Daniel D. Tompkins

Born in Scarsdale in 1774, Tompkins practiced law in New York City after Columbia, sat on the state's highest court, then beat the incumbent to become governor in 1807. He held the office through the entire War of 1812, often reaching into his own pocket to equip and pay militia when the legislature wouldn't. That generosity wrecked him: by war's end his finances were in tatters. He rode the Democratic-Republican ticket with James Monroe to the vice presidency in 1816 and served two full terms — the only nineteenth-century VP to do so — but the debt and the strain never lifted. He tried for go…