by Bob Klapisch
For eight years, Cashman has staged a counterintuitive ritual. Each December, the normally cautious GM rappels down the face of a steel-and-glass tower to help launch Christmas season in Stamford, Connecticut. Dressed in a preposterous elf hat and gloves, he’d just descended the Landmark Building when he heard that Shohei Ohtani—a pitching/slugging phenomenon who was the purported Babe Ruth of Japan—had crossed the Yankees off the list of teams he would sign to play for this season. “He was our target, like every team in baseball: big arm and could really swing the bat,” says Cashman. (With a pedigree for luring Japanese stars—Hideki Matsui and Masahiro Tanaka, just for starters—the Yankees had been clear favorites to get Ohtani.) Though he was under no pressure to devise a plan B, Cashman harked back to his chat about Stanton at the GM meetings. “I’d left the conversation with Hill at, ‘Hey, I like your asset—this could play in the event we don’t land Ohtani.’”
Till then, he’d really spent no time conceiving a Judge-and-Stanton lineup. Cashman is a grinder who prefers the hedged gamble to the high-risk, high-reward plunge. His best trades have always been for players on the come, or for someone’s distressed asset at cost—a Didi Gregorius before he hit left-handers, a David Justice instead of Sammy Sosa. But in the weeks since he’d spoken to Hill in Orlando, the Marlins, meaning Jeter, had mucked things up. Word leaked out that their ultimatum with Stanton had failed, leaving them stuck with the slugger and his monstrous contract. Worse, none of the teams on Stanton’s wish list would bite, even at a heady discount. The Marlins were going to have to pay someone to take their franchise star—to actually attach a fat check to offset his salary.
Cashman tasked his war team—Tim Naehring, vice president of baseball operations; Mike Fishman, the assistant general manager and director of the Analytics Department; and Afterman, the vice president in charge of contracts—to run the cost-benefit splits. Then he texted Hill, knowing not to call Jeter. “He wasn’t interested in speaking, which, you know, whatever,” says Cashman. At some point, Jeter realized that he’d nowhere else to turn and delegated the job to Hill. “Which is fine,” says Cashman. “I like Michael a lot. He’s a guy I’ve done deals with before.”
That week, the one leading up to the 2017 Winter Meetings, Hill and Cashman volleyed texts, knocking names and numbers back and forth. (Almost no one actually speaks now when making a trade. Cashman, a stickler for returning calls—it’s one of the traits that endears him to his peers—says type is better than talk as deals evolve. There’s no heat-of-battle tension in five-word squibs.) Hill started out by asking for the moon. He wanted a haul that began with Gleyber Torres, the Yanks’ best prospect, and also included their Single-A phenom Estevan Florial. Cashman countered with third-tier kids and insisted that Hill take a veteran back—he’d never get sign-off from owner Hal Steinbrenner if he didn’t move some money to offset Stanton’s. For forty-eight hours, his hopes rose and sank; at least twice, Cashman thought he’d missed his chance. The Marlins put out word that they had heat with other teams, though Cashman’s contacts at the MLB office told him it was just smoke, not fire.
On December 8, Cashman left the Stadium late, no surer of his footing than he’d been that morning. Earlier in the day, he thought he’d struck a deal, trading two young pitchers and the veteran Chase Headley for Stanton and $30 million in deferred cash. Things were far enough along that Cashman made two calls. One was to Hal Steinbrenner, the general partner of the Yankees and a man wired more like Cashman than his father. After years of acquiescing to the Big Stein template—wooing All-Star free agents and wildly overpaying them to placate fans and keep the Stadium full—Hal had come around to Cashman’s view that you couldn’t mortgage a championship anymore. It had worked for them once, in the winter of ’08, when Hal spent almost half a billion dollars to win the ’09 World Series and to baptize the new Yankee Stadium. But every max contract is a devil’s bargain: what you get from a star on the front side of his deal will cost you, in spades, later on. By 2012, the players he’d signed for vast sums—CC Sabathia, Mark Teixeira, and A. J. Burnett—were sucking air, and Burnett had tanked so badly that the Yankees paid the Pirates to take him off their hands.
Still, your dear-bought habit is harder to break than the one that costs you nothing. In 2014, Hal splurged again on a haul of top free agents. That group, anonymous and painfully dull, never made it as far as the Division Series. It was out of their failure that a new way was born, a thorough reinvention of team culture. Mark Newman, the farm director and a George Steinbrenner holdover, was not so gently prodded to retire. His successor, Gary Denbo, was empowered by Cashman to radically overhaul the minor league chain. Big sums were spent on sports science and analytics and the psychosocial training of young players. One example among many: the Yankees hired a corps of high school instructors to teach language and life skills to recruits. From the bottom of their development system—the baseball academies in Latin America—to the Instructional and lower-tier minor league clubs, the Yankees invested heavily in cognitive and social development to boost their signees’ chances to advance.
In countless ways that skirted the luxury tax, the team grew its operational base. “We were three people, total, in the New York office when I started in ’01,” says Afterman. “Now we’re well over fifty here, and it’s almost as many down in Tampa.” That bifurcation of power—the Yankees are the only franchise in major league baseball with executive branches in two cities—was implemented by George in the ’70s. Though he boasted the merits of internal “competition,” his real motive seems to have been paranoia. “He thought he was King George” and worried that his courtiers “would get him” if he didn’t spread them out, says a team insider. “He never really got that he actually owned the team and that no one could up and replace him.”
The George years and their Medicean backstage jousts will be unpacked at bloody length in a later chapter. But the story of this team, the one that emerged from the last big fail in 2014, begins with Brian Cashman mending the gap between the northern and southern offices of the Yanks. All baseball decisions now run through him, though the team’s three pillars—the heads of analytics, scouting, and business affairs—have a seat at his conference table. It isn’t till they’ve had their say and reached consensus that Cashman brings a potential deal to Hal. Hal then talks to his own consigliere—his older brother Hank. “Hal knows the business, but it’s Hank who knows baseball,” says a staffer of the brother who stepped back in 2009 to look after the family’s stables in Ocala. “He always kept a hand in after George died. Hal does nothing without going to him first.”
Sometime before midnight on December 8, the Marlins came back to Cashman about the deal: they’d do the Stanton trade for a better hitter than Headley. Cashman quickly subbed in Starlin Castro, a moody star with a line-drive swing whose successor was ready and waiting: Gleyber Torres. All that remained was to make a second call, this one to Cashman’s best player. “I phoned [Aaron] Judge to make sure I dotted every i,” he says. “If there was an issue, I needed to vet it with him, not have him hear about it later from the Post.”
It’s rare that a GM consults his star before pulling the trigger on a trade; it’s rarer still to consult a star who’d just finished his rookie season. But what a rookie season—and what a star. Judge was selfless and sweet-natured, a franchise talent with the character to match and shoulders that could carry a whole roster. His transformational power had goosed their stale lineup, made it feared and fun and must-watch TV, beginning with his batting-practice rockets. He carried that energy into the clubhouse, where the team adopted his spirit: free and easy, a group of kids thrown together, enjoying the ride of their lives. By the middle of May 2017, Judge was the face of the franchise; by July, he was the face of the sport. He was too nice a guy to be nettled by a trade, or too nice a guy to say so. But as Cashman had learned with the Jeter follies, a star’s pride must be honored. Offering him early buy-in, or the illusion of it, can save a team’s chemist
ry.
“Judge was like, ‘Wow! That’s incredible—what’re you waiting for?!’” says Cashman. “I said, ‘Well, it could affect your time in right.’ He said, ‘Whatever. I’ll DH or play left!’” Through a variety of scouts, Cashman had heard the same thing about Stanton: he’d do anything the Yankees asked of him. Some of those sources were Marlins people; they so badly wanted out that “I knew I could trust their information,” says Cashman. “It was, ‘Here’s what I got on Stanton . . . Now, can you hire me?!’”
Cashman sent the good news to Hal via text, knowing he’d gone to bed early. Then, having staged the heist of the year—adding the premium slugger in baseball to a monster lineup that had terrorized the league last season; clearing enough money to absorb Stanton’s deal and still get under the luxury tax threshold; and giving back nothing but a couple of kids who were years from the major leagues—Cashman drained his beer and went straight to bed, leaving the fantasy fallout to the press. “I don’t think like that,” he says of the carnage to be wreaked by Judge and Stanton. “My job is to get as much talent as I can so we take a shot at the title. If I do my job well, we’ll get multiple shots. The rest of it, the projections—who has time?”
Fifteen teams hold spring training in Florida; none of them host a venue as crass and sharp-elbowed as George M. Steinbrenner Field. You’d never mistake it for LECOM Park in Bradenton, an ancient facility where the Pirates play their games in front of a couple thousand seniors roused from naps, or Dunedin Stadium, the snowbird quarters for the Blue Jays that’s essentially a high school diamond. No, “The George,” as locals call it, is less a ballpark than a fortress, a monument to northern inhospitality on the fringes of sleepy Tampa. At the Stadium in the Bronx, you’re accosted on the concourse by anti-terror troopers toting rifles. Here, a bulwark of permanently parked squad cars is posted at the gate, and ex-cops and prison guards work security after taking early retirement in New York. To the pinstriped tourists with their Crocs and canes, limping past the guards at the metal detector, the message of this place is, We SEE ya, pal. Watch where you’re pointin’ that foam finger.
For ten years, Joe Girardi looked and acted like one of those uniforms patting people down. It wasn’t just the crew cut and bulging forearms, the severity of the pious Christian soldier. He managed games with such clenched-fist tightness, you feared he’d have a stroke making a mound trip. Even with four-run leads, he’d haunt the top step, the skin of his jaw stretched to its break point.
A bright, dexterous man who was rarely outmaneuvered and whose handling of his bullpen was superb, Girardi had the chops to become an institution, a skipper who stuck around for twenty years. But if he ever had a moment’s pleasure managing the Yanks, you wouldn’t have known it from his face. He was terse to the point of monkish with writers and came off badly on the postgame shows that he was contractually obliged to do. “We were shocked by that,” said a Yankees executive who’d pulled for his hiring in ’08. “He’d been great in the booth before taking over—sharp and relaxed, a good listen.” Then he came in and “pissed off the writers by being the guy who gave ’em nothing.” It was brutal to watch him in the media room, giving sour answers to softball questions while wearing a perma-frown. He never seemed to grasp that it was a privilege, even a thrill, to run the greatest franchise in American sports.
Each spring he would walk the clubhouse floor staring straight ahead, not so much as nodding at his players. As a manager explained to us several years back, there’s a formula for working the locker room. “You spend ninety seconds a day checking in with each guy—just enough to let them know you care,” he said. “Do less than that, they think you’re a prick; do more, they think they run the show.” Players, he went on, don’t want a friend. What they want, without knowing it, is a dad. A Yankees executive picks up the point, saying there are three kinds of leaders. “There’s the good dad, the stern dad, and the cool dad,” he says. “We’ve had all three of them in a row now.”
The good dad was Joe Torre, an avuncular skipper who steered with a light touch and a salty calm. With the exception of Joe Maddon, no manager in memory has had a feel for athletes’ psyches like Padre Joe. Like the priest his parents hoped he’d become, he made everyone in the room feel seen and heard, especially guys struggling at the plate. Tino Martinez, who replaced the sainted Don Mattingly when he arrived via trade in ’96, remembers getting off to a wretched start and being angrily booed that April. “Joe called me into his office one day—he’d made reservations at his favorite Italian restaurant for me. He said, ‘Take your wife out and enjoy yourself. And by the way, you’re my first baseman, end of story.’”
But the Torre who liked being loved by his players was reluctant to take them on. This was especially so with superstars: he refused to go after them when they dogged it in August or lost a step in the field. Near the end of Torre’s tenure (he managed from 1996 through 2007), Cashman asked him to talk to Jeter about relinquishing the shortstop job. “Derek’s defense was killing us, and I said to Joe, ‘I look at him like a Robin Yount. He’s awesome at fly balls, he’ll be a great center fielder.’ Joe said, ‘Fine. I’ll talk to him.’”
A couple of days later, Torre said that he’d spoken to Jeter and the shortstop had “no interest in doing that.” Displeased, Cashman made a note to himself: he’d take it up with Jeter face-to-face. A year later, he and Jeter were having dinner at a restaurant on the Upper East Side. “I told him the reason Torre talked to you about moving to center was because of how bad you were defensively.” Jeter was mortified: “‘What’re you talking about? You’re saying my defense is bad?’” Torre, Cashman learned, had never talked to Jeter, nor did he ask Larry Bowa, his infield coach, to have the talk with him. “Bowa would come to me like, ‘I’m working with him, Cash. We’re trying everything we can!’” But he’d never mentioned defense to Jeter either—not at least according to Jeter. “One thing with Derek: he doesn’t lie,” says Cashman, who filed the matter away as a leadership lesson. “Now,” he says, “I don’t just trust people to do the job they’re paid to do.”
Sometimes the good dad’s just the checked-out dad—the guy with his feet up on the coffee table while his teens stumble in at 3:00 a.m. For the last five seasons of his twelve-year stint, Torre let the clubhouse run itself. “He spent more time reading the Racing Form than going over scouting reports,” says a club insider. He’d garnered four rings in his first five years, won the Eastern Division title ten times out of twelve, and managed the Yanks into October every season. Even when he fell short, Torre got rewarded: the addition of Jason Giambi after losing the ’01 Series; the addition of Alex Rodríguez after dropping the ’03 Series. The late-’90s team of twenty-something kids who’d matured and caught magic together was now an Ocean’s Eleven cast of giant egos. The Gary Sheffields were rubbing shoulders with the Randy Johnsons and Mike Mussinas—twenty-five players, twenty-five publicists, as they say. Small wonder that, presiding over a squad of superheroes, Torre chose to rest on his laurels.
But it was the marketing of those laurels that undermined and eventually ruined his relationship with Steinbrenner. The breakup was years in the making, as the two had already begun drifting apart. Torre was 67, but popular enough to score one endorsement deal after another, as if he was still ten years younger and managing the golden-era teams of the late ’90s. Steinbrenner never bought into Torre’s celebrity, though: he seethed that these were his Yankees, not Joe’s, and didn’t appreciate being shoved off the stage. That, more than money or the championship drought, spelled the end of Torre’s run in the Bronx.
In Girardi, Cashman chose the anti-Torre: an avid overpreparer who’d speak the truth to his stars and take advantage of the data set before him. Both men believed in the virtues of structure: you put together a plan and a staff to carry it out, then communicate it constantly up the line. Cashman, who’d won concessions when he re-upped in 2005—the power to make decisions, to grow the New York office, and to bolster his m
ajor league scouting staff—had binders and spreadsheets on player matchups and now a manager eager to use them. Girardi showed up early to sit with his coaches, poring over heat maps and pitch progressions, the first wave of deep-dive analytics. What wasn’t in those folders was the softer stuff: intel on his players as human beings. “He didn’t listen to their music, didn’t watch the movies they watched—he had no interest in what interested them,” says an executive. Beginning in 2012, word came up from the clubhouse: the players didn’t like this guy. “Ten years ago, if they didn’t like the manager, they still busted their ass for him. Not anymore. These guys are millennials. Now it’s, who the fuck are you?”
By the end of ’17, it was clear Girardi was done: he hadn’t just lost the room, he’d lost his drive. In July and August, when the club stopped hitting, it seemed to team officials that he’d packed it in. He retreated to his office and wouldn’t come out, even to talk to his coaches. “It was like he wanted to be home with his kids,” says an executive. “I thought he was done with managing altogether.” And then, out of nowhere, the lineup caught fire and Girardi reengaged in September. He navigated the wild-card win over the Twins, the ALDS upset of the heavily favored Indians, and the thrilling comeback in the ALCS when, down 0–2, the Yankees swept at home and returned to Houston leading 3–2. They were brought up short by two brilliantly pitched games, but Girardi had the hunger again. His team had made the turn, gotten young and kinetic, and was positioned for a long, heady run. Yes, his deal had lapsed, but he had credit in the bank: the championship team of 2009 and ten winning seasons out of ten. Having frog-marched the club through its wilderness years—that post-’12 stretch when Jeter was in decline, A-Rod was in disgrace, and the Yankees’ farm teams sent no help till Sánchez arrived in ’16—he’d earned himself the right, he thought, to opt back in and reap the rewards of the next five years.
