Our First Martyred American Spy

Long before the days of the CIA and Cold War, even before the spies of the Civil War, our nation had a network of spies that rivaled any spy agency of today. The leader of this spy ring, the Culpeper Ring in New York City, was Benjamin Tallmadge, an officer in the Continental Army. One reason Tallmadge may have been so driven to create this spy ring is because his best friend from college, Nathan Hale, was hung as a spy on his first intelligence gathering mission in New York.

Nathan Hale was born in Connecticut in 1755. Before his fourteenth birthday, he and his brother, Enoch, were sent to Yale University to get an education. Nathan's father was a minister and planned for Nathan to follow in his footsteps.

At Yale, Nathan became close friends with Benjamin Tallmadge and William Hull, a man who worked with Tallmadge. Hale's university days created in him a desire to be free from the rule of the British Crown as it did with most of his contemporaries. When he graduated, instead of becoming a minister, he took a job teaching at a private school in East Haddam.

When war broke out, Hale was reluctant to join the army, but at the urging of Tallmadge in a letter, joined up in 1775. For the next year, he saw no action. It disturbed him because he felt he was doing nothing to further the independence of the American Colonies.

In September, Washington was desperate for intelligence about the British troop movements in Manhattan. That information would determine his next move. He asked for volunteers. At that time, most didn't consider spying a respectable occupation, and nobody was willing to volunteer for such a dangerous mission. Nathan Hale, who was eager to do something to help his country, stepped up and said he would do it.

Hale snuck into Manhattan and got the information he needed. Before heading back, he stopped at a tavern where he was recognized by Robert Rogers, commander of Rogers' Rangers. Earlier, Rogers had attempted to get free passage behind enemy lines, telling Washington he was a patriot. His real intentions were to spy for the British. Washington denied his request, but during that time, he had seen Hale in uniform.

Rogers needed proof Hale was a spy and invited him to his home where he informed Hale that he was a patriot. Hale fell into the trap, and was arrested. After admitting he was a spy, he was sentenced to hang by General William Howe.

When Hale was at the gallows, the last sight he probably saw was New York City burning. A fire had started accidently, but knowing it would help the Americans, many patriot civilians started more fires or did things to slow the British in putting out the fires. Many of these patriots were captured and executed. The fire did stop the British from taking up residence in the city.

Hale's last words were immortalized as the sentiment of American Patriots. "I only regret that I have but one life to lose for my country." This quote is reported by Tallmadge and Hull, Hale's friends who were not present at the execution. The quote is probably a condensed quote of what he really said. Hull and Tallmadge were at the site shortly after the execution to facilitate a prisoner exchange and talked to a British officer, John Montresor about what Hale's last words were. Others reported other things Hale may have said, so his speech was longer than the reported quote.

Frederick MacKensie, a British officer, wrote this diary entry for the day, "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."

Whatever the case, at his death, Hale was a patriot and the first American spy executed for his exploits of bravery.

Colonial Schooling

For many parents, the moment that their child goes off on that first day of school can be heartbreaking. It’s a realization that their child is slowly stepping out into the world—and away from home. Eventually, perhaps, for good.

This life-changing event is described with poignancy in the autobiography of renowned author and politician, William Allen White. (As quoted by Eric Sloane in The Little Red Schoolhouse):
“Ma was in the doorway,” he wrote, “and I left her full of tears, for she knew, having taught school, that I would never come back her baby. She knew that I was gone out of her life as a child and would return that noon a middle-aged person, out in the world for good and all.”

That was in the 1870’s. But not much has changed today. No doubt, many parents today feel as William White’s mother felt so long ago.


Bu this American tradition of going to school began early. In 1647, the colony of Massachusetts passed the Old Deluder Satan Act, requiring any town with 50 or more households to hire a teacher for reading and writing. If there were 100 households, that upped the requirement to operating a grammar school for older students. This law was passed because parents became lax in teaching the basics of reading and writing, and the concern was that the colonists be able to read their Bibles. Hence the name of the law, so “that old deluder, Satan,” could not “keep men from the knowledge of the Scriptures.”

While schools today fight to keep Christianity out of the curriculum, the education of young colonials was filled with prayers and the Bible. The usual tablet for teaching was called a hornbook, a wooden paddle with a parchment inscribed with upper and lower case letters as well as the Lord’s Prayer. The written document was affixed to the wood with a thin layer of processed cow’s horn—the colonial version of lamination.


Some youngsters began their schooling in a “Dame School” which was held in someone’s home where the children learned the basics of reading by the woman of the household. These dame schools were often the sole education for young girls.

If there was a schoolhouse in the community, it was one room and the schoolmaster that was hired was usually a young, unmarried man, who took the job before settling on a trade. Boys went to school in the winter for several weeks when there were no crops to tend. Girls (if they were lucky) went to school in the summer.

New England schools were numerous and paid for by local taxes. Farther west and south, these one-room places of learning became more scarce. The two colonies with the greatest numbers of formal schools were Virginia and Massachusetts—the first two colonies founded on American soil.

One of the more famous schoolmasters in colonial Connecticut started out teaching in the small community of East Haddam in the winter of 1773-74. The eighteen-year-old Yale grad was described as handsome, athletic and kind. Author Eric Sloan wrote that this teacher was so well liked that his students gave him a send-off party when he took a position in the larger town of New London.

“I’ll miss you,” the departing teacher said. “And I wish that part of me could stay back in East Haddam with you. I do regret there is only one of me.”

As this schoolmaster headed for his new teaching position, the rumbles of the Revolution were being felt. He joined the Continental Army while still a teacher in New London. But his other profession was as an American spy. When the British discovered secret military plans written in Latin and Greek and hidden in his shoe, Nathan Hale was arrested and then hung.

His famous last words embodied the spirit of the Patriot cause: “I only regret that I have but one life to lose for my country.”

Nathan Hale, beloved schoolmaster, was hung on September 22, 1776.


His schoolhouse in East Haddam is now a museum overlooking the Connecticut River.