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Cashman's Burden

Being the general manager of the Yankees is his dream job. So why does he seem to want out?


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.)


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