No.2: Donald Trump
Before his presidency, Donald Trump was known for flashy deals and big risks. Though he never declared personal bankruptcy, four of his companies—including casinos and hotels—filed for Chapter 11 between 1991 and 2009.
In the first case alone, Trump was personally liable for $832 million and even had to sell his yacht, The Trump Princess. Still, he used legal loopholes to shield his personal wealth, recover, and continue amassing billions. His bold tactics earned him celebrity status—and eventually the presidency.
