8. Evander Holyfield
Source: Iconosquare
Everyone knows boxing professionals can make a substantial amount of money. Holyfield was one boxer who seemed to have it all. Aside from making millions from boxing, he had endorsements for many things, such as video games, grills and sodas. Seems like everything worked in his favor right? Wrong! Even with approximately one quarter million dollars in profit, he still filed for bankruptcy. How is this possible? Having 11 children can drain you financially in an instant. Holyfield’s home was foreclosed upon in 2008.