6. Ulysses S. Grant (1869-1877)
His brief, illustrious career as our nation’s highest-ranking general notwithstanding, Grant never earned a great deal of money and often lived well beyond his means. This was especially the case after his presidency, when he and his wife traveled the world, dining with foreign dignitaries and staying in expensive hotels. In 1881, Grant’s son, Buck, convinced his father to enter an investment partnership with an associate of his, Ferdinand Ward, for $100,000. Ward mismanaged and embezzled Grant’s assets, and when the firm of Ward and Grant went bankrupt, the former was sent to prison, and Grant was left with hundreds of thousands in debt. He went bankrupt, and was only able to save his family further financial hardships by selling his civil war memoirs for nearly half a million dollars – published shortly after his death.