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When that crisis began to subside, Captain Montgomery returned to England where he became associated with several Whigs who were friendly to the Americans and began to have doubts about British treatment of the colonists. In 1771, Montgomery sold his army commission for £1500 pounds and moved to America, intending to become a farmer.
Montgomery purchased a farm at King's Bridge north of New York City and soon married Janet Livingston, whom he had met during his earlier travels. She was part of the powerful Livingston political dynasty that included Philip Livingston, who signed the Declaration of Independence and William Livingston who signed the US Constitution and later notables such both Presidents Bush, Eleanor Roosevelt and actress Jane Wyatt.
Due to his political ties with the Livingston family, Richard was elected to the New York Provincial Congress in 1775 where he was asked to help prepare the defenses of New York and organize its militia. Soon after, he was appointed a brigadier general in the Continental Army. Shortly afterwards, George Washington announced plans to invade Canada. General Philip Schuyler, who was the senior general, became ill shortly before the invasion and Montgomery took charge in his place. Montgomery captured Fort St. Jean and marched without opposition into Montreal, capturing the first British regimental flag of the war in the process, for which he received a commendation from George Washington.
Unaware that he had received a promotion to Major General on December 9th, Montgomery marched on to Quebec where he joined the forces of Colonel Benedict Arnold who had just traipsed across the wilderness of Maine to join him. Montgomery continued the Siege of Quebec for several weeks with little success. On the morning of December 31st, 1775, General Montgomery led a courageous assault on the city and was killed by grapeshot from defending Canadian militia.
General Richard Montgomery was buried in Quebec on January 4, 1776. His remains were moved to St. Paul's Chapel on Manhattan Island in 1818. He is considered one of the first heroes of the American Revolution.
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