He is, however, the great-grandson of William Windom (1827-1891), 33rd and 39th U.S. Secretary of the Treasury, first serving under Garfield and Arthur and later Benjamin Harrison, besides being a Representative and then Senator from Minnesota. Windom was regarded highly enough to earn a depiction on a series of $2 silver certificates issued after his death in office.
Windom also took a very modest stab at the presidency. In 1880, he received 10 votes on the first ballot at the Republican National Convention that year in Chicago as a favorite son candidate. The nomination ultimately went to the dark-horse James A. Garfield, who went on to the White House and an early grave.