John Brown of Pittsfield Colonel John Brown ( October 19 , 1744 – October 19 , 1780 ) , often known as John Brown of Pittsfield because of his common name , was a Patriot , spy , soldier , and military leader , in the American Revolutionary War . He played a significant role as a courier between the Thirteen Colonies and Province of Quebec prior to the outbreak of the war , and then participated in military actions in Quebec and the frontiers of New York , where was killed in action on his 36 birthday . According to historian Christopher Ward , " Brown was one of those remarkable characters that one finds hidden in the crannies of history , almost unknown even to historians . " Life . Born to Daniel Brown in Sandisfield , Berkshire County , Massachusetts , he graduated from Yale University in 1771 , where he first met Benedict Arnold . He was a close friend to a classmate , David Humphreys , who also went on to serve in the Continental Army . In March 1775 , as a member of the Massachusetts Committee of Correspondence , he was sent to Montreal to begin communications with citizens there interested in taking up the Patriot cause . Meeting in April with Thomas Walker and other leading British - American merchants in Montreal unhappy with the British government and the terms of the Quebec Act , he was ultimately met with supportive inaction . He and his brother Jacob went on to serve with Benedict Arnold during the war , participating in the important capture of Fort Ticonderoga in May 1775 . In July , General Philip Schuyler sent him back to Montreal for a report on the military situation there . In August he returned , reporting that the British had only 300 soldiers at Fort Saint - Jean , but were improving its fortifications and building boats . In mid - August he again went north to meet with James Livingston , a Patriot sympathizer near Chambly . On August 25 , General Richard Montgomery received a letter from him indicating that the British had two war vessels nearly ready for launching on Lake Champlain . Following receipt of this letter , Montgomery launched the invasion of Quebec . Brown went on the serve under Montgomery and his successors in that campaign . On September 17 , 1775 Brown with 80 men opened action north of Fort St John but was driven back by 200 British and Canadians but not before he destroyed a key bridge and captured supplies en route to the Fort . He met with Ethan Allen at Longueuil on September 23 , where they hatched a plan to capture Montreal . For reasons unknown , Brown failed to hold up his part of the plan , and Allen was later captured in the Battle of Longue - Pointe . While serving under Montgomery , he was instrumental in warning Montgomery of low troop morale and the possibility of mutiny during the siege of Fort Saint - Jean . On October 18 , 1775 , Brown joined with James Livingston , 50 Americans , and 300 Canadians , to lay siege and capture the British fort at Chambly . This precipitated the end of the siege at Saint - Jean , and opened the route to Montreal . Brown and his troops crossed to the north shore of the St . Lawrence , isolating Montreal from Quebec City . In action during the Battle of Quebec , Brown and Livingston were responsible for diversionary tactics intended to distract the British defenders of the city . These tactics failed , and the attack ended in disaster , with Montgomery killed and Benedict Arnold wounded . He was killed in action on his 36th birthday near the ruins of Fort Keyser in Stone Arabia , NY , on the Mohawk Valley frontier .