The First Patriot Spy?

Nathan Hale

Earlier this week was the 236th anniversary of the death of Nathan Hale. Hale is a peripheral but key figure in the first two books of the Yankee Doodle Spies Series.

On 22d September 1776, Nathan Hale, the first American (not rebel) spy was hanged by the British.  Born in 1755 on a farm near Coventry, Connecticut,  Hale attended Yale and after graduation in 1773, became a schoolmaster. Caught up in the fervor of patriotism that swept the colonies after the battles of Lexington and Concord, he joined the Continental Army forming around Boston in 1775. At first ambivalent, Hale joined the Cause after receiving a letter imploring him to service from his close friend, Benjamin Tallmadge. Ironically, (or causally) Tallmadge later became head of Washington's intelligence unit (and a recurring character in Yankee Doodle Spies).

Hale rose to the rank of Captain in a Connecticut Regiment but later joined Lieutenant Colonel Thomas Knowlton's (also a peripheral figure in the series) elite Ranger battalion. Hale was by all accounts an extremely handsome man, tall for his day, and extremely well-spoken. Liked by all, his commander, Knowlton, held him in special regard.  After the Continental Army retreated from its disastrous defense of Long Island, Lieutenant General George Washington needed to know the strength, activities, and morale of its British occupiers. Washington was most concerned with the time and place of the inevitable British assault on the Island of New York (now called Manhattan). He asked Knowlton to provide an agent for this extremely high-risk mission. In a society obsessed with the idea of "honor", espionage was an even dirtier business than it is today. Because of that, none of the officers in Knowlton's unit would volunteer. But Hale, who had yet to see combat and was bored with the so-far administrative nature of his duties. So he offered his services.

Spying under spurious cover?

In a mission both bold and futile, he was launched onto Long Island via Connecticut by longboat under the cover of an itinerant schoolmaster. In a lesson in trade-craft,  the idea of a young schoolmaster traveling a war zone seems desperate, if not ridiculous. However, Hale was a schoolmaster. It is always easiest to portray something close to what you are, have experienced, or know. Just how he was captured is subject to much speculation. In his book, Washington's Spies, author Alexander Rose claims the famous Loyalist Ranger Robert Roberts caught him.  Roberts was an American hero during the French and Indian War but sold his services to the crown for a commission during the American Revolution. According to Rose, Roberts and his operatives identified Hale on Long Island and lured him into a trap. Other accounts differ. Regardless, the cover did not hold up.

A Spy Uncovered

What we do know for certain is that Hale was captured on the 21st of September and was immediately brought for questioning before the British commander, General William Howe. By then, The British Army had already invaded New York. Howe had just moved into the Beekman Mansion (near the present corner of 51st Street and 1st Avenue on Manhattan). Intelligence information was found on Hale's person and since this was not in code or invisible ink, he was totally compromised.

The next morning, a Sunday, the erstwhile spy was marched north, about a mile up the post road to the Park of Artillery located next to a public house called the Dove Tavern, about 5 1/2 miles from the city limits. There, he was hanged.  Hale's apocryphal quote prior to execution is somewhat controversial and there are several accounts of it from various sources, all plausible. Hanging was considered a death for thieves and murderers, not soldiers, and certainly not an officer. It is likely  Hale meant his last words as much to remove the dishonor of being a spy, as much as providing a model of patriotic self-sacrifice.

I have but one duty...

To me, the most credible statement allegedly made by Nathan Hale prior to his execution comes from in the diary of a British officer named Lt. Robert MacKensie, who served in New York at the time. The entry is particularly plausible because it was made on the very day of Hale's execution.

"...He behaved with great composure and resolution, saying he thought it the duty of every good Officer, to obey any orders given him by his Commander-in-Chief; and desired the Spectators to be at all times prepared to meet death in whatever shape it might appear."