
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.
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.
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."
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.
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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