William Henry Harrison
William Henry Harrison spent much of his life getting deeper and deeper into a financial hole. After quitting medical school, getting married and having 10 children, Harrison decided to embark on a military career to cover the bills.
Building on his military success, Harrison was appointed the U.S. ambassador to Colombia and spent a year abroad —and his debt only got worse. When he returned home, his family farm had lost its crops to bad weather and was in trouble with creditors.
By the time he got to the White House, Harrison was close to insolvency. He served as president for only about a month before he became ill and died in 1841.