Accomplishments: 5x All-Star, Rookie of the Year (1994), All-NBA (2001)
Team(s): Warriors, Wizards, Kings, 76ers, Pistons
Currently: TNT analyst 

After persistent knee problems ended his career in 2008, Webber joined the broadcast crew at TNT. Mark Cuban made headlines earlier this month by tweeting that Webber is a "horrible analyst" and "does no homework before the game." We don't totally disagree but, by the standards of this list, C-Webb is doing pretty well for himself.