Twenty-eight years is a long time to be doing anything. It is a relative eternity to be the general manager of a North American professional sports team, where the median tenure for a GM in MLB is five-and-a-half
years. Since 1998, over a period that has seen multiple managerial changes and a handover of ownership, the one constant presence in the Yankees organization has been GM Brian Cashman.
There are two lenses through which to view Cashman’s 2025 job performance, each yielding starkly different evaluations. The time-worn viewpoint still adheres to the championship-or-bust mentality touted and crystalized by former owner George Steinbrenner, and through that lens Cashman has failed at his duties 24 times in the last 25 years, this season being no exception.
The other outlook accepts that said championship-or-bust mentality is a relic of the past — and in truth current owner Hal Steinbrenner has never publicly supported that mantra — and that Cashman has consistently fulfilled the directive set to him by Hal. They just concluded their 33rd consecutive winning season to make the playoffs for the eighth time in the last nine years, that streak of relative success maintaining sufficient fan interest such that season tickets continue to be re-upped and YES Network subscriptions continue to be renewed. The incoming cash flow remains uninterrupted, freeing the conglomerate to invest in outside areas that allow them to divest their money-making potential from the product on the field.
These are not your parents’ Yankees, nor indeed the Yankees that many of us grew up rooting for. Championship-or-bust has been replaced by good enough. Cashman’s position as GM is also unique to the other 29 men in that role around the league. The job is his for as long as he wants it. He is a part of the furniture, a close confidant of the owner whose greatest asset to his employer is the stability and consistency he provides, chiefly in terms of the bottom line he helps to bolster year on year.
And in fairness to Cashman, this season represented a relative departure from his usual modus operandi. Not since the winter prior to the 2009 season have the Yankees seen an offseason infusion of talent like the additions of Max Fried, Devin Williams, Paul Goldschmidt, and Fernando Cruz — at least not from a quantity standpoint. That aggressive approach to reinforcing the roster extended to the deadline, when Cashman traded for David Bednar, Camilo Doval and Jake Bird to prop up a faltering bullpen, infielders Ryan McMahon and José Caballero to address their defensive and base running woes, and bench bats Amed Rosario and Austin Slater to balance out what was the most lefty-heavy lineup in baseball this season. In certain circles, this might be considered an all-in attitude toward the 2025 season while in circles of a more Yankee persuasion, Cashman continued a years-long trend of acting in half measures while placing a higher priority on maintaining payroll flexibility, whether by eschewing multiple large contracts or hugging prospects who could (hopefully) become affordable cost-controlled major leaguers.
This final point of contention is where Cashman’s shortcomings are most stark. They clung to the ghost of Anthony Volpe’s admittedly excellent 2024 postseason showing like an easily offended pensioner might clutch her pearls, and the beleaguered shortstop rewarded them with 11 strikeouts in 15 ALDS plate appearances. Austin Wells’ defense remained excellent, but too often he couldn’t hit his way out of a wet paper bag. The regression of both these homegrown players should serve as a cautionary tale of relying on promoted prospects to form the foundation of the team, the Yankees poised to follow the same playbook with Jasson Domínguez, Spencer Jones, and George Lombard Jr. Cashman passed on multiple years of All-Star shortstops and traded away pretty much every other catcher in the minors — now he is stuck with Volpe and Wells. They also have to live with McMahon’s below-average bat at the hot corner for the next two (not inexpensive) years. Elite tier relievers like Mason Miller and Jhoan Duran were dealt at the deadline, but Cashman balked at the prospect cost — Bednar may have stabilized the closer role but Doval was erratic and Bird was demoted to Triple-A and left off the playoff roster altogether.
A team with a perennial top-three payroll should not be eliminated in the division series round. That being said, Cashman could not have predicted that his co-aces in Fried and Carlos Rodón — coming off sparkling regular season performances — would combine to give up 13 runs in 5.2 innings between Games 2 and 3 against the Blue Jays. He could not have predicted that regular season lineup extenders Bellinger, Giancarlo Stanton, Trent Grisham, and Ben Rice would collectively hit a frigid patch once the playoffs started. He could not have predicted that Williams and Luke Weaver would squander more leads than they helped preserve, leading to the Yankees losing the regular season tiebreaker to Toronto. However, such is the job of a general manager to anticipate pitfalls and have built contingencies and redundancies before the problems become problems — you know, like acquiring a Kyle Tucker the prior winter or adding an Eugenio Suárez at the deadline.
It is also only fair to acknowledge the very real wins by Cashman and his front office in 2025. The team tied for an AL-best 94 wins after most projection systems pegged them in the mid-80s range preseason. Rice emerged as a potential offensive cornerstone placing among the league’s elite in quality of contact and plate discipline. Cam Schlittler looks like the second coming of Gerrit Cole and has a chance to become their best drafted and developed starting pitcher since Andy Pettitte. Will Warren had his ups and downs, but finished first among rookie pitchers in innings pitched and strikeouts. It’s these type of success stories that underpin the continued — if misguided — faith in Volpe and Wells and the perhaps naive optimism that Domínguez, Jones, and Lombard can follow suit.
Cashman built Boone what the Yankees skipper called the best Yankees team he has managed in his eight years at the helm. In many respects, it was a better team than last season between the players added after pivoting from Juan Soto, the emergence of several rookies, and the bullpen upgrades at the deadline. Yet somehow the team squandered a seven-game lead in the division and was bounced from the playoffs by the team that leapfrogged them in the standings two rounds earlier than the 2024 campaign to which these comparisons are made, and the unenviable challenge of the coming months will be finding a way to reconcile these seemingly incompatible facts.
