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rewrite this title Yankees’ postseason exit should signal end of Brian Cashman era

October 8, 2025
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rewrite this title Yankees’ postseason exit should signal end of Brian Cashman era
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With the Toronto Blue Jays knocking the New York Yankees out of the postseason on Wednesday night, it’s clear that the Yankees, when the October lights hit, are once again not among the elite teams in Major League Baseball. No one is more to blame for that than senior vice president and general manager Brian Cashman.

Cashman is the longest-serving GM in Yankees history and has the longest tenure among his MLB peers, serving in his role since 1998. During that time, the Yankees have racked up more than 2,500 regular-season wins and earned four World Series titles.

It’s an impressive history, but it’s also one that should come with a bit of nuance as well.

The last World Series win for the Yankees came in 2009, and the storied franchise has been back to the Fall Classic just once since then, falling short against the Los Angeles Dodgers last year. Around that one World Series appearance has been numerous postseason disappointments with talented teams and hefty payrolls, including this year’s Yankees team that has the fourth-highest active payroll among all 30 MLB teams, per Spotrac.

Trade-deadline failures should doom Yankees’ Brian Cashman

Mistakes made at this year’s trade deadline could well have been the final straw for Cashman’s reign. Trading for relievers David Bednar, Jake Bird and Camilo Doval to strengthen the back end of the bullpen has backfired horribly for New York, with Bird lasting just 2.0 innings in a Yankees uniform before being demoted to Triple-A.

While Bednar has rounded into form recently, posting a 2.08 ERA in his four postseason appearances covering 4.1 innings, none of Cashman’s other trade-deadline acquisitions have made serious impacts or completely handled the two positions were the Yankees were struggling (third base and relief pitching).

Seeing the weaknesses is one thing. Being able to fix them is another, as Cashman has proved again this season is easier said than done.

Cashman’s contract runs through next season, and it would be easy for the Yankees just to ride it out for one more year and hope everything falls in place for another World Series run. However, if the Yankees truly want some kind of change, acting now rather than waiting could signal a new direction for the franchise in time for what could be a pivotal offseason.

For most franchises, Cashman’s track record would be untouchable. But for the Yankees, where the standard is championships, 15-plus years without a title despite massive spending represents failure to meet organizational expectations. A fresh perspective might be exactly what’s needed for the Yankees to return to championship glory.

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