Cashman’s Burden

Illustration by Andy Friedman

Is being the general manager of the Yankees a fun job? There have to be days when it’s not, when it’s too exhausting and ridiculous to hang in. Even if it’s your dream job.

Brian Cashman started working with the Yankees, his favorite team as a child, when he was 19 years old, as an intern, smack in the middle of one of the franchise’s lowest ebbs. In 1986, his first year, Cashman watched his beloved Yankees miss the playoffs for the fifth consecutive season. They wouldn’t return for another nine years, until 1995; by that time, Cashman was an assistant general manager under Gene ­Michael. Three years later, at the age of 30, he was the general manager himself, a post he has held ever since. He is now 43—older, finally, than every player on his team.

Unless Cashman suddenly has a psychotic break and starts dropping truth bombs about the past 25 years of his life, we’ll never know what sort of hoops he had to leap through to survive two and a half decades in the Yankees organization. But it must have been hard: Save for some clubhouse staff, Cashman is the team’s longest-serving employee. You don’t make it that far in a business as chaotic and cutthroat as the Yankees without fighting, and winning, some wars.

His face shows it. Cashman doesn’t look the way the Yankees, as an organization, imagine themselves looking. The Yankees see themselves as Mickey Mantle: broad, corn-fed, hulking, perfect. Cashman is a small, nearly bald man with slumped shoulders, with a worried, harried, perpetually bemused “This job, man …” look on his face. The man has been through a lot. But he’s always been quieter, less high-profile than Billy Beane in Oakland or Theo Epstein in Boston; no one writes books about Cashman, and it’s impossible to imagine him sneaking away from reporters while wearing a gorilla costume. He is, in the purest corporate sense of the word, a manager.

Then, this winter, Cashman, whose contract is up at the end of this season, let his freak flag fly. His offseason comings and goings provided near-daily headlines. He publicly challenged Derek Jeter over his contract negotiations, leading to Jeter’s frustrated outburst at the press conference announcing his deal: “I was pretty angry about [the negotiations].” Unflustered, Cashman later said he imagined Jeter perhaps playing center field by the end of his deal, an act that might require a police order. Cashman also dressed up as an elf, bartended at a sportswriters bar wearing a mullet-­bandanna wig, and rappelled down a building in ­Connecticut. This was all for charity. It was also extremely strange.

The biggest needle-across-the-record moment was at the press conference where the Yankees announced the signing of reliever Rafael Soriano to a three-year, $35 million contract, far above market value. With Soriano wearing the sainted pinstripes for the first time, sitting just a few feet away, Cashman told the media that he “didn’t recommend” the deal, that it had been co-owner Hal Steinbrenner’s call. There is no more orchestrated event than a sports press conference: The ­primary goal is to project a unified front, whether it’s Randy Johnson pretending he’s happy to be here or James Dolan proclaiming that Isiah Thomas has nothing to do with the running of his team, honest. And here was Cashman telling a packed room that if he had had his way, the man the ­Yankees just introduced as their free-agent savior wouldn’t be here. It’s just a step or two removed from the public-address announcer’s saying over the Yankee Stadium loudspeakers, “Now pitching for the New York Yankees, No. 29, Rafael ­Soriano … unfortunately.”

The Yankees have always been a dysfunctional franchise, even when they were winning championships. There have always been disputes within the ranks, disputes usually settled by the heel of George Steinbrenner’s boot. It’s a little different now. This is not a major rift. This is not a systematic undermining. This is not a longtime employee snapping and going rogue. This is just … the way the Yankees are now.

The publication of Moneyball eight years ago changed the way the public thinks about baseball, statistics, business, and Michael Lewis. Within the world of baseball, it created the cult of the general manager. Beane cut such a striking, iconic figure—remember, Brad Pitt’s playing him in the movie—that baseball became a thinking man’s liar’s poker, a game that brainy college kids could master through logic, math, and moxie. Young guys like Epstein, Jon Daniels in Texas, and Jed Hoyer in San Diego became the stars, the new Wall Street whiz kids. If you couldn’t hit a curveball, you could still be a part of the game. You could run the game. When you think of the Red Sox or Rangers or Padres, you think of their general managers. Adrian Gonzalez or Josh Hamilton can be traded, but the young, handsome G.M. stays, the man behind it all, the wheeler and dealer, the lone rock star in charge. (2K Sports even made a G.M. video game; Beane and Cashman both consulted on it.)

Cashman, who will never be played by Brad Pitt in a movie, has always envied this; he’s close friends with Epstein and knows how revered Epstein is, not just in Boston but in the sabermetric baseball community as a whole. Boston is a little bit of a general manager’s fantasyland; Epstein has power and public renown in a great baseball city. Epstein can walk down the hall and talk to Bill James; Cashman is stuck running into Hank Steinbrenner on his smoke breaks.

This has been the fundamental quandary for Cashman since he took over. What kind of G.M. does he want to be? Does he want to be like Epstein, an all-powerful leader who is never questioned? Or does he want to be the G.M. of the Yankees, a multitentacled beast with a million masters, where you might be overruled on major personnel matters? Rumors about Cashman’s leaving have been swirling for years, mostly because of that apparent envy of Epstein, the desire for autonomy, the exhaustion from the daily trench warfare. His winter oddities only added to the speculation.

But Cashman has never said he wanted to leave, and when spring training began, he reemphasized he wants to stay with the Yankees, and the Yankees want him to stay. (The Yankees, per long-standing policy, don’t negotiate contracts until they end.) This is his dream job, after all, and it’s undeniably easier to be a successful general manager when your team has a nearly unlimited payroll.

That’s the weirdness of the situation, though. Remember: Cashman’s controversies this winter were about wanting to spend less money, not more. Most G.M.’s are constrained by a small payroll; Cashman acts like a man constrained by a large one. He would love to make the Yankees sleeker and younger, ignore expensive older free agents like Cliff Lee, make the team more nimble and flexible, the way their division rivals the Red Sox and Rays are. (Not signing Lee may hurt this year, with the Yankees’ rotation problems, but trust me, someday you’ll be happy the Yankees didn’t give a 32-year-old pitcher with a history of back problems $150 million over seven years.) He would love to do the job the way the other Young Turk G.M.’s do, the ones whose success and failure ride on their decisions in the short term and the long term.

Sad to say, though, the Yankees are the Yankees: Overpaying for expensive older free agents is their birthright. Cashman can construct a smart roster all he wants, but when the guys with the purse strings want to buy a player, who is the G.M. to say no? Why would he want to? It’s not his money.

This leads to the inevitable question: Who, in fact, is in charge here? The answer, of course, is: They all are. The Yankees are a billion-dollar organization, with a cable network and a new stadium and revenues flowing from every corner. That is too much for one man to handle. The whole notion of the job of G.M. is to have a finite amount of funds to be dispersed in as efficient a manner as possible; this is the whole point of Moneyball. But the Yankees have infinite funds, even if Cashman likes to pretend they don’t. So much so that when Steinbrenner and team president Randy Levine hand him a top-tier player like Soriano, he actually complains about the price. This is Cashman’s curse: He can run the team as smartly as he likes, but he’s never the one truly in charge. He is always going to be smaller than the team. That’s not what today’s G.M. is supposed to be.

Meanwhile, the Yankees get everything they want: a smart, steady hand at the till, trying to keep costs down and put a championship team on the field, a guy they know well enough that they understand when to step in and overrule to spend some money. It might seem like chaos, but it works.

And Cashman knows it. Which is why, as much as he might look out the window sometimes and wonder what life is like outside the only adult job he’s ever known, he’ll never leave. He has it pretty damned good here. We all do. If he needs to go slide down a building every couple of years to blow off some steam, more power to him. Nothing’s more stressful than your dream job.

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Cashman’s Burden