As Yankees’ General Manager, Brian Cashman of Darien has what many consider to be a dream job, but keeping everybody happy — especially the “Boss” — makes it demanding too.
Grace Cashman, age seven, has everything planned. When her daddy, Brian, leaves his current job, his cellphone will be laid out on the driveway of his family’s Darien home. Her mom, Mary, will climb into their SUV. Then Grace and her brother Teddy, age two, will watch as the auto transforms the phone into cellular pâté.
“She’s not joking,” Mary says. “She’s serious.”
Not that Grace doesn’t like it that her father is general manager of that most legendary of sports franchises, the New York Yankees. But that cell- phone can be distracting. When she’s got him locked in a snowball battle on some winter’s day, he’s simultaneously carrying on a conversation with some agent or a scout or a man he calls “the Boss.” You try making a snowman with somebody who’s trying to make Johnny Damon a Yankee at the same time. It’s hard.
“My winter is harder than my summer,” Brian notes. “It’s all a lot of work, but the winter is that much more, going head-to-head on free agency, arbitration and trades.”
But while his pinstripe dedication may annoy Grace, it pleases others, chief among them the Boss, a.k.a. George Steinbrenner. In his thirty-three years as the Yankees’ principal owner, Steinbrenner has gone through about as many general managers as Spinal Tap has drummers. Only Cashman, in his ninth year as GM and just signed to a new contract, has lasted this long. It probably helps that the Yanks have finished atop the American League East every season he has been there, have won three World Championships in a row, and are widely considered the class of baseball in 2006.
“Brian, from what I’ve seen, is highly respected by the people in his profession not only for his business acumen but also for his ability to work for George Steinbrenner, who is extremely difficult to get along with and apparently remains as volatile as ever,” says ESPN commentator Jeremy Schaap. “How he’s managed that relationship has been very impressive over the years.”
Joe Torre, the Yankees manager since 1996, says Cashman has “his finger on the pulse” and a “non-stop work ethic.”
“It’s like a play on Broadway, and he’s the director,” Torre says of Cashman.
Just because it’s a dream job doesn’t mean it’s been easy. Even in Cashman’s first three seasons with the Yankees, 1998–2000, when the team won back-to-back-to-back World Series contests, Steinbrenner’s reported rages made tabloid headlines. Since 2000, the Yankees have reached the World Series twice, losing to the Arizona Diamondbacks in 2001 and the Florida Marlins in 2003. They have won their division every season since Cashman became the surprise choice to succeed Bob Watson just before the 1998 season. That’s an unprecedented run of success even for the Yankees, but it’s not enough for Steinbrenner or the team’s success-spoiled fan base. Nor is it for Cashman.
“Most of the pressure he puts on himself,” Mary says. “He wants to win. He wants to win for the team, and he wants to win for Steinbrenner.”