$125 million In office:
1901 to 1909 26th president
Born to a prominent and wealthy family, Roosevelt received a sizable trust fund. He lost most of his money on a ranching venture in the Dakotas and had to work as an author to pay bills. Roosevelt spent most of his adult years in public service. His 235-acre estate, Sagamore Hill, now sits on some of the most valuable real estate on Long Island.
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