9. Dave Littlefield, Pittsburgh Pirates: No GM had more of a knack for trading great talent and getting so little in return. From getting next to nothing for established stars like Jason Schmidt and Aramis Ramirez, selling low on players who blossomed elsewhere like Chris Young and Oliver Perez, to trading for Matt Morris and his $9.5 million contract in 2008, Littlefield's six-year track record will go down as one of the most extraordinary in MLB history. Only Sandy Koufax's run in the '60s was more impressive.
10. Cam Bonifay, Pittsburgh Pirates: Going from Cam Bonifay to Dave Littlefield as your GM is like getting over a raging case of the clap, only to learn you have leprosy.