Brian Cashman has been with the Yankee organization longer than he’s been without it. He was an intern by 18 and GM by 30—a meteoric rise for a dweeby non-athlete—and if the experts were to be believed, the whiz kid would have been gone by his next half-birthday, another casualty of The Boss’s famous rage. But for the past 15 years, amid sky-high expectations from ownership and fans, not to mention unprecedented media scrutiny, Mr. Cashman has presided over the purse strings of baseball’s most valuable franchise, and he has delivered the October goods, with four world championships and 14 postseason appearances on his résumé.
What’s more, Mr. Cashman has maintained the organization’s win-or-die mantra while fundamentally changing the way the Bronx boys do business. In the Moneyball age, Mr. Cashman has embraced advanced analytics without discarding the traditional scouting model. He has stood tall against two generations of Steinbrenners, the first family of New York sports. And now Mr. Cashman is preparing the organization for future success by spending smarter, building a top-tier farm system, and sticking to his no-apologies, unsentimental decision-making process, even as the current crop of Yankee greats winds down their hall-of-fame careers, showing the world that a man doesn’t need muscles to have balls.