13. Donald Trump: Yes, Mr. Moneybags really was pulling his pockets out at one point: the host of NBC’s The Apprentice has filed for bankruptcy on two occasions, though rebounded, as his estimated net worth had climbed to $2 billion as of 2010. 15. Gary Coleman: The diminutive Diff’rent Strokes star sure could have used Mr. Drummond’s help in 1999, when he filed for bankruptcy. The late child star, who played Arnold Drummond on the hit 80s comedy, said medical expenses and mismanagement were the reasons he was out of cash.
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