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Feb 15, 2024; Tampa, FL, USA; New York Yankees general manager Brian Cashman talks with media at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images Kim Klement Neitzel-Imagn Images

Brian Cashman Never Wanted Yankees GM Job

Originally posted on New York Yankees on SI
By Joseph Randazzo | Last updated Dec 7, 2025 12:23 PM ET

Brian Cashman has been in baseball a long time. His tenure with the New York Yankees began in 1986, and he took over as General Manager when Bob Watson was let go in 1998.

In a recent interview on the YES Network, the enigmatic GM revealed that he never wanted the job. Ironic, considering he has held the position longer than many Yankee fans were alive. Back then, the big fear was working under George Steinbrenner, then the team's owner.

"I never, never wanted to be the GM of the New York Yankees, I'll be honest. It's a very tough environment," said on Yankees Hot Stove. "And the GMs under George Steinbrenner, you know, didn't last very long. It was a year, a year and a half, maybe two years tops, and it was a difficult situation, no doubt about it.

"George Steinbrenner was a tough boss, and he didn't have much patience, and he was driven to non-stop success. And in baseball, you can't have success every day."

As Brian Cashman unveils he never planned to be the GM of the Yankees, @boblorenz, @JackCurryYES and @RealMichaelKay share their thoughts on his statements.

Watch LIVE: https://t.co/sWMqNZ0hci pic.twitter.com/jQY2rQFibw
— YES Network (@YESNetwork) December 4, 2025

Initial Success

Cashman's success as GM speaks for itself. He has never had a losing season, even in some of the darkest times like 2013 and 2014. Those years, the team managed to stay above .500 despite rolling out the shells of Vernon Wells, Ichiro Suzuki, and Alfonso Soriano.

Cashman also has four championships as GM. He won in 1998, 1999, 2000, and 2009. Still, the caveat is that he has yet to win a championship with a team that didn't feature the core championship players he inherited in Derek Jeter, Andy Pettitte, Bernie Williams, Mariano Rivera, and Jorge Posada.

Brian Cashman Needs to Win with His Own Team

For Cashman's biggest detractors to quiet down, he'll need to win a championship with his own players, finally. It would be damning evidence for those critics if the team can't win under captain Aaron Judge, who not only is the best hitter in the sport but has elevated himself to the pantheon of all-time great Yankees. Fair or unfair, that would be icing on the cake for a career that some would consider Hall of Fame-worthy already.

Every off-season, there's a chance to get that done, and right now, there are important decisions to make. One of which is whether the team should overextend itself to pursue Cody Bellinger, who has endeared himself to fans after Juan Soto walked in free agency and took a train to Flushing.

Bellinger ticks off the necessary boxes as far as defensive capabilities go and how his bat translated to Yankee Stadium, but there are some concerns. Does Cashman think it's worth using owner Hal Steinbrenner's money on a player whose peripheral numbers do not match his actual production?

Brad Penner-Imagn Images

Bellinger has a .254 expected batting average, .416 expected slugging, 88.3 MPH Average Exit Velocity, 7.5% barrel rate, and a 20th percentile 70.1 MPH bat speed. At 30 years old, there are a lot of red flags around Bellinger and the potential for him to be a serious regression candidate sooner rather than later.

Signing Bellinger isn't as easy a decision as it was in the 2024 off-season, when the plan was to throw the most money at Soto, knowing what he would give you for the next 10 to 15 years, and being a proper heir to their captain. Everybody understands Steinbrenner's spending habits, and if the Bellinger contract goes south, he will pull back on spending in future years.

What Cashman does to put a team around Judge while he is still in his prime and one of the best players in the sport will define him as a GM. If he fails, he'll be the guy whose winning years have an asterisk attached to them. Those critics will forever point out that he only won in this town with players from another regime.

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