On September 22, 1776, Nathan Hale, a captain in the 19th Regiment of the Continental Army, was hanged by the British in Manhattan, near the artillery park at what is now 66th Street and Third Avenue. He was 21. Under the law of war, spies were hanged, and the British had just taken the city and had no reason to be lenient.
The mission had begun a week earlier. Washington's army had been driven out of Brooklyn on August 27 with about 2,000 casualties, and had been forced off Manhattan at Kip's Bay on September 15. Washington had lost the city and did not know what the British intended next. When he asked for a volunteer to go behind British lines and find out, Hale, whose regiment was at Harlem Heights, accepted.
He was a schoolmaster. Hale had graduated from Yale in 1773, taught at East Haddam and New London, and joined the Connecticut militia in 1775. He had been in the siege of Boston. He crossed to Long Island on September 12 in civilian clothes, with a Yale classmate's Latin school diploma in his pocket as a cover, and spent about a week sketching fortifications and asking questions. He was arrested on September 21, probably at a tavern in Flushing, and the drawings were found in his shoes.
The British treated him well and then hanged him. General Howe's provost marshal, William Cunningham, is usually named as the man who supervised it and who refused him a bible and a clergyman. The famous line, I only regret that I have but one life to lose for my country, comes from John Montresor, a British engineer officer who spoke with Hale the night before and repeated it to an American officer at a truce the next day. It is not corroborated, and it sounds like it was polished on the way.
He was not the first American spy to die, and the Continental Army ran agents in New York throughout the war, most of them more usefully. What made Hale the emblem was the age, the volunteering, and the sentence. He has no known grave. A statue stands outside the Connecticut state capitol, and there is another at Yale, and one at the CIA headquarters in Langley.