Nathan Hale: The Spy Who Left No Intelligence

He is remembered as America's first great spy. As a young schoolteacher, he volunteered to go behind British lines, was captured, and faced the gallows with the famous words: “I only regret that I have but one life to lose for my country.” What the story almost never tells you is that Nathan Hale was a complete failure as a spy, and that his failure may have cost the young Americans New York City.

It was September 1776. Washington's army had just been routed at the Battle of Long Island and retreated to Manhattan. British General William Howe was pressing his advantage. Washington desperately needed intelligence like troop positions, landing plans, anything. He asked his officers for a volunteer to go behind enemy lines, and most declined. Nathan Hale, a twenty-one-year-old captain from Connecticut, stepped forward.

There was one problem. Hale had no experience in espionage. He had no story that would last through intense questioning. He had no contacts in British-occupied territory. His solution was to pose as a Dutch schoolmaster, which was a decent disguise except for one detail that multiple sources mentioned. Hale's face was badly scarred from gunpowder burns, making him immediately different and memorable to anyone he met.

His mission lasted roughly two weeks. He gathered sketches and notes, which he hid in the soles of his shoes. He was captured on September 21, 1776, attempting to return to American lines, and was probably betrayed by a Loyalist cousin who recognized him. He was brought before General Howe the same evening and hanged the following morning, September 22, with no trial and no chaplain present.

The intelligence he carried was never delivered. Washington received nothing from the mission. What is worse is that historians have noted that the timing of Hale's capture coincided with a series of fires that broke out in New York City, and some British accounts blamed the young spy for the destruction meaning his presence may have accelerated British security activity at a critical moment.

However, something amazing occurred in that orchard in Manhattan on the morning of his death. British witnesses reported that Hale died with unbelievable composure, calmly explaining his principles and expressing his regret in words that were stuck in the memory of all who listened. Captain Frederick Mackenzie of the Royal Welch Fusiliers wrote in his diary that Hale “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.”

He was a failed spy and a martyr. However, his courage in death inspired a generation of Americans to take risks many had refused. Sometimes the greatest intelligence an agent can provide is not information, but example.

Sources

Johnston, Henry P. Nathan Hale, 1776: Biography and Memorials. New Haven: Yale University Press, 1914.

Phelps, M. William. Nathan Hale: The Life and Death of America's First Spy. New York: Thomas Dunne Books, 2008.

Mackenzie, Frederick. Diary of Frederick Mackenzie. Cambridge: Harvard University Press, 1930.

Rose, Alexander. Washington's Spies: The Story of America's First Spy Ring. New York: Bantam Books, 2006.

Pennypacker, Morton. General Washington's Spies on Long Island and in New York. Brooklyn: Long Island Historical Society, 1939.