Brian Cashman has been at the helm of Yankee baseball operations since 1998. Hired in a role that sees frequent turnover, he has the third longest tenure of current MLB General Managers. But the Yankee GM job is unlike any other in professional sports. Cashman has spent over half of his time trying to appease the relentless George Steinbrenner. Cashman has spent even more time managing the egos that don the pinstripes. Needless to say, Cashman’s 24/7, 14-year job with the Yankee organization has been a thankless┬ácommitment. When Cashman’s contract expires on November 1, 2011, will that be his last day as a member of the New York Yankees?


Will This Be A Thing Of The Past?

There’s no disputing Cashman’s success with the Yankees. As General Manager, Cashman built teams have won four World Series Championships and six American League pennants. The Yankees have only missed the playoffs once under Cashman’s leadership. Over time, Cashman has shifted the Yankee dynamic from inking solely top free agents to developing younger talent in the minor leagues. In a five year span (2005-2010), Cashman’s improved the Yankee farm system ranking from the bottom third to the Top 7. That’s a┬ácommitment┬áto the future.

Despite Cashman’s successes, some huge obstacles have already begun to rear their ugly heads…

  • How will Cashman continue to deal with the decline of Jorge Posada? Will he be able to tell Jorge ‘no’ in the off-season?
  • Cashman will eventually have to move Derek Jeter down in the order and off of shortstop. Does he want to deal with this PR headache?
  • A-Rod’s inked through 2017. Will Cashman want to deal with that albatross of a contract?
  • Mariano Rivera is human and there will be a time when he’s done. Cashman may have to step in.

Cashman’s marriage with Yankee senior management and ownership hasn’t always been sunny. Cashman was prepared to leave following the 2005 season, but George Steinbrenner persuaded him to stay. Cashman and president, Randy Levine have gotten into some public spats over trades and free agent signings. Cashman was completely against the signing of Rafael Soriano and as of June 28, Soriano has only appeared in 16 games and spent over a month on the DL. Cashman has been given free reign as General Manager, but will he want to deal with Randy Levine interjecting? Would another organization probably just let Cash be Cash? Probably.

Ultimately, I think Cashman will be re-signed after the 2011 season. Cashman will be forever linked to the ‘Core 4’ and him inking one final three-year deal would seem fitting. Cashman will never have a better job than the Yankees