Angell’s description of the Yankees appeared a year before Steinbrenner and a group of investors bought the team from CBS for $10 million. Four years later, they won the first of back-to-back World Series. They wouldn’t win another one for 18 seasons, the longest such drought since their first championship, in 1923. To keep the Yankees relevant, Steinbrenner brought back Billy Martin, the manager who won the 1977 World Series, fired him, hired him again, fired him again, hired him again — five round trips in all in the 1970s and ’80s. He packed his roster with All-Stars. The annual additions — Dave Winfield, Don Baylor, Rickey Henderson — seldom fit well into the existing contours of the roster, but they made the team impossible to ignore. “He commanded the universe of baseball to say, ‘You’ve got to pay attention to the Yankees at all times,’” Cashman says. “I mean, who else could take the Yankees, with all their history and championships, and build on them and somehow improve them and magnify them as a commodity?”
But the price of Steinbrenner’s extraordinary efforts is one that Cashman continues to pay. “If there are 10 million Yankee fans in the metro area, that mentality has created 10 million George Steinbrenners who are now buying the tickets and calling the talk shows,” he says. “He created an atmosphere of expectation and demand. He weaponized the environment to a level of need, desire, expectation that is impossible to meet.” In 2023, for the first time in seven years, and only the fifth time during Cashman’s tenure, the Yankees didn’t make the playoffs. They didn’t come particularly close, missing out by seven games, but still managed a winning record. “But you’d think we lost 100 games,” he says. “I mean, it was ugly and hostile.”
Nevertheless, Cashman keeps a photo of Steinbrenner mounted on the wall of his office. “I wouldn’t be here without him,” he told me during one of our meetings there. His parents, John and Nancy, knew Steinbrenner from the horse-racing business. In 1986, Cashman was a freshman playing second base at Catholic University in Washington. He had few interests outside of baseball. “Other kids would go to the beach in the summer,” Nancy Cashman told me. “Brian just wanted to go to the ballpark.” When he ran out of money on his team’s spring break trip to Florida, his father, whose Kentucky-based company owned the Pompano Park racetrack, told him to meet up with an executive there who would give him what he needed. The executive, who happened to be wearing a Yankees’ championship ring, said that Steinbrenner, who kept horses there, was a close friend. That led to a summer internship with the Yankees.
From then on, Cashman’s interactions with Steinbrenner were much the same as everyone else’s. He incurred that volcanic wrath when he made a mistake, and occasionally when he didn’t. “Cashman was always the scared rabbit,” the longtime agent Scott Boras told me. “I mean, George would run him ragged.” And when Steinbrenner wasn’t yelling, he was often disdainful. “It was definitely a hostile work environment,” Cashman says now, yet he was able to thrive. “It was normal to me.”