10. Kevin Youkilis: One Year, $12 Million, 2012-13 Offseason
Mom? Can you come in here? Cashman did it again!
Signing Youkilis to be a thorn in Boston's side didn't seem like the worst idea. He'd run aground in Beantown after an incredible stretch from 2006-2011 and found himself dealt to Chicago after 42 tepid games in 2012. Once in pale hose, he proceeded to hit .236 with a .346 OBP and 108 OPS+ in 80 games. Not bad!
Unfortunately, on a hefty one-year contract in New York, his back issues finally became too much to bear. The bare-faced ex-Sox hit .219 with a pair of homers in 28 games, the final 28 contests of his storied career.
He now runs a brewery in California called Loma Brewing Co., which is presumably where Aaron Boone drowned his sorrows after showing the Yankees 2004 ALCS clips between Games 3 and 4 against the Astros.