​In Cleveland, Ohio, Yankees General Manager Brian Cashman attends team batting practice before Game 3 of the American League Division Series at Progressive Field on October 15, 2022. (Photo by William Perlman/Newsday RM via Getty Images) | Newsday via Getty Images. George Steinbrenner was many things, but above all he was driven by passion—unyielding devotion to the Yankees and, to those who knew him as a Thoroughbred owner, a deep love for horse racing. So it wasn’t surprising that when he met horse breeder John Cashman, a future Harness Racing Hall of Famer, the two hit it off. In 1986, Steinbrenner used that connection to land his teenage son a Yankees internship. That simple favor would become one of the most consequential decisions of Steinbrenner’s 37 years at the helm of baseball’s most iconic franchise.
Brian McGuire Cashman, born July 3, 1967, in Rockville Centre, New York, has served as Yankees GM since 1998. Cashman grew up in Washingtonville, New York, as one of John and Nancy Cashman’s five children. He excelled in high school baseball at Georgetown Prep and played for all four years at the Catholic University of America. The once-portrayed scrawny, bespectacled wunderkind had become a premier leadoff hitter at Division III Catholic University, setting school records for hits and steals in a season.
After graduating, Cashman quickly ascended through the Yankees’ ranks. Despite his tie to Steinbrenner, it was Steinbrenner’s banishment in 1990 that accelerated Cashman’s ascent. Gene Michael, the baseball savant who ran the club in Steinbrenner’s absence, admired Cashman’s attention to detail and promoted him to assistant general manager by 1992. “Brian knew everything going on,” Michael said of his protégé. “Nothing slipped by.” Cashman later reflected that Michael had mentored many people in the office, including him, offering time and expertise to those who showed interest. “He was a remarkable individual who was impactful.”
Michael was replaced by Bob Watson before the 1996 season. After two seasons under Steinbrenner, Watson resigned, and on his way out endorsed Cashman as the next GM. Whether due to that endorsement or Steinbrenner’s own read on his former ally’s son, the Boss decided to make Brian Cashman the second-youngest general manager in MLB history. There would be no training wheels for this job: Cashman inherited a World Series–contending team with a star-studded roster, while Steinbrenner watched closely. A few months into the 1998 season, the owner briefly considered contacting Michael to see if he would return and replace Cashman, but Michael reassured him, “Brian can do it. Just give him time.”