12. Jason Caffey

-cash blown: $29 million

His estimated career earnings in NBA was thirty million dollars. Surprisingly Jason Caffey was able to blow all this money and went from riches to rags. He won two championships with the Chicago Bulls. Jason is a father of ten children by eight different women.

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Despite making millions in his NBA career, he was arrested in the year 2007 for failing to appear in court for a child support hearing. In August, he filed for bankruptcy in Alabama to get the court off his back for child support. He is in debt for nearly two million and has approximately 1.5 million in assets in business ventures. At least according to the bankruptcy documents.