While still living in
New York, Gregory was elected a
justice of the peace. In 1856, he was candidate for the
United States House of Representatives from
New York's 19th congressional district, losing to
Oliver A. Morse. After moving to
Wisconsin, he served as mayor of Madison from 1873 to 1874. In 1870, he was again a candidate for the United States House of Representatives, this time from
Wisconsin's 2nd congressional district, in a
special election following the death of
Benjamin F. Hopkins. He would lose to
David Atwood. Gregory ran again from the same district in 1880, losing to incumbent
Lucien B. Caswell. He was a
Democrat. ==References==