Appropriately named Cashman has the enviable job of picking players for the Yankees, and the unenviable job of answering to the capricious Steinbrenner family.
Cashman grew up in Lexington, Kentucky, where his father, a horse trainer, got to know George Steinbrenner, a fellow race horse enthusiast. During the summer of 1986, Cashman started with the team as a college intern; after graduation, he was hired full-time, moving up to the position of assistant general manager in 1992. In 1998, at just 30, he became general manager and senior vice president. Cashman's appointment as GM coincided with the start of the Yankees' golden years—they nabbed three straight championships from 1998 to 2000 and reached the World Series again in 2001 and 2003. Much of the success, of course, stems from having the largest payroll in baseball, which has enabled the team to lock in some of the best talent around. But Cashman's also earned credit for his financial savvy. It was his idea, for example, to move many Yankees home games to 7:05pm from 7:30pm to maximize concessions sales. Although Cashman's been criticized for shelling out big money for superstars that underperform once they throw on a Yankee uniform—he was almost ousted in 2007 with Joe Torre after a long (for the Yankees) championship drought—the 2009 World Series win gave him the career resurgence he desperately needed. [Image via Getty]