Ulysses S. Grant
It truly is difficult to imagine a president going broke after leaving the White House, but that’s exactly what had happened to Civil War General Ulysses S. Grant.
He became a partner in financial firm Grant and Ward, but Ferdinand Ward embezzled investors’ money, leaving the firm and Grant bankrupt in 1884. Grant was receiving a military pension, but unfortunately it was not enough- since the president was suffering from throat cancer.
In order to have a stream of income come in, Grant had Mark Twain publish his memoirs, but he died before he could make any money from it.