Nathan Hale was a young man who had every prospect for a happy and fulfilling life. Contemporary accounts indicate that he was kind, gentle, religious, athletic, intelligent, good looking and as one acquaintance testified, “the idol of all his acquaintances.” Both men and women commented on his striking appearance. He had fair skin and hair, light blue eyes, and stood just under six feet tall. No wonder it was said that all the girls in New Haven were in love with him. While many were impressed by his kindness and strong Christian ideals, he was also known for his skill in wrestling, football, and broad jumping.

Yet in spite of the above, this remarkable young man ended his life in the most ignominious manner known to his era: death by hanging – the ultimate degradation – reserved only for the most despicable of criminals. He risked this fate willingly to serve a cause as yet unproven or established, a cause more likely to be soon annihilated. Nathan Hale is representative of many young eighteenth century professionals who were obsessed with being of service for the public good, who – foreshadowing a twentieth century brand of patriotism – asked not what their country could do for them but rather what they could do for their country.

Nathan Hale of Coventry, Connecticut was born in 1755 into two respectable New England families. His parents, Richard Hale and Elizabeth Strong Hale, were staunch Puritans who believed in religious devotion, work ethic, and education. The sixth of ten surviving siblings, he was tutored by the local minister, Rev. Dr. Joseph Huntington, who greatly influenced his love of learning. In 1769, both Nathan and his brother, Enoch, were sent to Yale College at the ages of 14 and 16, respectively. They became part of the shining Class of 1773, many of whom were destined to have remarkable careers in the service of their country, their state, and their communities.

During his college years, Nathan was exposed to the cosmopolitan atmosphere of New Haven and to many new, progressive ideas of the eighteenth century. It was doubtless a different world from the isolated farming community where he had been raised. Both brothers belonged to the literary fraternity, Linonia, which debated educational topics and issues of the day – including astronomy, mathematics, literature, and the ethics of slavery. Meetings were held in the students’ rooms at New College – a large brick dormitory in the center of campus. This beautiful building, where Nathan and Enoch were roommates, still stands on the Yale campus (Connecticut Hall). His time was full of activity, strong friendships, and varied interests, including helping to establish Yale’s first secular library. Nathan graduated from Yale with first honors at the age of eighteen, participating in the 1773 commencement debate: Whether the education of daughters be not without any just reason, more neglected than that of sons.

Like many young graduates, Hale took a position teaching school – first in East Haddam and later in New London, Connecticut. In rural East Haddam, however, Hale appears to have been lonely, missing the lively company of his college friends. New London was definitely more to his liking – it even had a newspaper, liberal in character, published by Timothy Green, a proprietor of the Union School. His classes consisted of about thirty young men who were taught Latin, writing, mathematics, and the classics. In 1774, he also conducted a summer school for young ladies from 5 to 7 AM. That the young ladies of New London were willing to attend a 5 AM class in the classics was perhaps more a tribute to the schoolmaster’s good looks that any attraction to the subject at hand. Although he never appears to have been serious about marriage, during 1774 he was teased by two former classmates about an infatuation with his landlord’s niece, Elizabeth Adams. Although Elizabeth married in 1775, in 1837 she wrote a stunningly beautiful remembrance of her friend, Nathan Hale, then dead for sixty-one years.

Nathan enjoyed teaching and his mild manner of imparting knowledge was greatly appreciated by both students and parents alike. Consequently, in late 1774 he was offered a permanent teaching position as the master of the Union School and it appears that he intended to make teaching his profession. During this same year, he also joined a local militia and was elected first sergeant. While his amiability made him many delightful acquaintances among the town’s best families, nineteen-year old Nathan Hale also continued several close friendships with his former Yale classmates. Their surviving letters tell of the joys, frustrations, romances, and boredom experienced by young people on the threshold of life and painfully impatient for it all to unfold. By the spring of 1775 therefore, civic-minded Nathan Hale had many interesting friends, a great job that he enjoyed, perhaps a girl friend (or more), and an enjoyable life in a bustling cosmopolitan seaport city. Everything was going his way.

When war broke out in April, many chapters of Connecticut militia rushed to Massachusetts to help their neighbors during the Siege of Boston. Hale’s militia marched immediately but he remained behind – perhaps because of his current teaching contract which did not expire until July, 1775. Or perhaps he was unsure. Contemporary letters tell of the conflict that went on in his friends’ minds – doubtless mirrored in his own – whether to join the new army and fight in Boston or to keep quiet and wait. This was not the clear decision we all see today and these young professionals had a lot to lose. The new master of a prestigious private school does not without considerable risk take on the label of rebel and traitor.

In July 1775, Nathan received a heartfelt letter from classmate and friend, Benjamin Tallmadge. Always the pragmatist, Tallmadge had gone to see the Siege of Boston for himself. Upon his return, Ben poured out his heart in a letter to Nathan dated July 4, 1775 – the last year that date would be just another day. After analyzing the pros and cons of joining up, Tallmadge finally told Nathan that, in spite of his friend’s engagement in a noble public service (teaching school), “Was I in your condition ... I think the more extensive Service would be my choice. Our holy Religion, the honour of our God, a glorious country, & a happy constitution is what we have to defend.” The day after receiving Tallmadge’s letter, Nathan Hale accepted a commission as first lieutenant in the 7th Connecticut Regiment under Colonel Charles Webb of Stamford.

Stationed at Winter Hill, Hale enjoyed military life and threw himself wholeheartedly into the duties of a company commander, trying to be a good officer, yet yielding to and clearly enjoying the new, macho experiences of camp life. Like most young soldiers, he complained about his superiors and worried about his subordinates – on one occasion offering his own salary to his men if they would stay in the army another month. Still – he told his friends – he was enthusiastic, happy to be there, and wouldn’t accept leave even if he could get one.

When Washington reorganized the army, Nathan received a captain’s commission in the new 19th Connecticut Regiment and – to his credit – several men asked to be placed under his command. In the spring of 1776, the army moved to Manhattan to prevent the British from taking New York City. Nathan spent six months at Bayard’s Mount building fortifications and preparing for the inevitable battle. When the British invaded Long Island in August, 1776, Hale had still not seen combat and his regiment also missed fighting in the Battle of Long Island. After almost a year in the army, he had kept records, drawn supplies, written receipts, and supervised guard duty. These were not the daring exploits young men dreamed of when they went to war.

At the beginning of September 1776, with the British in command of Western Long Island and the rebel army trying to defend Manhattan, Washington formed The New England Rangers, an elite, green beret-type unit under Lt. Col. Thomas Knowlton. Hale was invited to command one the four companies assigned to forward reconnaissance around the Westchester and Manhattan shorelines. Meanwhile, Washington desperately needed to know the site of the upcoming British invasion of Manhattan Island. The best way to obtain this pivotal information was to send a spy behind enemy lines but in honor-conscious eighteenth century minds, spying was considered to be a demeaning, dishonest, and indecent activity – unworthy of a gentleman.

Nevertheless, Knowlton persuaded Nathan Hale to volunteer for this spy duty behind enemy lines. Before leaving, Nathan asked his fellow officer and friend, Captain William Hull, for advice. Hull tried hard to dissuade him from the dangerous and controversial mission but in the end Nathan justified it by saying that any task necessary for the public good became honorable by being necessary. This was finally his chance to do something valuable to the patriot cause.

Accompanied by his sergeant, Steven Hempstead, Hale left Harlem Village in early September and headed north along the East River. Although armed with an order allowing him to commandeer any armed American vessel, Hale was prevented from crossing to Long Island by numerous British ships on patrol. He finally found passage at Norwalk, Connecticut and crossed the Long Island Sound in a rebel longboat. Leaving his uniform, commission, silver shoe buckles and other personal possessions with Hempstead, Nathan Hale slipped into the darkness at Huntington Bay, Long Island and dropped out of sight – both to his friends and to history.

He doubtless spent several days behind enemy lines in his contrived disguise as an schoolmaster looking for work. Before he could return with any useful information, however, the British invaded Manhattan at Kip’s Bay (East River at 34th Street), taking most of the island on September 15th and 16th. His mission negated, Hale may have crossed into British-occupied New York City presumably to gain whatever intelligence he could for Washington, who was now entrenched behind the bluffs at Harlem Heights. On September 20th, New York City was set on fire, causing confusion, rioting, and a heightened alert for rebel sympathizers. By this time, Hale is thought to have returned to Long Island for a planned rendezvous with the longboat. On the evening of September 21, 1776, he was somehow stopped, perhaps near Flushing Bay, Long Island, by the Queen’s Rangers, a new company of Loyalists led by Lt. Col. Robert Rogers (of Northwest Passage fame).

The circumstances of his capture have never come to light although many theories have been proposed. Almost immediately after Hale’s death, rumors flew that he had actually been recognized while undercover by his first cousin, Samuel Hale, a dedicated Loyalist then working for the British in New York. Samuel denied these allegations and what part, if any, he had in his cousin’s fate has never been substantiated.

Nathan Hale was immediately brought for questioning before the British commander, General William Howe, who had just moved into the Beekman Mansion (51st Street and 1st Avenue). Intelligence information was found on his person and since this was not in code or invisible ink, he was irrevocably compromised. Hale identified himself, his rank, and the purpose of his mission, perhaps to regain a semblance of an honest soldier (rather than a spy). Although Howe was moved by the young man’s demeanor and patriotism, he was out of uniform behind enemy lines. The customs of war were clear and Nathan was sentenced to hang the next day.

A tradition says that Hale spent the night confined in a greenhouse on the Beekman estate and that he was denied a minister or even a bible by the provost marshal, an unsavory character named William Cunningham. The next morning, Sunday, September 22, 1776 at 11:00 AM, Nathan Hale was marched north, about a mile up the Post Road to the Park of Artillery. It was located next to a public house called the Dove Tavern (66th Street and 3rd Avenue), about 5 1/2 miles from the city limits. After making a “sensible and spirited speech” to those few in attendance, the former schoolteacher and Yale graduate was executed by hanging – an extremely ignominious and horrible fate to one of his time and class.

Whether Hale said that he only regretted having one life to lose for his country has been debated. The quote comes from a British engineer, John Montresor, who kindly sheltered Nathan in his marquee while they were making preparations for the hanging. Hale entered and appeared calm, asking Montresor for writing materials. He then wrote two letters – one to his favorite brother and classmate, Enoch Hale, and the other to his military commander (these letters have never been found and were probably destroyed by the provost marshal).

Captain Montresor witnessed the hanging and was touched by the event, the patriot’s composure, and his last words. As fate would have it, Montresor was ordered to deliver a message from General Howe to Washington (under a white flag) that very afternoon. While at American headquarters, he told Alexander Hamilton, then a captain of artillery, about Hale’s fate. Captain Hull found out and went with the delegation returning Washington’s answer to Howe whereupon he managed to speak with Montresor. The British engineer told Hull that Nathan had impressed everyone with his sense of gentle dignity and his consciousness of rectitude and high intentions. Montresor quoted Nathan’s words on the gallows as: “I only regret that I have but one life to lose for my country.”

This elegant statement, doubtless paraphrased from Addison’s popular play, Cato, is the quotation best remembered from the execution of Nathan Hale. He must have been telling the British that his cause still had great merit and that someone like himself – intelligent, educated, and decent – was willing to die for it without regret. It should be put in prospective that the cause was in bad shape in September 1776. The much-defeated and demoralized rebel army had been chased into upper Manhattan, ripe for total destruction by the vastly superior British forces. Its soldiers were deserting in droves now – sometimes whole companies at once – and the end seemed only a matter of time. But Hale told the British straight – standing on the gallows – that his country was still worthwhile and worth dying for.

William Hull later told the world about his friend’s patriotism, bravery, and sacrifice; however, since Hull’s account is not that of an eyewitness, many historians have denied his story as a unsubstantiated folk legend. If this is true, it means that either Montresor or Hull lied about Hale’s last words, which seems like a strange thing for either of them to do. From a practical standpoint, it is hard to believe that Hale would have been so well remembered had he not distinguished himself in some outstanding manner at his execution. He was a junior officer of no significance and even his brief spy mission had failed.

Another credible statement purporting to be from Nathan Hale’s execution is found in the diary of Lt. Robert MacKensie, a British officer in New York at the time. The diary entry was made on the very day of Hale’s execution, September 22, 1776: “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.” This indicates that Hale wanted to be remembered as a soldier under orders and not a spy.

In conclusion, an insignificant schoolteacher who never wrote anything important, never owned any property, never had a permanent job, never married or had children, never fought in a battle and who failed in his final mission – made history in the last few seconds of this life. He is to be admired because of his courage in accepting a difficult mission (both dishonorable and dangerous) that he did not have to do. Then he had the cool and presence of mind to set the British straight about American patriotism, literally in the shadow of the gallows. We don’t know what exactly he said, but it must have been impressive and Hale deserves to be remembered for his genuine dedication, his courage, and his willingness to pay the price with honor and dignity.

Nathan Hale’s body was left hanging for several days near the site of his execution and later was buried in an unmarked grave. He was 21 years old.”