Inside The Pinstripes

Brian Cashman Has No Timetable for Yankees Departure

For anybody hoping Brian Cashman’s time with the New York Yankees will be up soon, not even he is sure when he’ll be leaving.
Jun 20, 2023; Bronx, New York, USA; New York Yankees general manager Brian Cashman on the field during batting practice before a game against the Seattle Mariners at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Jun 20, 2023; Bronx, New York, USA; New York Yankees general manager Brian Cashman on the field during batting practice before a game against the Seattle Mariners at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

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Brian Cashman has been with the New York Yankees since 1986, when he broke in as an intern. After a decade, he rose to the position of general manager and hasn't looked back. Nobody in the organization today has seen up close more ups and downs, or peaks and valleys, than him, outside of Hal Steinbrenner.

New York Yankees manager Joe Girardi (28) and general manager Brian Cashman
Feb 23, 2016; Tampa, FL, USA; New York Yankees manager Joe Girardi (28) and general manager Brian Cashman (right) talk in the bullpen at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-Imagn Images | Kim Klement-Imagn Images

Grading Cashman's successes and failures really depends on who you talk to. Fans and media members of a certain age may consider what he's done since 2009 a failure, given the weight of the franchise and how it has been defined by its past success. The Bill Maddens of the world watched firsthand what Yankee excellence is, and this version of the team might be perplexing to fathom for him, even if he comes to everything with an unfiltered reporter's lens.

Others on the outside might feel the complete opposite sentiment from the brash portions of the fanbase and media. Compare what Cashman has done to other franchises like the New York Mets, Pittsburgh Pirates, or Cincinnati Reds — even with the caveat that the team hasn't won since Barack Obama's first term in office — and anybody around those teams would do anything for the type of sustainability he has provided. Steve Cohen has said as much, and his wallet has done a lot of the talking.

Now, with more than 28 years under Cashman's belt at the position, outside of figuring out when that next championship run will be, the big question surrounding Cashman is how long he'll be staying with the Yankees. It feels as if he has carte blanche at this point to leave when he pleases, and no playoff loss or championship drought is devastating enough for him to be ousted from his position.

What's Next for Cashman?

When asked by the New York Post's Mark W. Sanchez how long he thinks he has, Cashman gave a simple answer.

"I have no idea," he told him.

While Cashman has no timetable for his departure, he has given some thought to life outside of baseball, even if his singular focus is on the present, as he told Sanchez multiple times in their interview.

"I'm really happy and proud to be a part of this great game of baseball and be associated with arguably the greatest franchise in sports in the world," Cashman continued. "I don't take that for granted. But at the same time, I have a lot of passions and loves. I follow a lot of other sports and [have] nonsports passions and stuff like that."

Leaving on His Terms

If there's a perfect ending to a Hollywood script for Cashman to leave on, it would involve a 28th championship, which has eluded him since 2009. The thing about a title now is that it would be a roster that is completely his. His previous championship involved a core assembled by Gene "Stick" Michael, who completely revamped the organization after some lean years.

ew York Yankees shortstop Derek Jeter
Nov 4, 2009; Bronx, NY, USA; FILE PHOTO; New York Yankees shortstop Derek Jeter (center), Jorge Posada (left), and Mariano Rivera (right) look at the championship trophy after beating the Phillies to win their 27th championship. The Yankees beat the Philadelphia Phillies 7-3 in game 6 of the 2009 World Series at Yankee Stadium. Mandatory Credit: Robert Hanashiro-Imagn Images | Robert Hanashiro-Imagn Images

The Derek Jeters and Jorge Posadas of the world have long since retired. His captain is Aaron Judge, and the best player in baseball is probably the only person more desperate for a championship than Cashman himself.

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Published
Joseph Randazzo
JOSEPH RANDAZZO

Joe Randazzo is a reference librarian who lives on Long Island. When he’s not behind a desk offering assistance to his patrons, he writes about the Yankees for Yankees On SI. Follow him as @YankeeLibrarian on X and Instagram.