3) Theodore Roosevelt (Net worth: $125 million)

Theodore Roosevelt held the office of the president of the US between 1901 and 1909. He was born with a silver spoon in his mouth. He received a sizeable trust fund and more than 200 acres of land in Long Island. This 26th president of the US lost most of his fortune on a ranching venture in the Dakotas and had to work as an author to pay the bills.