11. Allen Iverson
You know what they say: the bigger they are, the harder they fall. This phrase, we think, applies to Allen Iverson, who used to be one of the biggest names in the NBA. Over the course of his decorated playing career, Iverson managed to amass a fortune of close to $160 million. However, a number of troubles for the former baller, mostly in the form of substance abuse and gambling, have drained his once-mighty bank account.