Painting by Don Troiani,

New York was critical piece in the puzzle of the colonial war effort since its deep harbors and the lifeline of the Hudson River made the area a strategic powerhouse for the side who captured it. If the British could gain control of New York, they would have free course into the heart of the continent.

Although Washington’s nearby army was some 20,000 strong, the men – and boys – were ill-equipped to withstand another harsh New England winter. Up to this point, Washington had been relying on information gathered by couriers and other informal means of intelligence. Now, he needed something more – a spy.

Spying was not an unknown art in war, but during the American Revolution, it was one with ignominious associations as the worst of wartime criminal activity. If a spy was caught, there would be no honorable death – he was destined only for the hangman’s noose.

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Though there was no official organization for the training of spies, Thomas Knowlton, a lieutenant colonel in the American army handpicked promising recruits for an elite force of soldiers called “The Rangers.” Nathan Hale, a young school-teacher turned soldier was one such Ranger.

When Knowlton laid down General Washington’s proposition – that one of the Rangers should act as a spy – none spoke up. To be caught was surely a death sentence.

But Hale saw this mission an opportunity to fulfill his duty. His fellow Rangers tried to dissuade him. Some said he was too handsome for such a job; a memorable face like his would stick out in a crowd. Others thought Hale’s “nature was too frank and open to [practice] deceit and disguise.”

Hale, however, would not waver. He believed it was God’s will to serve his country, even if it meant his own, personal humiliation. Hale told his friends,

I think I owe to my country … the accomplishment of an object so important, and so much desired by the commander of her armies – and I know of no other mode of obtaining the information, than by assuming a disguise and passing into the enemy’s camp … every kind of service necessary for the public good becomes honorable by being necessary.

Late one September evening, Hale left his uniform and personal effects with a fellow soldier and went alone, on foot, across the British lines. He was armed with nothing but the garb of a Dutch schoolmaster and his Yale diploma. Posing as a teacher looking for work, Hale was to gather intelligence about the British position and return to General Washington in time to formulate a response plan for the American army. New York was swarming with British troops – a contingent of approximately 30,000 British soldiers and Hessian mercenaries waited, on shore and in ships, for British General Howe’s order to take New York.

Little is known of Hale’s movements while he was behind enemy lines. What we do know is that he successfully gathered intelligence about the British fortifications, as well as the number and placement of enemy troops. Hale made detailed, to-scale drawings and recorded notes in Latin and hid them in the soles of his shoes.

On Sept. 21, 1776, Hale made his way to a tavern in Long Island. Upon completing his mission, he was to rendezvous with American forces the next day aboard the Schuyler.

Hale, however, had struck up a conversation with a friendly “fellow American soldier” while dining at the tavern. The two seemed to hit it off, and the subject quickly turned to the war.

What Hale didn’t know was that this friendly American soldier was neither friendly nor American. He was Colonel Robert Rogers – well known among his British soldiers as a ruthless, calculating man, a man filled with “evil as ‘deep as hell itself.'” Before long, Hale found himself outside the tavern with a posse of British guns in his face. Nathan denied his mission and tried unsuccessfully to maintain his persona as a schoolmaster.

Nathan Hale’s execution was scheduled for the very next day; he was given no trial. While waiting for his sentence to be carried out – death by hanging – he asked for the presence of a chaplain. His request was denied. He then asked for a Bible. That request, too, was denied. But Nathan’s presence in the British camp had caused quite a stir on “account of his high personal character.”

As Nathan mounted the ladder in the old apple orchard before a watching, sometimes wailing, crowd, his executioners asked if he wished to make any last confession. Nathan firmly replied, “I am so satisfied with the cause in which I have engaged that my only regret is that I have not more lives than one to offer in its service.”

Hale was left for three days to rot in the hot autumn New England sun, then buried in an unmarked grave.

Technically speaking, Nathan Hale’s mission was a failure. Yet Hale’s last words – often truncated and misquoted – set him apart as a dedicated, loyal son of Liberty, a true patriot among patriots.

For more on the story of Nathan Hale, read the full account on the Leben website.

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