Kenny Anderson

Downfall: Paying his friends to hang out with him.

If you’re looking for a lesson in how to make $60 million disappear than Kenny Anderson is the perfect teacher. The retired point guard paid his friends a $10,000 allowance to keep him company, filled up his eight-car garage with a bevy of expensive rides, lost $5.8 million in his divorce, plus paid child support for eight children.

On a positive note, Anderson recently received his college degree.

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