George Steinbrenner was many things. Above all, he was passionate. Passionate about his Yankees and, according to those who knew him as a Thoroughbred owner, equally passionate about horse racing. So it was no surprise that when he met a horse breeder and future Harness Racing Hall of Famer named John Cashman, the two hit it off. In 1986, Cashman leveraged the relationship to net a Yankees internship for his teenage son. That simple favor would be among the most consequential decisions in Steinbrenner’s
37 years at the helm of baseball’s most iconic franchise.
Brian McGuire Cashman
Born: July 3, 1967 (Rockville Centre, NY)
Yankees Tenure (as GM): 1998-present
Brian Cashman grew up in Washingtonville, NY as one of John and Nancy Cashman’s five kids. The young Brian excelled at baseball in high school at Georgetown Prep before starting for all four years at Catholic University of America. The same man who was introduced to the world at large as a scrawny, bespectacled wunderkind 10 years later was a top-notch leadoff hitter for the Division III university, setting school records in both hits and steals in a season.
Upon graduating, Cashman began a rapid rise through the Yankees’ organization. Despite his connection to Steinbrenner, it was the mercurial owner’s banishment in 1990 that accelerated his rise. Gene Michael, the baseball savant who stewarded the club in Steinbrenner’s absence, took a liking to the detail-oriented Cashman, promoting him all the way up to assistant general manager by 1992. “Brian knew everything going on,” Michael said of his protege. “Nothing slipped by.”
“He was a mentor to many people in this office,” Cashman would later say of the man everyone called “Stick.” “He did it with me and plenty others. If you were interested, he would give his time and expertise to try and train you. He was a remarkable individual who was impactful.”
Michael was replaced by Bob Watson before the 1996 season. After two seasons working under Steinbrenner, he resigned. On his way out, Watson recommended his 30-year-old assistant GM for the job. Whether due to that endorsement or Steinbrenner’s own read on his old buddy’s son, the Boss agreed to make Brian Cashman the second-youngest GM in MLB history.
There would be no training wheels for the big job. Cashman was handed the reins of a team with World Series aspirations and a star-studded roster, with Steinbrenner breathing down his neck. A couple of months into the ’98 season, the trigger-happy owner was having second thoughts and put out feelers to see if Michael would return and displace Cashman. “Brian can do it,” Michael reassured Steinbrenner. “Just give him time.”
Of course, that team would go down as one of the best in baseball history. A roster mostly assembled by Cashman’s predecessors won 114 games and a championship. In the ensuing years, which saw two more titles and another two pennants by 2003, Cashman made his mark, acquiring key contributors like Roger Clemens, Jason Giambi, and Hideki Matsui while signing international prospects including Alfonso Soriano and Robinson Canó. He also developed a reputation for tenacity and resolve. “He and George (Steinbrenner) would have scream festivals for hours,” Jean Afterman said, the assistant GM of the Yankees. “I’d close my door but could hear them down the hall. Brian backs down from no one — that’s why George loved him.”
After a few lean years, a retooled roster including Alex Rodriguez as well as the newly signed CC Sabathia, A.J. Burnett, and Mark Teixeira took home the Yankees’ 27th title in 2009. This time, while the Core Four of the ’90s dynasty remained, Cashman could take the lion’s share of the credit for compiling a roster that rose to the top.
The 17 years since that title have been a mixed bag. In 2010, Cashman famously entered into a very public salary negotiation with Derek Jeter in which he encouraged the captain to test free agency and reportedly indicated he’d rather have Troy Tulowitzki playing shortstop in New York. In addition to souring his relationship with the face of his team, that fracas — which resulted in a three-year, $51 million deal — turned much of the fanbase against their GM. It didn’t help that the Yankees failed to return to the World Series in the years that followed.
By 2016, with the wheels falling off, Cashman engaged in his first ever honest-to-goodness sell-off at the trading deadline. It would be a turning point, with the ’17 “Baby Bomber” Yankees making a rare underdog turn the following year. A young roster led by Rookie of the Year Aaron Judge and other homegrown talent developed under Cashman made a run all the way to Game 7 of the ALCS. And, while that 28th ring has remained elusive, the team has remained competitive in the interim, missing out on the playoffs only once and making it as far as the World Series in 2024.
Where does that leave Brian Cashman’s legacy? For one thing, with the longtime GM only turning 59, there’s no reason to believe that legacy is fully written yet. Dave Dombrowski, the Phillies GM who still appears to be at the top of his game, turns 70 this month.
When it comes to regular-season success, though, neither he nor any other active GM can approach Cashman, who’s overseen winning teams for each of his 28 seasons at the helm. The only other team without a losing season in the 2020s is the Dodgers, for whom Ned Colletti and Andrew Friedman have ably carried the torch since their last losing season in 2005. While the title draught in which the Yankees remain mired is a legitimate pain point, that much winning is not to be taken for granted; for an example of another big-budget team unable to put a consistently competitive product on the field, look no further than across town.
Cashman has also earned superlative acclaim from those who know the challenges of his job best. “Based on Brian’s accomplishments, I would make the argument that he is the greatest executive in the history of the sport,” longtime A’s GM Billy Beane said. “He has four championships and the longest tenure. It’s not unlike Tom Brady’s career, from an executive standpoint. He is the Tom Brady of GMs.”
Brian Sabean, a Cashman protege who went on to helm the Giants during three championship runs before returning to the Yankees front office, agreed. “Cash doesn’t get enough credit,’’ Sabean said. “If there was ever a Hall of Fame for executives in all of sports, he’s on top of the list. They understand what the expectations are (in New York), which are greater than everyone, and they keep on winning.”
In addition to his work in baseball operations, Cashman has a long track record of supporting his community. The Yankees-Stonewall initiative awards $50,000 in scholarships annually to graduating LGBTQ+ student leaders from each borough, something he’s called the “most meaningful work” of his career. He’s taken an active role in amplifying Spanish-language media, hosting an annual Hispanic Heritage Media Day. He also sticks his neck out both literally and figuratively while spending the night outside in a sleeping bag each winter, inviting mockery from his detractors to raise awareness for the nonprofit Covenant House. Cashman has also quietly built a singular legacy in elevating women in sports, including Afterman, Kim Ng (who Jeter would later hire as the first female GM in American male pro sports) and Rachel Balkovec, who he brought on as the first female manager of an affiliated team, the Low-A Tampa Tarpons.
Whatever your view of Cashman’s performance over his long career, his accomplishments speak for themselves, and his staying power in baseball’s toughest market has given him the chance to build on those achievements. While I’m sure not all of you will partake, I invite you to join me in wishing a happy 59th birthday to one of the most consequential figures in Yankees history.
See more of the “Yankees Birthday of the Day” series here.
