Nathan Hale - Wikipedia

On September 10, 1776, George Washington asked for a spy volunteer; Nathan Hale volunteered. From the article:

"Nathan Hale was born in Coventry, Connecticut, in 1755 to Richard Hale and Elizabeth Strong. In 1769, when he was fourteen years old, he was sent with his brother Enoch, who was sixteen, to Yale College. Nathan was a classmate of fellow patriot spy Benjamin Tallmadge.[2] The Hale brothers belonged to the Linonian Society of Yale, which debated topics in astronomy, mathematics, literature, and the ethics of slavery. Nathan graduated with first-class honors in 1773 at age 18 and became a teacher, first in East Haddam and later in New London.[3]

After the Revolutionary War began in 1775, he joined a Connecticut militia and was elected first lieutenant within five months.[4] His militia unit participated in the Siege of Boston, but Hale remained behind. It has been suggested that he was unsure as to whether he wanted to fight, or whether he was hindered because his teaching contract in New London did not expire until several months later, in July 1775. On July 4, 1775, Hale received a letter from his classmate and friend Benjamin Tallmadge, who had gone to Boston to see the siege for himself. He wrote to Hale, "Was I in your condition, I think the more extensive service would be my choice. Our holy Religion, the honor of our God, a glorious country, & a happy constitution is what we have to defend."[5] Tallmadge's letter was so inspiring that, several days later, Hale accepted a commission as first lieutenant in the 7th Connecticut Regiment under Colonel Charles Webb of Stamford.

In the following spring, the army moved to Manhattan Island to prevent the British from taking over New York City. In September, General Washington was desperate to determine the location of the imminent British invasion of Manhattan Island. To that end, Washington needed a spy behind enemy lines, and Hale was the only volunteer.[3]
Intelligence-gathering mission
The Battle of Long Island led to British victory and the capture of New York City via a flanking move from Staten Island across Long Island. Hale volunteered on September 8, 1776, to go behind enemy lines and report on British troop movements. He was ferried across on September 12. It was an act of spying that was immediately punishable by death and posed a great risk to Hale.

During his mission, New York City (then the area at the southern tip of Manhattan around Wall Street) fell to British forces on September 15 and Washington was forced to retreat to the island's north in Harlem Heights (what is now Morningside Heights).[6] On September 21, a quarter of the lower portion of Manhattan burned in the Great New York Fire of 1776. The fire was later widely thought to have been started by American saboteurs to keep the city from falling into British hands,[7] though Washington and the Congress had already denied this idea. It has also been speculated that the fire was the work of British soldiers acting without orders. In the fire's aftermath, more than 200 American partisans were rounded up by the British.

An account of Nathan Hale's capture was written by Consider Tiffany, a Connecticut shopkeeper and Loyalist, and obtained by the Library of Congress. In Tiffany's account, Major Robert Rogers of the Queen's Rangers saw Hale in a tavern and recognized him despite his disguise. After luring Hale into betraying himself by pretending to be a patriot himself, Rogers and his Rangers apprehended Hale near Flushing Bay in Queens, New York.[8] Another story was that his Loyalist cousin, Samuel Hale, was the one who revealed his true identity.

British General William Howe had established his headquarters in the Beekman House in a then rural part of Manhattan, on a rise between what are now 50th and 51st Streets between First and Second Avenues,[9] near where Beekman Place commemorates the connection. Hale reportedly was questioned by Howe, and physical evidence was found on him. Rogers provided information about the case. According to tradition, Hale spent the night in a greenhouse at the mansion. He requested a Bible; his request was denied. Sometime later, he requested a clergyman. Again, the request was denied.

According to the standards of the time, spies were hanged as illegal combatants. On the morning of September 22, 1776, Hale was marched along Post Road to the Park of Artillery, which was next to a public house called the Dove Tavern (at modern-day 66th Street and Third Avenue), and hanged.[10] He was 21 years old. Bill Richmond, a 13-year-old former slave and Loyalist who later became a boxer in Europe, was reportedly one of the hangmen, responsible for securing the rope to a strong tree and preparing the noose."