He said that he was an unlikely candidate for the Yankee GM's office, however. "I grew up as a Yankee-hater — I was a Los Angeles Dodger fan, and I hated the Yankees because they always beat the Dodgers," he said. While a student at the Catholic University of America in Washington, Cashman, then 19, began with the Yankees as an intern. "I did just about anything, without question — I'd run stats, I'd pick up the GM's wife at the airport, I'd work with stadium security. Whatever they asked me to do, I would do it."

Despite being the "low man on the totem pole" in the Yankee organization, he said that he "loved the work because it was baseball."

He found himself getting one promotion after another. "Not surprisingly, there was a lot of turnover — the opportunities above me kept popping up."