The Yankees will face a crossroads in the next month. Brian Cashman has been the team's general manager since February 1998, and since the fall of 2005 Cashman has run the baseball operations, focusing on rebuilding the team's farm system. His contract expires at the end of October, and the Steinbrenner brothers have made it clear that they'd like to keep him.
But Cashman could choose to leave to pursue another job, either in Philadelphia, Seattle or some other place. If he does so, the executive who would replace him would face extraordinary pressure to deliver a championship as soon as possible. Under those circumstances, it might be difficult for the Yankees to continue reconstructing their farm system -- so Cashman's decision could have an incredible impact on the Yankees' future.
Imagine if Cashman sat down at his kitchen table with a notepad, and drew up two columns -- one listing the reasons to go, and the other the reasons to stay.