CASH VS JETER
THE INTRIGUE & ANIMOSITY BETWEEN THE TWO REVEALED
From the new book “Inside the Empire: The True Power Behind the New York Yankees” (Houghton Mifflin Harcourt, out March 26).
THE GENERAL MANAGER Meetings each fall are baseball’s version of a buddies’ fishing junket to Belize. Executives harrowed by the grind of the season — six months of seven-day/ eighty-hour weeks; back-page eruptions after three-game slumps; and side-eyed shade from their high school daughters over another pre-prom party not attended — disappear for four days in mid-November to a luxe hotel overlooking a golf course. None of the GMs can putt worth a damn, but the greens are beside the point. Their fixed destination is the lobby bar, where someone’s playing piano, the shades are drawn against the late-fall sun, and thirty men with the hardest jobs in the trade can let loose and get buzzed. Not a lot gets done at these boys’-club excursions, in part because of the calendar. The free-agent market is barely a week old, no one’s finalized his forty-man roster, and the needs of each team won’t fully manifest until the frenzy of Winter Meetings one month hence. Those events, held in mid-December at another Kubla Khan luxe resort, are a Ford Bronco chase of trades and desperation, capitalism on a four-day crack toot. Still, it’s not like nothing happens at the GM meetings one month prior. Over third and fourth cocktails, GMs pull each other’s strings for leads on what they hope they’ll get done later. At one point or another, most will pay homage to the guy or two holding all the cards: the lucky executives who happen to have deep wells of talent on their Doubleand Triple-A rosters. In this, the Age of the Real-Deal Drug Test and the Can’t-Miss Hall of Famer Clogging the Lineup, nobody wants the fading superstar with the enormous contract. What the GMs want — overwhelmingly — is to get younger and cheaper: to trade a couple of peak seasons from their franchise left fielder for a pair of live-armed kids who are on the brink.
IT WAS precisely in that spirit of here-goes-nothing that Mike Hill, the director of baseball operations for the fire-sale Miami Marlins, tapped Brian Cashman on the shoulder in November 2017 in the hallway of the Waldorf Astoria in Orlando. After fifteen years of being a reluctant shopper — the one guy who showed up every winter with strict orders to overpay for back-nine players — Cashman, the general manager of the New York Yankees, was suddenly in the catbird seat. Through a series of canny drafts and quickstrike deals at the trading deadline a year or so back, he’d miraculously recast himself as a master builder, the cool kid with all the hot toys. He had seven of the hundred best prospects in the game (plus a wave of kids behind them who were almost as good) and a major league roster of newly minted mashers who’d bulled their way to within a game of the World Series.
Cashman also had the one great luxury in the room: permission to do absolutely nothing. His Baby Bombers had come of age two years early and bought him a full season to sit tight. With a mix of pending superstars on minimum-salary deals (Aaron Judge, Gary Sánchez, Luis Severino), cut-rate acquisitions on the cusp of stardom (Didi Gregorius, Chad Green, Sonny Gray), and just the right garnish of graybeard leaders to run the locker room (Brett Gardner, CC Sabathia, David Robertson), he could bide his time for the auction to end all auctions: the 2019 free-agent class. Come November of the following year, he’d have a hundred million or more in luxury cap space to add the keystone blocks for a five-year run: perhaps Bryce Harper to bang dents in the second-deck facade, Manny Machado to anchor a world-class infield, or Clayton Kershaw to start Game 1 of the World Series.
Still, you know: it never hurts to talk. “We were walking down the hall when either Hill or I broached the subject of Stanton,” Cashman says. Giancarlo Stanton was the circus-strongman slugger who’d pummeled the National League for eight years. Fresh off a fifty-nine-homerun season and a Most Valuable Player Award in 2017, he was a wild extravagance on the now-threadbare Marlins, a Ferrari at a drivein showing The Florida Project.
The Marlins franchise (and its many hundreds of millions in debt) had been sold months before, for $1.2 billion, to a baggy-suited rich guy by the name of Bruce Sherman and his new partner, Derek Jeter. Of the several entities that pursued the Marlins (among them, a consortium headed by Jeb Bush and another by Jared Kushner’s father, Charles), the Sherman-Jeter group seemed the least provisioned to ride out years of heavy losses. Sherman had walked away from Private Capital Management, his wealth management firm, after a string of big bets blew up in his face. Among them were sunk positions
in Bear Stearns, the Great Crash failure, and newspaper chains like Knight Ridder and Gannett that chunked off billions of dollars in high-speed losses. Over four years’ time, PCM’s portfolio shrank by 90 percent. To be sure, Sherman owned a $70 million yacht, which he had humbly christened The Majestic, and he’d deftly repotted himself in old-growth Naples, where he chaired a wine festival every winter. But in team-owner waters, he was plankton to sharks, a multimillionaire in a billionaire boys’ club.
The Sherman-Jeter purchase of the Marlins was predicated on a promise that they’d made to the other owners in the game: that they’d instantly strip the team of homegrown stars and slash its obligations to the bone. Having overshot the market by about $200 million — their chief rival, a construction magnate named Jorge Mas, had stopped bidding at $1 billion — they told their fellow owners that they’d go the Houston Astros route: tank for four years while turning a modest profit and building back a core of young talent.
But it’s hard to make a buck by wooing pissed-off fans, then playing them for suckers two months later. Pre-sale, Sherman and Jeter advertised a team built around assets like Stanton. After the deal closed, though, word leaked to the Miami Herald about a secret prospectus given to investors. It talked up scorched-earth payrolls, absurdly robust gate sales, and cash infusions from a phantom TV deal. This, after Jeter and Sherman botched the takeover by firing goodwill legends like Andre Dawson and Jeff Conine and dumping a longtime scout with colon cancer. As southern rollouts go, this was William Tecumseh Sherman burning down Atlanta. At a town hall meeting to assuage hurt feelings, Jeter kiddingly told a fan that he could throw out the first pitch, as long as he bought a ten-year ticket plan.
The first big name Jeter put on the block? Giancarlo Stanton. Stanton, among the highest-paid position players in baseball, had ten years left on a thirteen-year deal worth $325 million. Alas for Jeter, Stanton also had leverage — veto rights over any proposed trade. For eight years, he’d played the good-egg soldier, hacking ninety-loss seasons in 100-degree heat to stand sweat-soaked and disheartened in right field. As his agent, Joel Wolfe, told USA Today, “he spends Octobers in Europe, unable to watch the playoffs because it kills him.” Now he’d earned the right to go to a sure winner: a team with deep pockets, a stocked pond of talent, and the guts to push all in for five years. Effectively, that ruled out all but four teams: the Yankees, Dodgers, Cubs, and Astros. Not for Stanton the midmarket clubs riding a short wave up — the Clevelands and Colorados with a three-year window if everything broke in their favor. And no as well to longtime contenders who’d come to the end of their run — the San Francisco Giants and St. Louis Cardinals. If Jeter, the team president, wanted Stanton to expand his list, he was going to have to do some high-class groveling with his franchise player. And that, thought anyone who’d ever met Jeter, would be must-watch entertainment through Thanksgiving.
THE courtship of a dejected superstar is one of the hardest dances in sports. Done right, it’s a whisper-quiet, three-step waltz among the GM, the player, and his agent. “I’ll give you an example,” says Cashman, a disciplined cardsharp whose default face is a neutral stare. “Last winter, when I was dealing with Brian McCann, I called his agent [B. B. Abbott] to set the stage.” McCann, a slugging catcher with a no-trade clause in his five-year, $85 million deal, had been ousted from his spot by Gary Sánchez, the first of the Baby Bombers to arrive. “I told [Abbott] to tell Mac, ‘There’s a place on this team for you. You can be the backup and we’ll have the DH open, so if you’re cool with that, then we’re good. But if you want me to [talk] trades, I’m not going to disrespect you. You’ve earned the right to go where you like, so let me know what you want.’ ” Abbott talked to his client and got back to Cashman fast. “He said, ‘We appreciate you handling it this way, Cash. But hey, on the down-low, Mac’s not going anywhere west.’ ”
The Seattle Mariners were interested, but Cashman knew now not to engage them: the Braves and Astros were the only teams for whom McCann would waive his no-trade. Ever so softly, Cashman struck a deal with Houston: McCann (and most of his salary) for two green but electric starters pitching at the Single-A level. Both sides came up winners in the exchange — McCann earned a World Series ring in Houston, and Cashman moved most of his salary and used one of those kid pitchers in the trade he’d make for Stanton. His masterstroke: no one in the New York media got wind of the trade until it was almost done. “The last thing you want is Mac to hear from the papers, ‘the Yankees are shopping you,’ ” says Cashman. Then the “writers call and commentate
on the deal, and suddenly, you’ve got choppy waters.” Instead, McCann left “throwing bouquets our way,” glad for the chance to have been a Yankee.
CASHMAN, sitting at a Galleria lunch spot that passes for pan-Asian in Tampa, is a short, pale fellow with surprisingly broad shoulders and a thrumming disinterest in small talk. There is, in the fixity of his gaze and jawline, the set of a man taken lightly for too long. He’s one of those people who came to power fairly, on the strength of his smarts and sweat equity. To be sure, he used a family connection to land an internship with the Yanks while in college. But from the moment he got his foot in the door, there was no stopping Cashman on the come-up.
He was a baseball gym rat in college: too small to play for a prime-time program, he started all four years at Catholic University as its leadoff hitter and second baseman. He broke the school’s record for hits in a season and batted .348 his junior year. Not bad for a guy who stood five-seven and swung at every first strike. “The first pitch of the game was almost always a fastball — that’s why my average was so high,” he says. “I took advantage of what I knew was coming.” Perhaps because he speaks in a colorless burr and likes the back of the pressroom, not the front, he’s long been viewed as a kind of permanent temp, a substitute teacher who stuck around. For years, New York mistook him for an errand boy, the sad-eyed apparatchik catching hell from George Steinbrenner after a meaningless loss in April. He was paid less money than most of his peers, had smart trades sabotaged by The Boss, and appeared to survive where his forebears hadn’t because he didn’t punch back when abused. That last part was false, but he never troubled to correct it.
“He and George would have scream festivals for hours,” says Jean Afterman, the assistant GM of the Yankees, whose office at the new Stadium is next to Cashman’s. “I’d close my door but could hear them down the hall. Brian backs down from no one — that’s why George loved him.”
Cashman, like the three or four masters of his craft, is one part diplomat to two parts pickpocket. He can politely boost your watch and wallet and leave you thinking the heist was your idea. Jeter’s style, by contrast, is to dictate terms and expect you to glumly accept them. His first act after buying the Marlins was to pointlessly freeze out Stanton. He didn’t book the obligatory get-to-know-you dinner with his star at a stuffy rooftop steakhouse in Miami. He declined to call Stanton and offer congratulations when he was named the league MVP. And he never phoned Wolfe, one of the powerhouse reps in baseball, to ask about his client’s choice of destinations. “I was ready for the worst, which it was,” Stanton confided, looming at his locker in a pair of gold spikes after a workout in spring training in 2018. Like Judge, Stanton is one of those physical freaks you can’t properly appreciate on TV. It isn’t only his mass or stone-cut proportions, but the taper of chest and back to a tiny waist. There’s a quality about him that you sometimes find in art: grace and violence merged in random gestures. “If that’s how you want to treat someone, then there’s no playing nice,” he said of Jeter. “I had had more than enough.”
In late November 2017, he’d been given a diktat by Jeter. “It was, ‘Take this f---ing deal with the Giants or the Cardinals, or I promise you I’m trading everybody around you and you’ll be stuck here forever,’ ” said someone who was privy to those talks. Stanton had seventy-two hours to agree. He didn’t, per our sources, need them. Replying through his agent, he was River Avenue terse: No, and HELL no, goddamnit.
A thousand miles north, the Yankees looked on, appalled. “Derek’s done a good job of pissing everyone off,” said a member of the team’s administration. “I’m sure the guys at MLB now are scratching their heads, thinking, ‘What the f--k did we do by selecting him?’ ” Perhaps they looked at Jeter and mistook him for Magic Johnson, a hug-and-handshake natural who draws investors in droves and grows the worth of everything he touches. Instead, baseball’s bosses got a celebrity who didn’t seem to understand how relationships work at the executive level. “The press asked if Jeter felt the need to talk to Stanton, and he said, ‘No, that’s what my GM’s for,’ ” said the Yankee staffer.
WHILE Cashman insists that he liked Jeter as a player, it isn’t entirely clear that he means it. Or maybe it’s fairer to say that there were two Derek Jeters — the happygo-lucky kid from Kalamazoo who came up at twenty-one and seduced the sport with his cool-hand poise, that gift for the big play on the grand stage, and the thirtysomething Jeter who became somewhat hardened by fame. Treated like a civic institution in New York — worshiped by the faithful in their Jumpman-branded garb, teenage fan-girls rocking RE2PECT tank tops, and adored and protected by the tabloid scolds who trolled other stars on Page Six — he somehow remembered every slight and provocation. Jeter grew distant from writers who dared to notice that he couldn’t get around on a good fastball. His initial coldness toward Alex Rodríguez was as stark as it was cruel: there was that graceless moment in 2006 when a routine pop fly somehow fell between them. Jeter, hands on hips, glared daggers at A-Rod, emasculating him on national TV. That Derek Jeter wasn’t fun to general-manage — or to have playing behind you when you pitched. “When Andy [Pettitte] came back from Houston, there was a ground ball up the middle, and Andy’s like, ‘All right, that’s an out,’ ” says Cashman. “Next thing you know, it goes through for a hit and he’s like, ‘Crap, Jetes can’t get to those anymore.’ ”
Nonetheless, Jeter wanted to get paid like the player he’d been in his middle twenties. In the fall of 2010, he became a first-time free agent at the age of thirtysix. He’d had a bad year at the plate and a worse one in the field, but he demanded a max contract into his forties. Cashman pushed back, declining to bargain against himself. The terms he set and stuck to — $51 million for three years — pricked Jeter’s damaged pride. “Jetes sent messages through his agent that we were f---ing him when no one was willing to pay what we offered,” says Cashman. “I’m like, ‘How much higher do we have to be than highest?’ ” He invited Jeter and his agent, Casey Close, to go out and shop the deal. Jeter returned to the table smarting; no one had come close to the Yankees’ bid. Close even suggested a stark concession for his client: a piece of either the YES Network or the team. “At the meeting, Derek said, ‘What other shortstop would you want playing here?’ and I started rolling off names,” says Cashman. “I got, like, three names down and Casey said, ‘Stop, this isn’t productive.’ Then Derek got up and goes, ‘You guys finish this! I don’t want to go anywhere else, but I don’t want to be in here either!’ ”
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 pres-
sure 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, highreward 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 Cash- man 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 busi- ness, 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 chemistry.
“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?”