Reds were using the fifth overall choice to take Chad Mottola of the University of Central Florida.

  A cheer immediately went up in the Yankee draft room in Tampa, one loud enough to echo across the Bronx. Fists were pumped and backs were slapped. Somehow, some way, Derek Jeter had made it unscathed to the sixth pick.

  Morgan called Derek with the news that the Reds had gone for Mottola, and that the Yankees were on deck. “Oh, God,” the kid said. A series of fateful choices—gross miscalculations, some observers believed—left the teenage Jeter holding a winning lottery ticket.

  Livesey wasted little time after the voice from the commissioner’s office announced the Yankees were up next. The scouting director turned to Kevin Elfering, the assistant scouting coordinator and director of minor league operations, who was reviewing the large computer printout of prospects’ names before him.

  “Jeter,” Livesey said.

  Derek Sanderson Jeter.

  Elfering found his name on the printout and noted his draft identification number—19921292. Elfering did not have a single thing to do with the scouting of Jeter, but he had the honor of making it official. “All I did,” Elfering said, “was say his name into the phone, Derek Jeter of Kalamazoo Central, and then he was ours.”

  Just as the commissioner’s office was repeating what Elfering had said, Reds scout Gene Bennett walked into the room where Mock and other officials were gathered. Bennett could not believe his ears.

  He heard a voice on the speakerphone say the Yankees had just taken Jeter, compelling the scout to blurt out, “Yeah, and the Cinc
innati Reds take Babe Ruth.” Bennett figured someone was pulling his leg, at least until a coworker told him, “Be quiet, we’re on the hookup.”

  A sick feeling came over him. Suddenly Bennett realized Mock had actually taken Mottola instead of Jeter, “and I couldn’t believe it,” he said. “Without question it was the most disappointing thing that ever happened to me as a scout.”

  A prototypical five-tool guy with size, Mottola was thrilled to be a first-round pick, never mind a top-five pick. He took the $400,000 deal with the Reds because he wanted to play baseball, because it sure seemed like a lot of money, and because nobody had projected him as a high draft choice entering his final year of college ball.

  But the fourth pick, Hammonds of the Orioles, would sign for $975,000. Even the twenty-fifth selection in that draft, Todd Steverson, scored a bigger bonus than Mottola did—$450,000 from Toronto.

  “A big reason the Reds took me was my signability,” Mottola would say. “When you’re that young you think, ‘Four hundred thousand to go in the first round? Great, where do I sign?’ You don’t realize people are trying to take advantage of you.”

  The Reds scout who saw Jeter the most, Fred Hayes, was just as devastated as Bennett. Jim Bowden, Cincinnati’s thirty-one-year-old director of player development and a man on the verge of becoming the youngest general manager in baseball history, could not believe Mock had ignored Bennett’s claim that Jeter could develop into a better player than the O’Neills, Sabos, and Larkins he had signed in the past.

  Mock was not moved by anyone’s counterarguments. He explained he did not know if Jeter would ever play shortstop for the Reds and figured Jeter might end up getting traded to another club.

  “I thought of our needs,” Mock said, “and of the fact I thought we had a superstar in Mottola.”

  Before he could do any of that explaining, Morgan was on the phone and speed-dialing the Jeters. The sportswriter knew if he did not get to Derek immediately after the Yankees selected him at number 6, he would never get through.

  Morgan even beat the team and Dick Groch to the punch. This time Charles Jeter answered the phone.

  “Charles, has he heard yet?” Morgan asked.

  “No,” the father answered.

  “He’s a Yankee.”

  Charles let out a cry of unmitigated joy and immediately handed the phone to his son.

  “Derek, you’re going to be a Yankee,” Morgan told him.

  “I can’t believe it,” Derek shouted. “I just can’t believe it.”

  Morgan heard bedlam breaking out in the background, and the sportswriter let Derek go, knowing the Yankees would be trying to call. Morgan hopped into his car and headed to the Jeter home.

  Meanwhile, Sharlee Jeter wrapped her big brother in a hug before her father shook Derek’s hand.

  “I’m so proud of you,” Charles shrieked. “New York Yankees. That’s your dream, man!”

  It was as if Jeter had willed this to happen. All those years of wearing Yankee shirts and caps and pendants, all those promises to friends, teammates, and teachers that he would grow up to become the shortstop for the world’s most famous ball team—they created some cosmic force too potent for an antiquated draft system to repel.

  The dreamer was living the impossible dream, yet one that still required a signature and the rejection of a free education at Michigan.

  The Yankees’ Brian Sabean immediately began negotiations with Caruso, a labor relations consultant turned beginner agent who landed Jeter as a client after landing A. J. Hinch, the Oklahoma high school star.

  Caruso would come to see Jeter as the second-best teenage prospect he had ever seen, right behind a Miami phenom named Alex Rodriguez. On a strong recommendation from Hinch’s father, Charles Jeter had invited Caruso to Kalamazoo and, over a few slices of pizza, agreed to let him represent his son.

  “Then [Scott] Boras showed up at the airport and he was bugging Charles a couple of weeks later,” Caruso said. “Charles, to his credit, wouldn’t let Boras come over because he’d already made a deal with me.”

  Caruso would go to bat for Jeter, a client he saw as “a skinny seventeen-year-old who barely said three words,” a client who lived in a home modest enough to greet a visitor with a broken handle on the screen door. That modest existence was about to change in a big six-figure way.

  Sabean faxed Caruso an opening offer of $550,000. The agent assured the Yankee executive these negotiations would not be nearly as acrimonious as the Brien Taylor talks but also told him that bid would not get it done.

  Caruso wanted to beat the $725,000 bonus Toronto had given the California high school star Shawn Green and his agent, Moorad, the year before. As the faxes and phone calls went back and forth, Jeter phoned the Michigan head coach, Bill Freehan, to seek his counsel. Freehan was in a delicate spot—he wanted Jeter on scholarship in the worst way, but as a former All-Star catcher with the Tigers he understood the lure of the big leagues.

  “The kid wanted to go to Michigan,” said Freehan’s assistant, Ace Adams. “No one knows this, but Jeter did not want to sign [with the Yankees]. He wanted to go to Michigan with his girlfriend, and he wanted to play there.”

  But the Yankees kept inflating their offer. Derek called the Michigan head coach and said, “Mr. Freehan, what should I do?”

  “You’ve got to sign,” Freehan finally told him. “You’re crazy if you don’t.”

  Adams was flabbergasted over his boss’s show of integrity and good faith. “I don’t think many college coaches would’ve ever said that,” Adams said, “but Bill was such a classy guy.”

  Jeter listened to Freehan. On June 28, 1992, two days after his eighteenth birthday, Jeter signed an $800,000 deal with the Yankees that included a $700,000 bonus (Caruso’s 5 percent cut amounted to $35,000) and enough to cover the full ride to Michigan that Jeter was giving up. His deal at number 6 doubled Mottola’s at number 5 and beat those signed by the top three picks.

  Freehan reached out to Adams, who was driving on the New York Thruway and returning from the Cape Cod League when his boss broke the news.

  “Derek just signed with the Yankees,” Freehan said.

  “Oh, shit,” replied Adams, whose long journey home had just gotten three times longer.

  Derek Jeter, who graduated twenty-first in a Kalamazoo Central class of 265, would not be continuing his education at Michigan. Instead, Charles Jeter would take his son to the airport for a flight to Tampa and a spot on the Yankees’ rookie team in the Gulf Coast League.

  When Charles took his last look at Derek before he boarded that plane, the father thought the son looked a lot younger than eighteen. After he returned to his car to begin the drive back to his Battle Creek office, Charles began to weep uncontrollably.

  “As soon as the plane took off,” Derek would say, “I realized there was no turning back.”

  His touchdown in Tampa marked the end of innocence. Derek was not an amateur prospect hobbling around in high-top cleats anymore. He was a corporate asset, a commodity, a highly compensated employee.

  Charles did not know if his child was up to handling the transition. And in the first weeks of what was supposed to be a dreamy Yankee life, it became clear Derek Jeter was a boy ill prepared to become a man.

  3. E-6

  The first high school player selected in the 1992 major league draft had a problem, and a big one:

  He wanted to go home to his mother.

  Derek Jeter could not hit a professional curve ball or fastball and could not get past the sinking feeling that all his fellow rookies and coaches in Tampa were asking themselves this one question:

  How the hell did the New York Yankees make him their number-one pick?

  “It was the lowest level of baseball,” Jeter said, “and I was awful.”

  Alone in a faraway hotel room in the summer of ’92, a child overwhelmed by grown-up stakes, Jeter could not get a grip on his runaway emotions. So he would call his parents, his sister, his girlfriend,
and tell them that he had made a terrible mistake, that he should have taken the four-year scholarship to Michigan.

  Sometimes the calls came at 2:00 a.m., long after Charles and Dot and Sharlee had gone to bed. The minute the phone rang they knew Derek had suffered through another dreadful day at the plate, and that he was busy trying to cry himself to sleep.

  Night after night after night, Jeter sobbed for relief that would not come. “That was a nightmare,” his father said.

  Derek had been a sorry sight on arrival in Tampa, a scarecrow come to life. His ankles were so skinny, his high-tops flapped about even when they were laced as tight as could be.

  Jeter would not be allowed to wear high-top cleats in games or practices (Yankee policy prohibited them), another reason he was not comfortable. Derek had never been away from home, outside of his summertime trips to his grandparents’ place in New Jersey.

  He was not in Tampa to play catch with Grandma Dot. He was not spending any long afternoons at the Tiedemann castle and splish-splashing around Greenwood Lake on the Yankees’ dime.

  The team was laying out $800,000, and the shortstop who was just days removed from his eighteenth birthday was supposed to honor the investment.

  “We’re expecting big things from you,” George Steinbrenner told him the day they first met.

  “And Derek was scared to death,” said his agent, Steve Caruso.

  Derek had his reasons. Finally done with his bonus negotiations, Jeter showed up late to the Class A rookie ball season and late to his first double-header.

  “Everyone was looking at me,” Derek would say. “I’m the number-one pick.”

  Jeter had felt the same stares bearing down on him while he ate in the dining room at Steinbrenner’s Radisson Bay Harbor Hotel, and they unnerved him. No, he was not even remotely ready to play up to the numbers in his contract.

  The same Jeter who struck out once in twenty-three games during his senior season at Kalamazoo Central struck out five times and went 0 for 7 in his first double-header as a pro in Sarasota. Derek faced a knuckleballer in the first game; he had never faced a knuckleballer. Derek faced a pitcher throwing 90 miles per hour in the second game; he had never faced a pitcher who threw so hard.