The sky is blue, the water is wet, you never get anywhere on the Major Deegan, and Brian Cashman is the Yankees’ general manager. All these things are true. All these things will continue to be true.
The Yankees just conducted their end-of-season press conferences, and during the media sessions, Cashman confirmed to reporters that he had a new deal with managing partner Hal Steinbrenner, who was sitting with him: “We’ve agreed on a new contract, we just have to bang out some minor stuff on the back
end of it. But yeah, we’re locked and loaded.”
Cashman signed his previous deal after the 2022 campaign, and the four-year contract was set to expire at the end of October. But there was never any real doubt that Steinbrenner would bring him back. Cashman has Hal’s full, complete trust after decades of working together. Cashman has been with the Yankees so long that Hal was still in high school when the former first joined the organization as an intern before gradually ascending to an assistant general manager role and then the top job in February 1998.
Cashman is the longest-tenured GM in baseball, and it’s all but understood that the Steinbrenner family is comfortable with him in the job until whenever he decides to step back. Cashman will turn 60 in 2027; at 70, Phillies baseball head Dave Dombrowski is the oldest head of baseball operations in the league. So whether or not you like Cashman, he’s probably in it for the long haul.
Under Cashman’s watch, the Yankees have never finished with a losing record, which is not nothing considering that other good franchises around the league have had multiple awful seasons during his 29-year reign. If you ask people in front offices around the game, they are sincerely awed by that. But expectations are higher in the Bronx, and Cashman has added to the Yankees’ World Series trophy collection just once in the past 26 years. That was in 2009, which is already long enough ago that the only remaining active(-ish) MLB players from then (Max Scherzer, Andrew McCutchen, and Carlos Carrasco) could very well retire this offseason.
Cashman has also been steadfast in his support of the recently-confirmed-to-return Aaron Boone. Eyebrows were raised when the Yankees let Joe Girardi’s contract and expire and instead selected Boone to manage an upstart team that came within one win of a World Series berth in 2017, despite the latter having no coaching experience whatsoever
On my most generous day, I will acknowledge that for the most part, Boone has been a succesful regular season manager; they’ve made the playoffs in eight of his nine seasons, they’ve reached the ALCS on three occasions, and they at least snapped their pennant drought in 2024. By that measure, only the Dodgers’ Dave Roberts is better. However, they’ve also only won three AL East crowns, with midsummer swoons forcing them to accept Wild Card berths in multiple seasons this decade that have put them in bad position under the current playoff format, and while they could have overcome it anyway, they promptly fell pretty meekly to the actual AL East winners—the Blue Jays and Rays—in the ALDS. That’s to say nothing of the lapse in fundamentals that seem to occur annually at this time of year, which were ugly to watch in 2025 and 2026, but never more miserable than in that lone World Series appearance two years ago.
Much like Steinbrenner has been steadfast in his support of Cashman, Cashman has been resolute in his support of Boone. The 2027 season will be his 10th as big-league manager; no one in franchise history has been allowed to manage this long without a championship. Cashman did let Girardi go after a decade on the job when his contract expiring; perhaps he’ll do the same with Boone next year assuming another quiet October.
We won’t find out until then. All we know is that while Steinbrenner’s pointed comments about the offense mean that the Yankees’ roster won’t “run it back” to the same degree that they did last offseason, the management apparatus will indeed remain the same. So… huzzah for them, I guess.
