The First Patriot Spy?

Nathan Hale

Earlier this week marked the 236th anniversary of Nathan Hale's death. Hale is a minor yet significant figure in the first two books of the Yankee Doodle Spies Series.

On September 22, 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 graduating in 1773, became a schoolteacher. Caught up in the patriotism sweeping the colonies after the battles of Lexington and Concord, he joined the Continental Army forming around Boston in 1775. Initially ambivalent, Hale decided to join the Cause after receiving a letter from his close friend, Benjamin Tallmadge, urging him to serve. Ironically, or perhaps causally, Tallmadge later became the 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 era—and very well-spoken. Liked by everyone, 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 assess the strength, activities, and morale of the British occupiers. Washington was especially concerned about the timing and location of the inevitable British assault on the Island of New York (now called Manhattan). He asked Knowlton to provide an agent for this very high-risk mission. In a society obsessed with "honor," espionage was considered even dirtier than it is today. Because of that, none of the officers in Knowlton's unit volunteered. But Hale, who had yet to see combat and was bored with the administrative duties he had so far, offered his services.

Spying under spurious cover?

In a mission both daring and futile, he was clandestinely transported onto Long Island from Connecticut by longboat, disguised as an itinerant schoolmaster. In a lesson in tradecraft, the idea of a young schoolmaster traveling through a war zone seems desperate, if not downright absurd. However, Hale was indeed a schoolmaster, and it’s always easier to depict something similar to your own experience or background. The exact details of his capture are a matter of much debate. In his book, *Washington's Spies*, author Alexander Rose states that the renowned Loyalist Ranger Robert Roberts captured him. Roberts was a hero during the French and Indian War but switched allegiances and sold his services to the British during the American Revolution. According to Rose, Roberts and his men identified Hale on Long Island and lured him into a trap. Other accounts tell a different story. Regardless, the cover was blown.

A Spy Uncovered

What we do know for sure is that Hale was captured on September 21 and immediately brought in for questioning by 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 current corner of 51st Street and 1st Avenue in Manhattan. Intelligence found on Hale, which was not in code or invisible ink, meant he was completely compromised.

The next morning, a Sunday, the former spy was marched north about a mile along the post road to the Park of Artillery, located next to a pub called the Dove Tavern, roughly 5 1/2 miles from the city limits. There, he was hanged. Hale's supposed quote before execution is somewhat debated, and several different accounts exist from various sources, all of which seem plausible. Traditionally, hanging was reserved for thieves and murderers, not soldiers, especially not officers. It’s likely Hale intended his last words to both dispel the dishonor of being labeled a spy and to serve as a model of patriotic sacrifice.

I have but one duty...

To me, the most credible statement reportedly made by Nathan Hale before his execution comes from the diary of a British officer named Lt. Robert MacKensie, who was serving in New York at the time. The entry is especially believable because it was written 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."