Early Life; Service During The War of 1812
Gregory was born in Norwalk, Connecticut. While in the American merchant marine, he was impressed by the British in an incident typical of those which led in part to the War of 1812. After escaping, Gregory was appointed a midshipman on January 16, 1809, by President Jefferson and reported to the Revenge, commanded by Oliver Hazard Perry.
In March, 1809, Gregory was transferred to the Gulf Squadron at New Orleans, Louisiana. In 1811, while serving in the Vesuvius and as acting captain of Gun Boat 162, Gregory participated in three notable actions. On August 7, off Pensacola, Midshipman Gregory attacked and crippled the pirate schooner La Franchise. On August 10, off Mobile, he attached and captured the pirate schooner Santa Maria. On September 11, between Brassa and Barataria, Louisiana, midshipman Gregory and his crew captured the pirate ship La Divina, and the schooners La Sophie and Le Vengeance.
During the War of 1812, he served on Lake Ontario under Commodore Isaac Chauncey and participated in attacks on Toronto, Kingston, and Fort George. In August, 1814, Gregory was captured by the British; refused parole, he was sent to England and remained there until June, 1815, months after the end of hostilities.
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