Harry S. Truman
The 33rd president spent most of his life in financial turmoil. He had a modest upbringing, and years of bad investments, including a men's clothing store and a mining and oil company, kept him in debt. However, he never filed for bankruptcy. After his presidency, Truman and his wife Bess moved into his mother-in-law's home in Independence, Mo. Truman was one of the first presidents to receive a pension, a sum of $25,000 annually, which helped to keep him afloat. He and his wife were also the first recipients of Medicare after it was signed into law.