Captain Nathan Hale, Patriotic Soldier, Spy and Hero of the State of Connecticut

245 years ago, on September 22, 1776, Captain Nathan Hale was hanged as a spy by the British in New York. There are several mysteries and little-known facts surrounding Hale’s service and his execution that I cover in this short article.

Nathan Hale was a classmate and friend of Benjamin Tallmadge at Yale, both graduating from the class of 1773. Tallmadge would later serve as a cavalry officer as well as the officer in charge of the famous Culper Spy Ring during the American Revolution. The purpose of this ring was to collect information on the status of British, Loyalist and Hessian units in New York and their various plans to undertake expeditions from British headquarters in New York.

Before the Culper Ring, one of the first Patriot spies to attempt to gather information on the British in Manhattan was Hale. What many readers may not know is that Hale was a post-Yale schoolteacher, first in the countryside of East Haddam, then in downtown New London. His surviving letters indicate that he was much happier as a young bachelor living in New London. Many will also be surprised to know that he and Tallmadge (who taught at Wethersfield) broke traditional barriers by teaching girls in elementary school, offering classes separate from their male peers.

Another overlooked fact about Hale is that he served in the Continental Army before embarking on his famous and fateful spy mission. In fact, after being appointed lieutenant in Colonel Charles Webb’s 7th Connecticut Regiment, Hale was later promoted to captain of the Knowlton Rangers. This elite Connecticut unit was commanded by Colonel Thomas Knowlton. Because it was a ranger-style unit that performed certain military intelligence functions, the U.S. Army Intelligence dates its founding to 1776, as shown on their seal.

Hale was the only patriot willing to volunteer at General George Washington’s request for a spy to infiltrate behind enemy British lines in the city to gather information. This was largely because espionage was considered a non-gentleman to a soldier at the time. Tragically, Hale had no real training or prior experience with espionage. He didn’t have a lot of blanket either. He pretended to be a schoolteacher looking for a job, taking his Yale degree with him.

Statue of Nathan Hale.

After a whaling crossing from Norwalk to the north shore of Long Island, a much more experienced warrior caught Hale on Long Island. Major Robert Rogers of the Queens Rangers was already known to have led his famous Rogers’ Rangers in the previous French and Indian War. Rogers caught Hale in a pub, convincing Hale to divulge his true identity, his patriotic feelings, and his spy mission. Rogers had the pub surrounded by his rangers. After his arrest he was convicted of espionage by British General William Howe. He was sentenced to be hanged as a spy. Unfortunately, the British did not allow him to use a Bible or a pastor when hanging him, and they also tore up his last letter he wrote to his parents.

It is not known exactly where he was hanged and then buried in an unmarked grave, but the most likely location was near a plaque in Hale towards the upper east side. A British officer’s diary indicated that Hale’s hanging had taken place at the “Royal Artillery Park near the Dove Tavern in Old Post Road”. This road is now 3rd Avenue and the plaque is on the exterior wall of a building at 1110 3rd Avenue. Hale never married and had no children. The Hale family then erected a large cenotaph (a memorial with an empty grave) in their hometown of Coventry, Connecticut.

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