9. Scottie Pippen
Source: Iconosquare
Pippen, a famous NBA player, has not yet filed bankruptcy, but reports suggest he is well on his way. Over the course of his basketball career, Pippen made $120 million. Scottie blames a lot of his financial misfortune on law firms who mismanaged his money. His affair with bankruptcy in the future certainly doesn’t have anything to do with the $4 million Gulfstream jet Pippen purchased in 2001 he barely got to experience because it was grounded.