2. Gabe Pruitt
Career (Years): 2: 2007-2009
Championship Year(s): 2008
Career Stats: 2.0 PPG 0.8 APG 0.8 RPG
Many try to get to the NBA and fail in their attempt. Many who do make it don't end up staying long. It's the latter for Smilin' Gabe Pruitt, who only played two seasons for the Boston Celtics before relocating to the D-League. Being a fourth-string point guard isn't so much fun, but a 2008 NBA Championship ring isn't so bad a consolation prize, is it? Given that he got his nickname due to the frequency of his smiling, we doubt he's losing any sleep over it.