2. Kenny Anderson
Source: Iconosquare
Many people are wondering how to squander more than $60 million. In 2005, Anderson filed for bankruptcy. The start of his journey to bankruptcy began with eight cars and an estate in Beverly Hills. Having seven children and being divorced three times with child support on the table can definitely drain your bank account. To put the icing on the cake, Anderson lost his court-challenged prenuptial battle which allowed his first wife to walk away with half of his assets.