Nathan Hale

Nathan Hale (June 6, 1755 – September 22, 1776) was a graduate from Yale College and a schoolteacher from Connecticut that served in the Continental Army as a spy. He is remembered for saying, “I only regret that I have but one life to give for my country” which is more legend than it is fact. Hale was hanged in 1776, but his death did aid George Washington in creating a proper spy ring throughout New York City.

Early Life

Hale was born on June 6, 1755 in Coventry, Connecticut. All reports point to him being a handsome and respectable man who was studious in his early education. His mother died when he was young and his father supported he and his brothers. His mother’s family aided in his education and began to prepare him for entry into Yale where he would study to become a minister. Nathan did not share those ambitions and upon his graduation became a schoolteacher.

While at Yale he met Benjamin Tallmadge who became one of his closest friends. Tallmadge was not a good influence on Hale and his studies. He was well-educated and found the early years of studying somewhat boring which led to him getting into trouble. He accumulated many fines and was sent a letter from his father that urged him to put away his vices and focus on his schoolwork. This did not mean that Hale was always indisposed. He participated in debating societies and gained popularity among the women present when he and Tallmadge debated in favor of women’s rights.

Nathan Hale seemed to be fond of a young woman named, Alice Adams. The two had met before and Nathan grew fond of her, but she was betrothed to Elijah Ripley. Ripley was an older man with a large fortune, but as providence would have it would die before the two would be married. Nathan waited the proper amount of time before speaking to her. His first correspondence came to her in the form of  a poem.

Alicia, born with every striking charm,
The eye to ravish or the heart to warm
Fair in they form, still fairer in they mind,
With beauty wisdom, sense with sweetness joined
Great without pride, and lovely without art…

He and Alice would enjoy each other’s company quite often and it seemed as if Nathan was ready to make Alice his wife, but he was an American patriot and his country needed him. After the battles of Lexington and Concord and the battle of Bunker Hill had been fought Nathan signed up for the Continental Army. He had shared his passions with Alice and his friend Benjamin.

American Revolutionary War

Nathan Hale was commissioned as a first lieutenant of the third company in the Seventh Regiment of Connecticut. He arrived on at Boston after the fighting had taken place and General Washington was laying siege to Boston. There was little action to be had and shortly after General William Howe abandoned Boston. Hale spent most of his time doing nothing but writing his lovely Alice, betting on fights, played checkers, and indulged in a bottle of wine at Brown’s Tavern. Life as a soldier was easy for Hale, but he was bored and sought to get into the action. The men of the seventh soon moved out towards Long Island.

He wrote to his brother Enoch on May 30 about the Tories present in New York saying, “it would grieve every good man to consider what unnatural monsters we have as it were in our bowels.” Hale’s opinions were never secret and it was known quite well where he stood on the issue of American independence from Britain. He was an ardent patriot from a well-known family in Connecticut.

While in Long Island, General Washington faced the impossible task of defending the important city with its valuable harbor without a Navy. Early in the campaign many of Washington’s subordinates lobbied the general to burn New York. Nathanael Greene laid out an argument as to the reasons why they should burn it and in every aspect was right, but his opinion was ignored for sentimental reasons and not military ones. The British arrived shortly and launched a series of effective attacks on the Continental Army that resulted in them fleeing the battlefield. Washington was able to retreat and save his army, but was left without knowledge of the full power of the British forces.

Hale Volunteers As a Spy

After Washington’s Retreat from New York he was left without a “channel of information” and sought to create that channel through Generals William Heath and George Clinton. There had been previous attempts to infiltrate New York, but all had not delivered much valuable information. The most valuable information was given to the Continentals by Lawrence Mascoll who gave approximations Howe’s strength, problems with army supply, and an attack on New Jersey. Mascoll’s information was correct with exception to the attack on New Jersey, but it still left Washington blind to Howe’s movements. The channel in which Heath and Clinton were supposed to open also gave faulty information or nothing of relevance. Washington had to search for another option.

Nathan Hale had grown bored by the lack of action and asked for a transfer to a different unit that was under lieutenant colonel Thomas Knowlton. George Washington came to Knowlton and began making plans for another mission of espionage. Learning of this plan Hale visited his long time friend, William Hull, and inquired about becoming a spy. He asked Hull to speak candidly which Hull did. He said that being a spy was a “murky” affair and required much stealth. Hull said that he did not believe Hale had the character qualities necessary to be a spy due to his strong opinions and inability to keep them to himself. Still Hale insisted that he had not served his country in any worthwhile capacity since joining the army ranks a year earlier and longed to give something to his country. Hull did his best to discourage him, but it became clear that Washington would soon have a volunteer.

Nathan Hale met with George Washington twice before the fateful mission. The two established a cover story, mission objective, route, and other things necessary for his success. While these meetings were not public knowledge it is clear that the two did not go to great measures to make them secret. Hale’s mission was to scout Long Island and return to Washington and give him the details. After a bit of planning Hale set off to Connecticut. It was the last time that his long-time friend William Hull would see him alive.

Nathan Hale’s Mission Timeline

Nathan Hale has been romanticized in American History for his sacrifice. He has been made to be a hero who bravely faced the gallows and was caught just before he was able to cross into safety. While he deserves credit for his bravery the mission was a fiasco and Hale was under supervision shortly after his feet landed on British occupied soil. His mission lasted only seven days and he was watched from afar for six of them. He conversed and was tricked by the very man who was watching him and the evidence was so overwhelmingly against him that a trial was unnecessary which meant his hanging occurred the next day. While glorified in the history books it was an embarrassment to General Washington who never spoke of it again.

September 11 – 14: It is unclear to the exact date that Hale left the Continental Army camp, but it definitely happened during this timeframe.

September 15: Nathan Hale and Sergeant Stephen Hemptstead arrived in Norwalk, Connecticut. Hemptstead recalled later that Hale was dressed as a Dutch schoolteacher and only carried with him his degree from Yale and orders from General Washington that permitted him access to any resource to use for carrying out the mission. Hale searched out Captain Charles Pond who captained the Schuyler. 

September 16: Pond ferried Hale across the Sound and dropped him off in Long Island. The British Captain William Quarme learned of the movements of the Schuyler and set out to find intercept it. He arrived too late, but still suspected that the Schuyler had dropped off something or someone. He informed Robert Rogers, the commander of Rogers’ Rangers, who suspected a spy and had a large pool of information in that area to draw from. He was unable to arrive in Long Island to track Hale until September 18.

September 18 – 21: Rogers began to research his information channels and learned of a suspicious character that arrived as a schoolteacher. Rogers’ quickly finds Nathan Hale and puts him under surveillance. He kept a close eye on him and noticed that he took notes after every time he saw a British detachment. He believed that he needed more evidence to convict Hale so he continued to track him. That night Hale stayed at a roadside tavern. Rogers arrived and sat a table away and began to make small-talk. He was soon able to convince Hale that he was a friend who supported the cause of liberty. Hale and he toasted to American Independence and Rogers asked if they could dine together in the morning.

The next morning Hale met Rogers and four other men dressed in civilian clothes and explained to Hale that they were friends of the cause. Once Hale spoke of his mission to Rogers and his men, Rogers signaled for his capture and accused him of being a spy which Hale unconvincingly denied. The evidence was incredible. They had found maps and notes and Hale had spoken of his mission to Rogers and four others. Hale was marched to Flushing where Rogers guarded him and then was given to Howe that evening. Howe quickly signed Hale’s death warrant.

September 22: Nathan Hale was taken to an artillery park which is now Third Avenue and Sixty-sixth Street. He was marched up the gallows where he spoke his last words. His words were not the famous, “I regret that I have but one life to lose for my country.” These lines came from William Hull who was not present at Hale’s execution. What Hale really said was written by Captain Frederick MacKenzie who spoke well of Hale’s conduct, “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.” Later that night during a prisoner exchange General Washington learned of Hale’s death.

September 30: Hale’s brother Enoch learned of Nathan’s death.

The entire thing was a debacle from the start, but Hale’s death was not in vain. Unfortunately for him General Washington made many mistakes, but he did not repeat them. He again began to pursue intelligence which led to the most successful spy ring in the American Revolutionary War that helped expose Benedict Arnold. The spies would become known as the Culper Spies.


1. Rose, Alexander. Washington’s Spies: The Story of America’s First Spy Ring. New York, New York: Bantom Dell, 2006