Rudy Giuliani files for BANKRUPTCY and lists more than $500million in debts
(www.dailymail.co.uk)
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I'm not sure how much he's screwing the system, because filing bankruptcy is not going to save him from having to pay out on those defamation lawsuits.
From the article above:
It just bothers me that people are so giddy about someone being that fiscally retarded, and passing his debts onto others, just because they think it will prevent those people from collecting on their lawsuits. It won't.