William McKinley
McKinley’s troubles began when he co-signed on a loan for a friend. The friend defaulted on the loan and went bankrupt, and McKinley was not long behind.
He was in office as governor of Ohio when he declared bankruptcy in 1893. Yet just three years later, he was elected president.
Despite his fairly well-publicized money troubles, McKinley won the election by promising to restore the economy and create a gold standard to stabilize the dollar.