Harry Truman
Harry Truman was a serial entrepreneur who racked up a mountain of debt after investing in a zinc company that failed and opening a men’s furnishings shop that went bust.
He was still deep in debt when he entered the White House. Truman refused to declare bankruptcy on moral grounds, but he couldn’t meet his payment obligations on his presidential salary of $75,000.
In response, Congress raised the president’s pay to $100,000 in 1949. (Today, it’s $400,000.) But Truman struggled again after he left office, when he tried to get by on just an Army pension of $112.56 a month.