dorky
Tompkins was baptized Daniel Tompkins, but added the middle initial "D." while a student at Columbia College to distinguish himself from another Daniel Tompkins there. I haven't found a source to say what the middle initial stood for. A Wikipedia article thinks it might be for "Decius" but there's no source for that. Tompkins was born in Scarsdale, Westchester County, New York at the estate of Fox Meadow. He graduated from Columbia College in New York City in 1795. Tompkins studied law and in 1797 was admitted to the New York State bar, practicing in New York City. He went on to become a distinguished jurist. On February 20, 1798, Tompkins, then a 23-year-old lawyer, married 16 year old Hannah Minthorne. They had eight children together
Tompkins was selected to be a delegate to the New York State Constitutional Convention in 1801. He was elected as a member of the New York State Assembly in 1804, and was elected to the 9th United States Congress, but resigned before the beginning of the term. He decided instead to accept an appointment as associate justice of the New York Supreme Court. Only 30 when appointed, he served from 1804 to 1807.
On April 30, 1807, Tompkins ran for Governor of New York and defeated incumbent Governor Morgan Lewis by over 4000 votes. He held that office until 1817, winning re-election in 1810, 1813 and in 1816. During the War of 1812, Tompkins was an effective war governor. He helped to reorganize the state militia and supported the formation of a standing state military force. He turned down an appointment as United States Secretary of State by President James Madison in 1814. In 1815 Tompkins established a settlement along the eastern shore of Staten Island that came to be called Tompkinsville. In 1817 he began operating a daily steam ferry service between Staten Island and Manhattan. That same year he suggested that July 4, 1827, be set as the date on which all slaves in New York state should be freed.
While Governor of New York, Tompkins personally borrowed money with his own property as collateral when the New York state legislature would not approve the necessary funds for the War of 1812. After the war, neither the state nor the Federal government reimbursed him so he could repay his loans. Years of litigation did not end until 1824, at which point the State of New York and the Federal government owed Tompkins $90,000. His political nemesis Dewitt Clinton obstructed the repayment, causing financial hardship for Tompkins, a factor in his subsequent heavy drinking. It seems like Clinton was being mean-spirited and petty. Another theory is that Tompkins exaggerated his loan and was accused of embezzlement. His reputation suffered from the whole business.
Tompkins was elected Vice President on the ticket with James Monroe in 1816, and was reelected in 1820, serving from March 4, 1817, to March 4, 1825. In 1820, while serving as Vice President, he ran for Governor of New York against incumbent DeWitt Clinton. The election was held in April 1820 and Tompkins lost.
Tompkins' financial problems took a toll on his health. He became an alcoholic and at times, when serving as Vice President, he presided over the Senate while intoxicated. Fellow New Yorker and future Vice-President and President Martin Van Buren called Tompkins "the most injured of men." Another politician called said that Tompkins had "degenerated into a degraded sot." Finally in 1822 he just stopped coming to the Capitol altogether.
Tomkins died in Tompkinsville on June 11, 1825, 99 days after his term as Vice President ended. He had the shortest retirement of any Vice-President who survived the office. He was interred in the Minthorne vault in the west yard of St. Mark's Church in-the-Bowery, New York City.
Tompkins was the last Vice President to be elected to two terms with the same President until Thomas R. Marshall (with Woodrow Wilson in 1912 and 1916.)