4. Donald Trump
Despite having filed for bankruptcy four times in total, Donald Trump still flaunts his dollars to this day. This is quite incredible. Occurring between 1991 and 2009, Trump’s four bankruptcies would certainly have put him in the poor house, right? However, this is not the case. With some intelligent accounting, Trump filed for a corporate bankruptcy, rather than personal. This protected his personal assets and allowed him to keep spending, while providing bail to his company on multiple occasions.