Highest Office Held: President of the United States
President Grant decided to take two years to travel the world after leaving office. The problem? He couldn't afford it.
He had little cash left after he returned, and immediately proceeded to make matters worse with a botched run for a third term, the establishment of the fast-failing Mexican Southern Railroad, and the formation of an investment banking business with a man who would ultimately fleece Grant of his remaining cash.
After this string of missteps, he still felt honor-bound to repay a debt to William H. Vanderbilt, whom he owed $100,000. He paid him back by selling his souvenirs from the Civil War. One thing you can say for Grant is that all of this financial idiocy led to the creation of insane memoirs, which ultimately made a lot of other people, including Mark Twain, a lot of money after his death.