Photograph By John Loomis for ESPN The Magazine
Cashman signs a new three-year deal with the Yankees in November 2011. During his tenure as GM, New York has made the playoffs 14 out of 15 seasons and won four World Series. Yet Cashman has never earned executive of the year honors. "I'll take my five World Series rings that Ive been associated with, and that trumps any executive award that anybody can throw at me," Cashman told Buster Olney during their televised interview on ESPN.