Brian Cashman, the GM of the New York Yankees, may be the worst ever at the best job in the world. Which is why he’ll inevitably fail this year in his shameless attempt to buy a World Series.
The GM of the New York Yankees may be the worst ever at the best job in the world. Which is why he’ll inevitably fail this year in his shameless attempt to buy a World Series.
By Matt Taibbi
There are some jobs in this world that are really, really hard to screw up. If the title on your business card reads something like “Mrs. Aristotle Onassis” or “Mrs. Prince Rainier of Monaco” or “Mrs. Bald-and-Sweaty International Arms-Trading Gazillionaire Adnan Khashoggi” — if you need a team of Sherpas just to carry the credit cards issued in your name — it’s probably not unreasonable to assume that you know a thing or two about shopping.
Of course society is going to give you a pass if you don’t know a whole lot about more useful stuff, like how to feed the poor, calibrate ground-to-air missiles, or dredge the Duluth shipping canal. But if you’re six or seven years into one of those marriages and you still don’t know how to buy a fur coat or a Fendi handbag, we’re all going to have to assume you’re completely brainless, a cabbage in heels.
And would you blame us, Brian Cashman? Because objectively speaking, the job of New York Yankees general manager should be the single most failure-proof position not only in sports but in all of human society. Giving a normal, red-blooded, pattern-baldness-suffering American male access to the Steinbrenner fortune and asking him to buy 25 baseball players a year in an unregulated market is no different, in any meaningful way, from handing Sarah Jessica Parker a blank check and asking her to fill a three-bedroom apartment with shoes and dresses. And we’re not even asking her to get good deals. All we ask is that the outfits match.
It’s obscene that a job like this even exists. But for someone to have this job and fuck it up is just appalling, the kind of gross disrespect for our own good fortune that makes it hard for us Americans to look the Third World in the eye. What Brian Cashman has accomplished as GM of the Yankees over the past few years, in turning a perennial World Series champ into a third-place also-ran, is like walking into a backstage party for Led Zeppelin with a two-pound bag of coke and a 28-inch penis and failing for a whole night to get laid.
Cashman managed to discover the one avenue through which limitless money and power under the current Major League Baseball rules can be a competitive disadvantage. He found that if you pack your roster from top to bottom with pathologically needy, egomaniacal, paranoid megamillionaires aged 30 and up, you can more or less permanently block the development of the choice, hungry, 25- to 30-year-old talent group that serves as the core of virtually all winning baseball teams.
What’s even more interesting is that after implementing this formula so successfully that the Yankees fell behind a Cape Cod League team called the Tampa Bay Rays last year, Cashman decided to double down on his strategy — opting to plug his team’s now-gaping holes by signing another $441 million in new megamillionaire free agents, with the bulk of that money going to the superstar trio of C.C. Sabathia, A.J. Burnett, and Mark Teixeira. With his shameless, blatant attempt to buy a World Series with a half-billion-dollar shopping spree at a time when the rest of the country is scrounging under the couch cushions for ramen money, Cashman has laid the foundation for 2009 to be maybe the most entertaining year for non–Yankees fans in the history of baseball. We are all trailing six car lengths behind, waiting for the pinstriped truck to jackknife and explode in a giant conflagration of scandals and finger-pointing. In an age when huge, irresponsible financial bets have brought Western civilization to the edge of collapse, Cashman’s Yankees are perfectly positioned to become an object lesson in everything that has gone wrong with American society in the past eight years or so.
Brian Cashman has kept his job in baseball over the years because he is masterfully good at just one particular thing: choosing sides in exploding Yankee scandals. Back in 1998, when he was elevated to general manager at age 30 (he joined the organization as an intern at 19), the assumption was that he would be there in title and that George Steinbrenner would be the guy making all the major decisions. Which sounds like a shitty deal for Cashman, except that, for the next 10 years or so, he could safely whisper to his buddies in the media that all the Yankees’ bad decisions were really made by the loony man above him. (Cashman has probably shoplifted a good two or three years of extra job security just by being one of the few people in the Insane Yankee Clown Posse to always feed the ravenous New York sports press.) He’s sort of like the Democratic Party in that he has managed to convince his fans that he was actually against deals he voted for/was in on from the beginning, and vice versa. Most Yankee fans believe Cashman didn’t really want to fire the revered Joe Torre and didn’t really want to sign Japanese special-needs student Kei Igawa and didn’t really want to acquire wall-puncher Kevin Brown or anger addict Randy Johnson or Jaret Wright or José Contreras or Jason Giambi or any of the other overpriced, underperforming free agents who soiled the hallowed grounds of Yankee Stadium over Cashman’s tenure.
The story we’re supposed to buy is that Cashman deep down inside is really a Theo Epstein–style GM who values internal player development and homegrown pitching (just like the Democrats deep down inside were against the war in Iraq) but just hasn’t been allowed to do his thing because Steinbrenner or his equally loony sons are always overreacting to losing spring training games and forcing Cash’s otherwise steady hand.
Cashman apologists would have the world believe that every time Yankee ownership sees David Ortiz hit a home run or James Shields pitch a complete game, this poor, unassuming, numbers-crunching GM gets an angry phone call from Steinbrenner’s Florida palace (in the public imagination, a massive palm-lined subtropical resort not unlike Pablo Escobar’s lavish Medellín spread) and is ordered to immediately go forth and buy a 10-figure free agent from Scott Boras to quiet the doddering Boss’s temporary attack of Player Envy. And right then and there Cashman’s sound, fiscally conservative 10-year plan to build around Austin Jackson, Phil Hughes, and Andrew Brackman (it was Ben Ford, Ryan Bradley, and Craig Dingman once upon a time) goes up in smoke.
Year after year this legend is perpetuated by a mysteriously persistent series of rumors/revelations in the press about both Cashman’s career choices and the inner workings of the Yankee empire. We seem to hear constantly from plugged-in baseball types like Fox’s Ken Rosenthal and SI’s Jon Heyman that Cash is in consideration for a GM job in a place like Washington, DC (the rumored destination in 2005) or Seattle (the rumored destination last fall), where he presumably wouldn’t be bogged down in organizational disputes and would be able to have real freedom in personnel decisions. And each time we are reminded just how much of a genius Cashman is, his wunderkind reputation still riding off the fumes of those world championships his first three seasons — championships that, in reality, were seeded years earlier by former Yankee personnel legend Gene (Stick) Michael, a man who actually considered chemistry when building teams. Interestingly, these whispers always seem to be floated just prior to Cashman signing a rich new long-term deal with the team that does bog him down in organizational disputes and doesn’t give him total personnel freedom, the Yankees.
The net effect of all of this has been to inoculate Cashman from responsibility for any and all Yankee misfortunes. It’s not unlike an athlete who lets you know before the game that his arm hurts; if he gets lit up for seven runs in three innings, you know why. If he throws a shutout, he’s a hero. That’s why it’s considered pussy to mention that your arm hurts before a game. It is pussy. If you’re well enough to play, zip it. And if you spend $200 million by day on aging steroid-jacking free agents with steel gloves and anger-management disorders, don’t call Sports Illustrated columnists by night and tell them you wish you could just go with the kids the way they do in Tampa or Oakland.
At least there’s no more of that bullshit this season. Last year at this time, Cashman made one of his few Machiavellian political mistakes by publicly opposing a high-priced trade for Johan Santana and instead hitching his career wagon to a youth movement led by Hughes, Ian Kennedy, and Robby Cano. Hughes-Kennedy went 0-93 for the season, and Cano spent half the year being the slow half of a double-play combination that included Derek Jeter, who these days practically needs a walker to cover the hole at short. The Yanks missed the playoffs, and Cashman, rather than going off as threatened to the paradise of a $60 or $50 million budget in Pittsburgh or Kansas City or DC, promptly re-signed a rich deal with the Yanks and abandoned the one-year youth experiment to sign the Sabathia-Burnett-Teixeira trio for a total of 14 trillion dollars. The Yankees and their GM are finally standing together on the same plank, going all-in with a full squad of soulless all-star mercenaries bought on the open market at hostile-takeover prices.
The reason every baseball fan in the country outside of New York is rooting against them is the same reason everyone rooted for the Tampa team last year. It’s not just that people resent the idea that the thrill of a championship victory can be bought; it’s the way the Yankees bought their talent that grosses people out.
Specifically, they overpaid. They spent many millions more than other teams would have paid for guys who clearly preferred, all things being equal, to be somewhere else. Teixeira probably wanted to be in his hometown of Baltimore. Sabathia would have liked to go back to Milwaukee or home to the West Coast, but definitely in the National League, where he’d get to hit. Burnett, he’s a guy all of baseball knows would rather play in a low-intensity/small-market environment like Toronto.
They all made a show of preferring some other situation before quietly, somberly almost, taking the big money and going to New York. Basically, Brian Cashman hired a team full of Brian Cashmans, i.e., guys who passed up the girl they really liked to marry the Boss’s bucktoothed, cross-eyed daughter. They might do their nightly duty in the sack, but they’re not going overboard. They’re not buying her flowers on the way home from work or taking her on surprise trips to Paris for Valentine’s. And their excuse for being crappy husbands is built into the deal: They never really loved her to begin with.
Which is why at the first sign of relationship trouble — the first six-game losing streak in May, the first whispers of a Joe Girardi firing in June — they will all scatter like rats to the far corners of the Yankee clubhouse and start making cell-phone calls to their agents and whispering to the press. That’s the way it’s always been with high-priced free-agent teams, from the Dan Snyder Redskins to the Malone-Payton Lakers to the Yankees of the A-Rod era.
And unless the karma gods decide to spend the summer in a diabetic coma, it’s almost certainly what’s going to happen to this year’s Yankees. God, is it going to be fun to see. Nothing is more entertaining than watching the rich choke on their own greed.
This article originally appeared in the May 2009 issue of Men’s Journal.