8. Thomas Jefferson
Not all commander-in-chiefs have a good financial life. Although, Ulysses S. Grant and Abraham Lincoln went into Chapter 11 bankruptcy once in their prolific lives, while Thomas Jefferson faced the misfortune of filing for bankruptcy several times, as per a 2008 CNN article. He was infamous for being a squanderer, even after stepping down from his office. He extravagantly spent a lot of his income on million-dollar homes, which he was passionate about, along with expensive wine and good food.