10. Kenny Anderson

-cash blown: $60 million

Kenny Anderson earned around sixty million dollars during his NBA career. He married three times. Unfortunately the divorce with his first wife cost him a lot of money. Tami Akbar challenged Kenny into a prenuptial agreement that made her go with half his assets and eight thousand five hundred dollars monthly child support.

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She went further and celebrated her victory and custom made a license plate that stated ‘HIS CASH’. He was also supporting his six other children from the two other ex-wives and making payments on a house for his mother. He filed for bankruptcy claiming he had 41,000 dollars monthly expense to pay.