The Captain: The Journey of Derek Jeter

by Ian O'Connor

  Jerry Manuel, who had managed the White Sox and Mets, said he would take Jeter over Rodriguez, Nomar Garciaparra, Miguel Tejada, Omar Vizquel, and every other modern-day shortstop in his prime. “No question I would start my club with Jeter over all of those guys,” Manuel said. “He gives so much to the game, and not to individual stats, that when the game’s on the line it gives back to him.”

  So legions of Yankees fans were proud that their sons and daughters chose to wear number 2, the most identifiable marker of an untarnished star. “If you wanted a son and didn’t have one,” said Leonard Biro, the father of Jeter’s lifelong friend Doug, “Derek would be the person to be your son. His character is very high. . . . He’s definitely a great example, unlike most of the others getting all that money.”

  Money. Derek Jeter was regarded as the ultimate money player, and yet one who never played for money.

  Only in the winter of his discontent, the winter after his 2010 season, Jeter was suddenly being defined in strictly financial terms.

  As in, How much should the Yankees pay an aging singles hitter who had a slugger’s impact on the franchise’s legacy and bottom line?

  Cashman, Levine, and Steinbrenner first met with Jeter and his longtime representative from Creative Artists Agency, Casey Close, on November 8 in Tampa. The meeting lasted several hours, and it opened with the Yankees assuring Jeter they wanted him to return, and with Jeter assuring the Yankees he wanted to play only for them. A good start.

  Steinbrenner did a lot of the early talking, telling Jeter how much he meant to his father, to his family, and to the franchise as a whole. Hal promised Jeter he planned on keeping him a Yankee for life.

  The captain responded by telling Steinbrenner he wanted the same thing. A better start.

  But then it was time to do business, a time that would end up fracturing the bond between iconic player and iconic team.

  “I just want what’s fair,” Jeter told the Yankees executives.

  Steinbrenner handed over the meeting to Cashman and Levine, a hardened money man who had been the chief labor negotiator for Major League Baseball and who had served as New York City’s labor commissioner and its Deputy Mayor for Economic Development, Planning and Administration under Rudy Giuliani.

  Levine had clashed with Joe Torre before Torre bolted for Los Angeles. He did not want to send Derek Jeter through the same door.

  Nor did Cashman, the former intern who rose through the organizational ranks by winning Boss Steinbrenner’s perilous game of Survivor. Cashman wanted Jeter back, too, but the general manager was a fierce competitor whose modest physical stature belied his appetite for the fight. Cashman was Willie Pep in a golf shirt and slacks.

  When the GM took over the meeting with a presentation on the state of Jeter’s game, he pulled no punches. In his gofer days, Cashman used to help Yankee Stadium security people pull unruly drunks out of the stands. As an executive he had gotten tough with the likes of Bernie Williams and Johnny Damon, and in his 2007 dinner with Jeter the GM proved he wasn’t afraid to get tough with the captain.

  So with Jeter sitting right there in this first round of contract talks, Cashman raised the concerns the organization had about the captain’s bat speed and range in the field, and his declining slugging and on-base percentages in two of the previous three seasons. It was a detailed and pointed critique, and Jeter did a slow burn while listening to it.

  The agent, Close, had his say in response, emphasizing his client’s tremendous impact on the franchise on the field and off, and the two sides parted without exchanging any hard numbers. If they didn’t agree on a contract in this first sit-down, they did agree to keep the negotiations private. The captain would have it no other way.

  Soon enough Jeter and the Yankees made their first informal offers. Close said his client was entitled to six years at $25 million a pop, and Cashman said he thought Close’s client was worth three years at $13 million a pop. These were parameters more than they were hard estimates, but still, the Yankees and their shortstop opened up the preliminary bidding three years and $111 million apart.

  Yes, Hal Steinbrenner had it right. Things could get messy.

  The Yankees increased their offer to three years and a $15 million wage, and Close countered with four or five years and a $23 million wage, which Cashman and Levine took to mean four years and a $23 million wage. The $111 million gap had been reduced to a $47 million gap.

  It was progress, painful progress, but the Yankees made it clear that Jeter would have to do almost all of the compromising from that point forward. Meanwhile, Jeter and Close were stewing over what they believed to be the team’s breach of their agreement to keep details of their talks out of the press.

  Following Steinbrenner’s radio remarks that the negotiations could get “messy” and that he needed to be mindful he was running a business, and Cashman’s remarks that he didn’t believe in paying players for milestones, Close told AOL FanHouse’s Ed Price that Jeter agreed “with Hal’s and Brian’s recent comments that this contract is about business and winning championships. Clearly, baseball is a business, and Derek’s impact on the sport’s most valuable franchise cannot be overstated. Moreover, no athlete embodies the spirit of a champion more than Derek Jeter.”

  The agent thought that would be the end of it, but his client was bothered by what he perceived to be additional organizational leaks in the news media designed to make him appear greedy, even delusional. Jeter wasn’t thrilled with Levine’s comments at the GM meetings, either, the ones making it clear that the Yankees were prepared to pay the shortstop only for his on-field skills.

  Jeter’s father, Charles, was as unhappy as his son over the team’s offer of a pay cut (the shortstop made $21 million in the final year of his $189 million deal), and over the way the captain was being portrayed in many corners of the media. That left Close in a difficult spot.

  The Yankees were willing to keep Jeter the game’s highest-paid middle infielder, they knew no competing team would offer Jeter a $15 million salary, and they knew Jeter wasn’t leaving for a competing team anyway. The agent had no market for his client’s services, no leverage, and no way to cloak the fact that Jeter was coming off his worst season.

  Close kept coming back to everything the captain meant to the brand, the ballpark, and the network. The agent did raise Alex Rodriguez’s monstrous $305 million contract (including up to $30 million in bonus money if he ultimately breaks the career home-run record) early in the negotiations, but A-Rod’s deal wasn’t something Close kept harping on.

  The agent did remind the Yankees that they had given a ton of money to players who hadn’t done a fraction of what Jeter had done for the franchise. None of it moved Cashman and Levine off their numbers.

  They argued that Close used A-Rod’s $252 million deal with Texas to land Jeter’s $189 million, when both were shortstops, and that the Yankees had every right to use comparable players in negotiations this time around.

  Levine and Cashman cited twenty-six-year-old Florida shortstop Hanley Ramirez, who had superior numbers to Jeter’s and was making $11 million, or $4 million less than the Yankees were offering. They cited the Dodgers’ Rafael Furcal ($12 million) and the Phillies’ Jimmy Rollins ($8.5 million), among others.

  Through grapevine intelligence, Levine was aware that Colorado was about to give twenty-six-year-old shortstop Troy Tulowitzki a seven-year extension that would leave him with $157.75 million over ten seasons, or an average of $15.775 million per. Despite the fact that Tulowitzki’s stats blew away his idol’s, the Yankees were quietly prepared to improve their offer to Jeter so that his average annual take would exceed the Colorado star’s.

  But the captain pushed for a salary of more than $20 million, and Close was being asked to pull a rabbit out of a hat that didn’t exist. If the agent had always beaten the Yankees at the negotiating table, this time he was destined to lose.

  With frustrations mounting inside the Jeter family and camp, with his cl
ient smoldering over a perceived campaign to make him look bad in the news media, Close decided to alter the game plan. He decided to go public despite warnings from Yankee officials that such a move could escalate hostilities and prove damaging to Jeter’s image.

  So when Close told Daily News columnist Mike Lupica that the Yankees’ negotiating stance was “baffling,” that they “continue to argue their points in the press and refuse to acknowledge Derek’s total contribution to their franchise,” and that there was a reason “the Yankees themselves have stated Derek Jeter is their modern-day Babe Ruth,” Cashman, Levine, and Steinbrenner lost it.

  Steinbrenner was the one who would decide the appropriate Yankee response. After concluding that Close had hurt the family business with his words, the Boss’s son ordered the Code Red and asked Cashman to carry it out.

  With his phone as his only weapon, the general manager launched a media offensive with something of shock-and-awe tone. Cashman’s money quote on Jeter was landed by ESPNNewYork.com’s Wallace Matthews, and it went like this:

  “We’ve encouraged him to test the market and see if there’s something he would prefer other than this. If he can, fine. That’s the way it works.”

  Meanwhile, Hal Steinbrenner’s brother, Hank, weighed in by telling the Associated Press, “As much as we want to keep everybody, we’ve already made these guys very, very rich, and I don’t feel we owe anybody anything monetarily. Some of these players are wealthier than their bosses.”

  Jeter was hotter than he’d ever been, hotter than he was over A-Rod’s remarks ten years back. The captain was particularly upset at Cashman’s dare to go test the market.

  Suddenly Jeter was caught up in a tabloid feeding frenzy, the very thing he’d worked so hard to avoid his entire career. And from a safe distance, while he was sunning himself on a yacht by Cameron Diaz’s side, A-Rod was loving every minute of it. Rodriguez was signed through his forty-second birthday, and he’d make a whole lot more than $15 million a year. The A-Rod–Jeter relationship was in a much better place, but the third baseman didn’t mind finally seeing the shortstop caught up in an A-Rodian drama of his own.

  In almost all of his interviews, Cashman pointed out that he still wanted to sign Jeter, and that he still believed Jeter represented the team’s best option at shortstop. But the GM would also point out, “There are things we have concerns with—his performance over the last few years, and his age. And that has to be factored into the negotiation.”

  Jeter accepted Cashman’s criticism in 2007. He wasn’t accepting this.

  The two sides had grown into enemy forces. Jeter and Close were looking at the Yankees the way the Red Sox were looking at them, and for a day or two the unthinkable was thinkable: maybe Jeter wouldn’t finish his career in the Bronx after all.

  With Cashman assuming the role of bad cop, especially in Jeter’s eyes, Levine came up with a proposal that the GM and Hal Steinbrenner liked. Over the long Thanksgiving weekend, Levine pieced together an elaborate incentives plan that would allow Jeter to make additional millions in a fourth year of the contract if he played at a high level.

  Levine was reviewing the details of his plan when Close reached out to Steinbrenner to arrange a second face-to-face meeting in Tampa. Understanding that the Yankees weren’t going to be giving his client another megadeal, a truth he had to explain to the Jeters, Close was hoping to bridge the turbulent waters separating the two sides and get the best deal he could.

  On November 30, Jeter, Close, and Creative Artists Agency attorney Terry Prince met with Cashman, Levine, and Steinbrenner. This summit lasted more than four hours, but Jeter was there for only the first forty-five minutes.

  The captain’s world had been turned upside down. His girlfriend, Kelly, had been named Esquire’s Sexiest Woman Alive (yes, Esquire owed Jeter one), and he had built himself a 31,000-square-foot waterfront mansion on Davis Islands in Tampa, where Jeter would have to make do with seven bedrooms and nine bathrooms.

  Only his life didn’t feel like an Everyman’s fantasy at the start of this second meeting. Jeter opened by telling the Yankee delegation how upset he was that they made the negotiations public, and by telling Cashman how upset he was that the GM dared him to shop for a better offer.

  When Jeter was done spewing, he tried to get up and leave before Cashman asked him to sit back down. The GM reminded Jeter that the Yankees’ offer was the highest offer. “You said all you wanted was what was fair,” Cashman told him. “How much higher do we have to be than the highest offer for it to be fair?”

  Cashman also blamed Close for making the contract talks public, a position Jeter and his agent rejected. They went back and forth for a bit before Jeter decided that his presence might hinder the process. As the captain excused himself, he made it clear Close was now authorized to make a deal.

  The sides made significant progress over the balance of the summit, and the agent and Levine then spent a couple of days on the phone tweaking the proposal. Knowing it would be a wise idea to keep his client and Cashman apart, Close asked Levine to go see Jeter in his Manhattan apartment on the afternoon of December 3.

  They met in the skyscraping Trump World Tower home Jeter had put on the market for $20 million, this while Cashman met with his other future Hall of Famer, Mariano Rivera, to work on the closer’s free agent deal in Rivera’s suburban Westchester home.

  The Rivera talks were as quiet as Rivera himself, even as the Red Sox were making an attempt to extricate him from the Bronx. Jeter was the one who had to scratch and claw for his money while millions of fascinated fans looked on.

  Inside his Trump home, Jeter told Levine he wanted more money added to the incentives clauses in the proposal. At the time the offer included bonuses for winning awards such as league MVP, World Series or League Championship Series MVP, Silver Slugger, and Gold Glove.

  Jeter spent a couple of hours arguing that those awards are very difficult to win, and that the contract numbers didn’t reflect the degree of difficulty. He made persuasive arguments. Levine absorbed the captain’s points, called Cashman and Steinbrenner while Jeter called Close, and the two sides ended up a yard or two away from pay dirt.

  As it turned out, Jeter made himself about $4 to $5 million in extra money in that meeting with Levine. The Yankees agreed to raise the ceiling on the incentives plan to $9 million, and that night the parties set up a meeting for late the following afternoon to close the deal at the Regency in the city.

  The same men who attended the second meeting in Tampa ended up in a Regency suite on Saturday, December 4: Jeter, Close, and Prince on one side; Cashman, Levine, and Steinbrenner on the other. They reached an agreement around 4:00 p.m. Everyone shook hands, hugged, and shared a laugh.

  Derek Sanderson Jeter was still a Yankee.

  Levine got fellow executives Lonn Trost and Jean Afterman on the phone to help dot the i’s and cross the t’s with Prince. The contract guaranteed Jeter $56 million over four years, with a player option after year three.

  The captain would make $48 million in salary in the first three years and would receive another $3 million if he decided to buy his way out of the deal and into free agency, leaving him with $51 million and an average annual take of $17 million, better than Tulowitzki’s $15.775.

  Jeter would have the option to stay for the fourth and final season for an $8 million salary plus potential bonus money earned over the life of the contract that topped out at $9 million, making it possible for him to earn as much as $65 million in the deal.

  Jeter would earn $4 million for winning a league MVP award and $2 million for finishing second through sixth in the voting. He could score an additional $1.5 million for a Silver Slugger, $500,000 for a Gold Glove, and $500,000 each for a League Championship Series MVP and a World Series MVP. Jeter would be eligible for any unearned bonuses during the fourth and final year of the contract.

  In order to save the Yankees on luxury tax payments applied to their massive payroll, Levine persuaded Jet
er to defer $7 million of his salary over the first three years, without interest, something the captain didn’t want to do.

  “I’m rooting for Derek Jeter; we all are,” Levine would say. “I hope he hits all of his incentives so we end up paying him $17 million in that fourth year. It will be the happiest $17 million we’ve ever spent.”

  Before leaving the Regency, Jeter met separately with Cashman and Steinbrenner to begin repairing the relationship. They had a long and winding road ahead of them.

  Some in baseball believed the Yankees were guilty of unnecessary roughness in their talks with Jeter. But just as many others, including some teammates of Jeter’s, thought the team had offered the captain more than it needed to.

  The deal was set to be announced on Tuesday, December 7, at George M. Steinbrenner Field in Tampa. At last, Jeter would get that big press conference denied him in 2001. At last, he would get his day inside the tent.

  The captain arrived in a blue pinstriped suit, and before he spoke, Cashman offered him a piece of advice.

  “Tell the truth,” the GM told Jeter. “Let’s not have a fake press conference. Let them see how pissed off you are at me, let them know that. I’m a big boy. I can handle it.”

  Shockingly, Jeter took Cashman’s advice. He stepped to the microphone, joked that he’d never had one of these press conferences before, and, with the YES Network cameras rolling, admitted he was pissed off by the way the negotiations went down.

  “I’d be lying to you if I said I wasn’t angry at how some of this went,” Jeter said.

  Angry. Nobody could recall Jeter using that word to describe his emotions about anything. Ever.

  Jeter revealed his rage over Cashman’s statement that he should go searching for a better offer from another team.