Highest Office Held: President of the United States
Thomas Jefferson's beautiful home, Monticello, ranks as one of history's greatest man caves. While Jefferson spent most of his post-political life filling his home with books, wines, and art, he neglected to focus on getting his plantation to turn a profit.
Though he lived the high life nestled in his ornate study, most of his meticulously collected possessions were sold off after his death to satisfy the debts he mounted gathering all that shit in the first place. Jefferson wracked up a massive tab, totalling over a million dollars in today's money.