#33 Harry Truman
The 33rd president of the United States was near broke for the majority of his life. He came from a ordinary upbringing, but it was his terrible investments that really put him in debt. He invested in a men’s clothing store and mining company, which ultimately flopped. Even after his time in office, his wife and him moved in with their in-laws located in Missouri. In order to keep him going, he received a pension post-presidency of $25,000 and was the first recipient of Medicare.