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.