21 Bankrupt Celebrities – They Had It All And Spent Even More

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9. Donald Trump

He filed for bankruptcy, believe it or not, four times in his life: 1991, 1992, 2004, and 2009. He inherited his entire fortune from his father and managed to wreck it four times over. What an able businessman. We just don’t like this guy.

Trump recently said that filing for bankruptcy is not unusual for big businesses and that they do it all the time. Did any of them file for Chapter 11 four times, as Trump did? We don’t think so. However, it’s important to mention that Trump never personally went bankrupt. He’s too sly and clever for that. His businesses however, did suffer, but he makes it seem it was almost on purpose.

His first bankruptcy was in 1991 when he was forced to sell his personal airline, a yacht and a half his ownership at Trump Taj Mahal in Atlantic City. His other bankruptcies all involved his AC casinos and resorts.

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