“Swing the rebel off!”

The ladder toppled from under the prisoner’s feet. He hung, struggling, suffocating from a hangman’s noose, tied taut to an apple tree in a colonial orchard. Nathan Hale, America’s first spy, was dead.

Nathan Hale was the son of a prosperous Connecticut farmer, Richard Hale. The Hales were a deeply pious family. Even their contemporaries regarded the Hales as a distinctly Puritan family, though that appellation had fallen out of use some time earlier. Bible and prayer book reading ended the Hales’ day. And Richard Hale ensured that Nathan, along with his brother Enoch, would have an education befitting those who might one day pursue the ministry. Nathan entered Yale at the age of fourteen and studied logic, languages, law, literature, and theology. Yale wasn’t all work and no play for Nathan, however. There, he excelled in such physical exploits as wrestling and “football.” And young Nathan was an active member of Linonia, a secret fraternity at Yale, where members debated politics, discussed literature, and dissected such hot topics as slavery and women’s rights.

By all accounts, Nathan was a remarkably handsome young man. He was tall, much taller than the average male of his day, and his sandy brown hair and light eyes attracted much attention from the ladies, which Nathan didn’t seem to mind. Nathan was also just a bit mischievous. Once, when Nathan and Enoch were supposed to be using their father’s hard-earned funds to take care of their basic necessities while at Yale, Nathan instead had to use the money to replace a string of windows at the college he had broken in a prank. Richard Hale, understanding the pressures of college life even in 1773, wrote to his sons,

Dr. Eneas Munson, Hale’s mentor while at Yale. By William Jennys, 1790. Courtesy Cushing Whitney Medical Library

I have nothing special to write but would by all means desire you to mind your Studies and carefully attend the orders of College. Attend not only Prayers in the chapel but Secret Prayer carefully. Shun all vice, especially card playing. Read your Bibles a chapter a night and morning . . . .1Phelps, M. William, The Life and Death of America’s First Spy: Nathan Hale (New York: St. Martin’s Press, 2008), 21.

Though Nathan had garnered the reputation of a frolicking, card-playing mischief-maker, M. William Phelps’s masterful biography of Hale recounts an additional assessment of the young Hale. Dr. Eneas Munson, Hale’s mentor while at Yale, confessed, “That man is a diamond of the first water, calculated to excel in any situation he assumes. He is a gentleman and a scholar—last though not least of his qualifications, a Christian.”2Ibid., 27.

Nathan graduated from Yale in 1773 and took a teaching position in New London, Connecticut. He was committed to education and was well loved by his pupils. In keeping with his Puritan upbringing, Hale believed his calling of teaching just as worthy as that of the ministry. Years after Hale’s death, one of his acquaintances reminisced that Hale’s “capacity as a teacher, and the mildness of his mode of instruction, were highly appreciated both by parents and pupils” and that Hale himself was “peculiarly free from the shadow of guile.”3Stewart, I.W., Life of Captain Nathan Hale, The Martyr-Spy of the American Revolution (Hartford: F.A. Brown, 1856), 35.

The political climate of Nathan Hale’s day was tense, even turbulent. The promise of war hung heavy like low storm clouds over New England. Although faithful in his teaching duties, Nathan was deeply troubled by Britain’s aggressive behavior, and he desired to perform a more active service for his homeland. In a town meeting, just days after shots were fired at Lexington and Concord, local leaders in Nathan’s small town found themselves responding to the call for dedicated patriots to take up arms against British aggression. Nathan delivered a rousing, impromptu speech to the men of the town and closed with a call to action: “Let us march immediately and never lay down our arms until we obtain our independence.”4Johnston, Henry Phelps, Nathan Hale, 1776, Biography and Memorials, (New Haven: Yale University Press), 65. Available at http://books.google.com/books?id=UqJ2AAAAMAAJ&printsec=frontcover&dq=nathan+hale+1776&ei=cAucS9vWH4bklQT5pKjuCQ&cd=1#v=onepage&q=&f=false In a few short months, once Nathan had fulfilled his teaching contract, he was commissioned a lieutenant in the Connecticut militia.

Yale College, engraving from 1749

The early portion of Nathan Hale’s military service was relatively tame. The young man was quickly promoted to captain of the Seventh Regiment’s Third Company because of his excellent command of language and history. And much of Hale’s service was spent turning rag-tag bands of men into disciplined soldiers. Hale’s journals recount the mundane duties of the soldiering life—drills, skirmishes, deprivations. Hunger and grave illness took its toll on the American forces. Many a time, Nathan would find himself making pleas for better pay for his men or kneeling in prayer beside the bed of a wasting soldier. He was all too sensible to the harsh realities of fighting a much superior foe. Desertion, sadly, was commonplace early on in the war effort. In an effort to retain the disillusioned soldiers under his command, Hale promised them his own wages “if they would tarry another month.”5Stuart, 62.

The notion of duty was one that hounded Nathan for much of his military career. Hale was frequently frustrated with not being able to engage the enemy more directly. He wrote in a journal entry,

It is of the utmost importance that an Officer should be anxious to know his duty, but of greater that he should carefully perform what he does know: The present irregular state of the army is owing to a capital neglect in both of these.6Johnston, 246.

And the next day he wrote:

A man ought never to lose a moment’s time. If he put off a thing for one minute to the next his reluctance is but increas’d.7Ibid., 246.

Nathan’s opportunity to “carefully perform what he does know” came at a critical moment for Nathan and his company, for hunger was a constant plague for the colonial armies. A British warship, the Asia, was harbored off the coast of Governor’s Island in New York, laden with food and supplies. Under cover of a thick November darkness, Nathan led his men on small boats across the waters and in a bold move, boarded the ship, forced its crew into the hold, and commandeered the ship with its contents for the rebel army. Perhaps Nathan’s sense of duty was fueled by a recent sermon he had heard titled, “For how can I endure to see the evil that shall come upon my people? Or how can I endure to see the destruction of my kindred?”8Phelps, 103. Based on Esther 8:6, this sermon struck a chord with Nathan and, in a sense, foreshadowed the future events of his short life.

The Battle of Long Island by Alonzo Chappel (1828-1887) Courtesy The Brooklyn Historical Society

New York was a critical piece in the puzzle of the colonial war effort. 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 could effectively cut Washington off from the southern and western forces of the American army, along with much-needed munitions and foodstuffs. Then the British would have free course into the heart of the continent, into the very center of the American forces, and there would be little stopping them. Although Washington’s army was some 20,000 strong, the men—and boys—were ill-equipped to withstand another harsh New England winter. To make matters worse, a savage outbreak of smallpox decimated the ranks of Washington’s soldiers. More than ever, it was critical to ferret out the designs of the British, to anticipate their next move. 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 it was one with ignominious associations. If a spy was caught, there would be no honorable death—he was destined only for the hangman’s noose. Though there was no official organization for the training of spies (spying was looked down upon by both sides as the worst of wartime criminal activity, short of treason), Thomas Knowlton, Lieutenant Colonel in the American army headed up an elite force of soldiers, called Rangers, handpicked for particularly dangerous missions. And Nathan Hale, along with his brother Enoch, was inducted into this group. Washington called on Knowlton’s Rangers to gather the intelligence he needed.

The Delaware Regiment at the Battle of Long Island

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 Nathan reportedly “almost immediately” volunteered. Here, at last, was an opportunity for Hale to serve in a measurable, meaningful way.9Ibid., 142. 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, and he was incapable of acting a part equally foreign to his feelings and habits.”10Ibid., 143.

Nathan, however, would not waver. He believed it was God’s will to serve his country, even if it meant his own personal humiliation. Nathan replied to 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. I am fully sensible of the consequences of discovery and capture in such a situation, but for a year I have been attached to the army and have not rendered any material services while receiving compensation for which I make no return. Yet I am not influenced by any expectation of promotion or pecuniary award; and every kind of service necessary for the public good becomes honorable by being necessary.11Lossing, Benson John and Anna Seward, The Two Spies: Nathan Hale and John André, (Harvard University: D. Appleton and Co. 1886), 15. Available at http://books.google. com/books?id=89uQ4KKRVJMC&printsec=frontcover#v=onepage&q=&f=false

Walter Korder (1891-1962), Capture of Nathan Hale, Pencil, 12 x 15 in., New Britain Museum of American Art, Friends Purchase Fund, 1975.74 LIC

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 their potential attack scenarios 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 September 21, 1776, Hale made his way to a tavern in Long Island. No doubt he enjoyed a hearty meal and generous drafts of ale. His mission was complete, and he was to rendezvous with American forces the next day aboard the Schuyler.

Early biographers of Hale surmise that the young soldier was recognized by his Tory-sympathizing cousin, Samuel Hale, and subsequently turned over to the British forces. Some years later, however, a journal belonging to a British loyalist, Consider Tiffany, was unearthed, and its contents shed new light on the capture and arrest of Hale. Nathan, a newcomer with a thin cover story, had been seen about town before and suspicions were mounting against him. He was, after all, strikingly tall and handsome, and asking a lot of questions; such a man would hardly go unnoticed. Tiffany’s journal notes that Hale had struck up a conversation with a friendly “fellow American soldier” while dining at the tavern.12Phelps, 173. The two seemed to hit it off, and the subject quickly turned to the war. What Hale didn’t know, however, 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.'” Whether Nathan had too much to drink or just felt relaxed and comfortable with a fellow soldier, we don’t know. But at some point in their conversation, Nathan, as Phelps’s biography points out, “began to candidly talk about his mission, ‘informing Rogers of his business and intent.’ ” 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.

John Montresor, by John Singelton Copely, 1771. A British military engineer, Captain John Montresor witnessed the hanging of Nathan Hale.

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.”13Ibid., 187. 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.14Ibid.,192.

Phelps writes,

Nathan hung for three days, his flesh rotting in the unseasonably hot September sun as his corpse was mocked and spat on before a slave finally cut his body down and buried it, reportedly unclothed. Thus was America’s first spy of the Revolution in-terred….without ceremony or formal prayer inside a shallow, unmarked grave.15Ibid.,193

Technically speaking, Nathan Hale’s mission was a failure. He was caught, summarily executed, and the information he gathered was ultimately irrelevant. At the time of his death, Hale was not hailed as a martyr or a great soldier. He was a junior officer with little experience and no particularly remarkable exploits to his name. Yet Nathan Hale’s last words—often truncated and misquoted—set him apart as a dedicated, loyal son of Liberty, a true patriot among patriots.


1 Phelps, M. William, The Life and Death of America’s First Spy: Nathan Hale (New York: St. Martin’s Press, 2008), 21.
2 Ibid., 27.
3 Stewart, I.W., Life of Captain Nathan Hale, The Martyr-Spy of the American Revolution (Hartford: F.A. Brown, 1856), 35.
4 Johnston, Henry Phelps, Nathan Hale, 1776, Biography and Memorials, (New Haven: Yale University Press), 65. Available at http://books.google.com/books?id=UqJ2AAAAMAAJ&printsec=frontcover&dq=nathan+hale+1776&ei=cAucS9vWH4bklQT5pKjuCQ&cd=1#v=onepage&q=&f=false
5 Stuart, 62.
6 Johnston, 246.
7 Ibid., 246.
8 Phelps, 103.
9 Ibid., 142.
10 Ibid., 143.
11 Lossing, Benson John and Anna Seward, The Two Spies: Nathan Hale and John André, (Harvard University: D. Appleton and Co. 1886), 15. Available at http://books.google. com/books?id=89uQ4KKRVJMC&printsec=frontcover#v=onepage&q=&f=false
12 Phelps, 173.
13 Ibid., 187.
14 Ibid.,192.
15 Ibid.,193