John F. Kennedy
Even before becoming our 35th president, John F. Kennedy was pretty set in the financial department. But despite his privileged upbringing and a trust fund worth about $170 million in today's dollars, the political playboy never carried cash and depended on his friends and even his secret service agents to pick up the tab wherever he went. Rumor has it he even clashed with Jackie over spending on clothes and groceries. Jeez.