2. Brian Cashman
Cashman must be a robot, because there’s no way any mortal human could survive being GM of the Yankees for 25 years. It’s a miracle he was never fired, but then again, he hasn’t given ownership much reason to let him go.
Cashman’s resume speaks for itself, of course. He’s built four World Series champions (1998-2000, 2009) during his time at the helm and New York has made the playoffs virtually every year. The Yanks have never even had a losing season under his watch, much less finished in last place (although that could change this year).
If anyone could use a change of scenery, it’s Cashman. He has to be getting at least a little tired of the job by now after a quarter century. He’s already plenty familiar with the Red Sox from sharing the same division with us, too, so it’s not like we’d be bringing in a total outsider.
And surely he must be sick of the Steinbrenners by now? If he really wants to stick it to them and all the Yankees fans who’ve been calling for his head this year, jumping ship and going to Boston would be the best way to do it.
If you can make it in New York, you can make it anywhere. Well, Cashman has certainly made it there, cementing his legacy as a Hall of Fame executive whenever he decides to retire.