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This Week in History: “I am the Yankee Doodle boy,” the story of Nathan Hale 

The University of Connecticut in Storrs is a place I like to call pretty darn close to the middle of nowhere. As a result, during my stay over the summer doing research, when I wasn’t in the lab, I often spent my time exploring the Connecticut countryside. Trekking through the abandoned “Factory Hollow” in what is now Gay City State Park was quite fun, but another interesting relic from the revolutionary days caught my eye — the soldier Nathan Hale.  

In fact, it would have been quite difficult for me not to see him. He is everywhere. In the surrounding areas of Bolton, Coventry and Mansfield Hollow, his statue appears along the road, his name on street signs and his very homestead is one I passed many times. So naturally, I had to find out, who is this guy? And his story might surprise you (especially if you haven’t grown up in the state of Connecticut’s education system). 

This week in history, Sept. 22, 1776, Nathaniel Hale of Coventry, Conn., the first spy of the Revolutionary War, was executed for espionage. Another interesting facet of this story was that, like many of the students currently attending UConn, he was just 21 years old.  

Statue of Nathan Hale, the first spy of the Revolutionary War, located in Connecticut. Photos courtesy of @flickr

Hale’s story begins like most white men in the 18th century; he grew up on a homestead with his brothers and sisters and learned how to fish, hunt and do chores to maintain the land. In 1769, he and his brother Enoch decided to pursue higher education at Yale University, which was just as much of a hot spot for political discourse as colleges are today. It was here that Hale first became interested in the Patriots’ cause. After graduating in 1773, Hale became a schoolteacher in New London, Conn., before eventually joining the Continental Army as a lieutenant in 1775 and being promoted to captain in 1776. It was then that, under Lieutenant Colonel Thomas Knowlton, he volunteered to cross enemy lines as a spy on Sept. 8 of that year. 

Now, a large part of why we know Hale’s story is because although he was a spy, he wasn’t a very good one. His friend Captain William Hull even encouraged him not to go, feeling that he was too open, often wearing his heart on his sleeve. But what Hale did excel at was illustrating fortified British encampments, which ultimately led him to pursue this role. 

For Hale, his mission was over before it even began when he caught the attention of British Army Major Robert Rogers. Before Hale’s arrival on Long Island, Rogers’ role was to rat out defectors from the British Army, among other undesirable things. To get an idea of who Hale was dealing with, Rogers was once described by one of his subordinates as, “subtil & deep as Hell itself… a low cunning cheating back biting villain.” Sounds like a nice guy, right?  

Statue of Nathan Hale, the first spy of the Revolutionary War, located in Connecticut. Photos courtesy of @flickr

Rogers had heard about Hale’s suspicious arrival on Long Island and was able to track him down by Sept. 19. He actually tracked Hale for hours without him noticing. He saw that Hale had been gathering information and jotting down notes on the British Army. The trap was set; the night before Hale was to leave, Rogers approached him while he dined, spouting lies about how he was a patriot trapped behind British lines. Hale, being the trusting and naive young man that he was, told Rogers that he was a spy. However, Rogers still needed more proof and witnesses, so he invited him to breakfast the next morning, to which Hale said yes. It was here that his future was done for. Believing that he ate with patriots, he continued to spout his secrets. Eventually, they captured him. Realizing that he had been bamboozled, Hale denied everything. Regardless, he eventually did admit to his deeds and was executed within the following days. 

Despite his unfortunate end, Hale’s legacy was quite successful. He has his own statue at the CIA, where they recognize him as the first American spy. Historian George Dudley Seymour even purchased the homestead in 1914 to maintain his role in our history books.  

Overall, when I think about Nathan Hale, I feel a mixture of pride and pity. Pride from my ingrained sense of American nationalism from watching “Hamilton,” and pity in the sense that he was really just a gullible young man who wanted to fight for what he thought was right. Whether Hale would fight for this country given the current state of affairs, that’s up for you to decide. 

Fun Fact: “Yankee Doodle” is the official state song of Connecticut. 

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