Captain Nathan Hale: A Tory’s Account of the Arrest and Execution of the First American Spy

An idealized bronze statue honors the heroism of Yale College graduate Nathan Hale (1755-1776; B.A. 1773, M.A. 1776), a young schoolteacher captured and executed by the British during the American Revolution. Hale’s youth and defiant last words, inscribed on the statue’s base, made him a national hero, and his legend remained powerful over a century after his death when alumni donated this monument. Unable to afford the renowned Gilded Age sculptor Augustus Saint-Gaudens, they commissioned the piece from his former assistant, Bela Pratt, who had studied at the Yale School of the Fine Arts under John Ferguson Weir. Combining dignity and beauty with a traditional martyr pose, Pratt’s statue stands beside Connecticut Hall, where Hale lived as a student. / Photo by Christopher De Coro, Wikimedia Commons

By Dr. James Hutson
Chief of the Manuscript Division
Library of Congress

Serendipity is one of the joys of working with manuscript collections. Scholars and archivists never know when they might find an unexpected gem of a document buried in a collection, newly acquired or newly accessible, which will alter a long accepted interpretation, expose a hypocrite or vindicate a hero. The Library of Congress has recently obtained just such a document, a manuscript history of the American Revolution written during or soon after the conflict by a Tory storekeeper in inland Connecticut with the quintessentially New England name, Consider Tiffany.

Held under house arrest by local authorities for 15 months during the Revolution, Tiffany is still remembered in his native town of Barkhamstead, Conn., for his feisty non-conformity. Few, however, outside members of his immediate family, knew that Tiffany had written a history of the American Revolution. The manuscript was handed down from one generation of Tiffanies to another until it was donated to the Library of Congress in 2000 by the current representative of the family, G. Bradford Tiffany.

The Library of Congress was eager to acquire Consider Tiffany’s history because, with the exception of the intemperate account of the pre-revolutionary years in Massachusetts by the colony’s Loyalist chief justice, Peter Oliver, and, more tangentially, the history of Connecticut to 1781 by the Reverend Samuel Peters, there are no New England Tory histories of the American Revolutionary period. Tiffany’s manuscript would, therefore, be a welcome addition to the Library’s collections, because it would present a point of view virtually absent from the literature of the American Revolution.


Left, this statue, “Nathan Hale: Civic Virtue” by Frederick William MacMonnies, stands in a New York fountain and is one of many tributes to America’s first spy; center, this statue of Nathan Hale on the campus of Yale University was designed by Bela Lyon Pratt and erected in 1913; right, Maj. Robert Rogers played a key role in the capture of Nathan Hale.

But there were questions about the acquisition. How much could a Connecticut country storekeeper know about the dauntingly complex story of the American Revolution? Tiffany, it turned out, knew plenty about the Revolution. In particular, he knew and inserted in his history a startling story, which, if true, would solve one of the enduring mysteries in American history, involving one of our noblest national heroes: how, where and by whom was Nathan Hale captured?

Hale needs no introduction. He is the “martyr-spy” of the American Revolution and the patron saint of the American intelligence establishment; his statue stands today just off the main lobby of CIA headquarters in McLean, Va. As a 21-year-old captain in the Continental Army whose spotless moral character was universally admired, Hale courageously volunteered in September 1776 for the dangerous mission of reconnoitering British army positions in the New York City area; he was captured and hanged on Manhattan Island on Sept. 22, 1776. Ardent patriot writers of the 19th century depicted Hale’s death in theological tones, describing how the young hero, alone amidst a sea of hostility, established a moral superiority over his tormentors and died triumphantly, uttering the imperishable sentiment: “I only regret that I have but one life to lose for my country.”

There is no contemporary evidence that Hale uttered these exact words; in fact, much of what has been written about his fateful mission is based on inference, guesswork and flights of imagination. Two professional intelligence officers turned historians, Maj. Gen. E.R. Thompson and G.J.A. O’Toole, have recently studied Hale’s mission and have found all accounts of it to be suspect.

Thompson observed that there were “a very few nuggets of hard intelligence and a great deal of … outright speculation.” Hale, he writes, went ashore on Long Island “in the pre-dawn hours on an unknown date in mid-September and disappeared from sight. … The next hard evidence of his whereabouts did not come until September 22d,” i.e., the day he was hanged. O’Toole was also impressed with how little we know about Hale’s mission. “Where he was captured,” he writes, and “more to the point, why, remain matters of speculation.”

The “hard intelligence” whose paucity Thompson lamented consists of three statements by British soldiers on the fateful 22nd of September. An orderly book reported that Hale was “apprehended last night,” i.e., Sept. 21, confessed and was hanged on the 22nd at 11 a.m. An entry in the diary of a British officer, Lt. Frederick Mackenzie, confirmed these facts and added the significant information that Hale was captured on Long Island, as Lafayette later confirmed. The third piece of hard evidence surfaced in 1933 in a diary entry by Capt. William Bamford of the 40th Regiment of Foot, which added more information: Hale, Bamford reported, was “taken by Major Rogers.”

Scholars have recognized that this last-named individual can have been none other than Maj. Robert Rogers, the daring New England frontiersman and guerrilla commander whose “prodigious feats of valour” in the French and Indian War were celebrated by Kenneth Roberts in his popular novel “Northwest Passage” (1937) and portrayed by Hollywood in a movie of the same name in which Spencer Tracy played the intrepid Rogers. After the war, Rogers, who had beaten a counterfeiting charge by joining the army, was court-martialed for treasonous dealings with the French but was exonerated at a trial in Montreal, where it was reported that he “drinks and games as usual.” He then went to London, hobnobbed with high society—”with cursed impudence” hissed an enemy—and worked every angle to enrich himself. He claimed to have campaigned briefly as a mercenary for the Bey of Algiers and tried to find backers for an expedition to discover the Northwest Passage. Rescued from a debtor’s prison by his brother, Rogers returned to America in 1775 and offered his services to the highest bidder.

Had the fates been a bit kinder to Hale, he might have met Rogers in December 1775, recognized him a few months later, and escaped the trap that cost him his life. In the fall of 1775, Rogers was in New Hampshire, sizing up land-speculating prospects. Unsubstantiated rumors spread that he had been seen in full Indian regalia, consorting with pro-British tribes. After visiting and offending his estranged wife in Portsmouth, he headed for Boston. By Dec. 14, 1775, Rogers had taken a room at a tavern in Medford, Mass., a short distance from Gen. George Washington’s headquarters at Cambridge, from which the general was directing the siege of Boston. In a letter to Washington of Dec. 14, 1775, Rogers asked “to pay you my respects personally.” Refusing to admit Rogers to camp, Washington dispatched Gen. John Sullivan to interview him at his Medford tavern.

Two pages of Consider Tiffany’s manuscript history of the American Revolution. The page on the left (verso) contains Tiffany’s account of the capture of Nathan Hale by Maj. Robert Rogers. – Manuscript Division

Between Dec. 14 and 17, Sullivan called on Rogers twice. Sullivan did not trust Rogers and advised Washington to shun the unsavory supplicant, whereupon Rogers left Medford for Albany, N.Y. During this precise period, Hale, who was serving with the Connecticut troops besieging Boston, was in Cambridge at least twice. Had Washington received Rogers at his headquarters, there is a distinct possibility that Hale, who was friendly with Putnam, Lee and other Washington comrades, might have met Rogers at a social function or in some other way. Washington and Sullivan evidently kept Rogers’ proximity to headquarters a secret. Hale, therefore, never knew how close his nemesis was.

Rogers eventually found his way in the summer of 1776 to Philadelphia, where he was imprisoned by the Continental Congress. Escaping in early July 1776, he made his way to the British fleet lying off New York and was commissioned by Gen. Howe to raise a battalion of rangers, patterned after his French and Indian war outfit. It was to be manned by Tories and other disaffected Americans. Rogers established his headquarters at Flushing, L.I., and spent most of September cruising Long Island Sound in a British sloop looking for fighting men. It was in his capacity as a recruiting officer that Rogers evidently crossed paths with Hale.

The first scholar who appears to have used Bamford’s diary (James Grafton Rogers, a distant descendant of Robert Rogers) integrated it with the results of historical research conducted by various residents of Long Island and concluded in 1941 that Rogers did, in fact, capture Hale, as Bamford asserted. How Rogers apprehended Hale the scholar did not venture to guess. Nor is Rogers’ best modern biographer, John Cuneo, willing to tackle this question. Accepting Bamford’s statement that Hale was “taken” by Rogers, Cuneo leans toward the theory that Hale may have been seized by persons unknown and that Rogers merely served as a kind of transit policeman, ferrying Hale from Long Island to British headquarters in Manhattan aboard his sloop.

Now enter Consider Tiffany with the following account:

[Rogers] “detected several American officers, that were sent to Long Island as spies, especially Captain Hale, who was improved in disguise, to find whether the Long Island inhabitants were friends to America or not. Colonel Rogers having for some days, observed Captain Hale, and suspected that he was an enemy in disguise; and to convince himself, Rogers thought of trying the same method, he quickly altered his own habit, with which he Made Capt Hale a visit at his quarters, where the Colonel fell into some discourse concerning the war, intimating the trouble of his mind, in his being detained on an island, where the inhabitants sided with the Britains against the American Colonies, intimating withal, that he himself was upon the business of spying out the inclination of the people and motion of the British troops. This intrigue, not being suspected by the Capt, made him believe that he had found a good friend, and one that could be trusted with the secrecy of the business he was engaged in; and after the Colonel’s drinking a health to the Congress: informs Rogers of the business and intent. The Colonel, finding out the truth of the matter, invited Captain Hale to dine with him the next day at his quarters, unto which he agreed. The time being come, Capt Hale repaired to the place agreed on, where he met his pretended friend, with three or four men of the same stamp, and after being refreshed, began the same conversation as hath been already mentioned. But in the height of their conversation, a company of soldiers surrounded the house, and by orders from the commander, seized Capt Hale in an instant. But denying his name, and the business he came upon, he was ordered to New York. But before he was carried far, several persons knew him and called him by name; upon this he was hanged as a spy, some say, without being brought before a court martial.”

The first reaction of many will, I think, be embarrassment for Hale. How could anyone on a secret mission be so gullible, or to use more generous terms, so naive or so credulous, to be taken in by a perfect stranger and then to disclose, the next day, the object of his mission to several more perfect strangers?

Thompson and O’Toole, the intelligence officers turned historians, would not have been surprised at Hale’s performance, as described by Tiffany, for they regarded Hale’s mission as fatally flawed from its inception. They offered a litany of criticisms of it. According to O’Toole, Hale was “completely ignorant of the espionage tradecraft and ill-suited for the job of agent. He was, first of all, not a man who could easily avoid attention, being above average height and bearing facial scars acquired in a gunpowder explosion. And he was a particularly bad choice for this mission because his cousin, Samuel Hale, was a Tory, General [William] Howe’s deputy commissary of prisoners, and at this very moment with Howe’s forces.” Furthermore, O’Toole added, the young captain’s superiors “arranged no cover story to account for Hale’s absence from the [Continental Army’s] Rangers, most of whom already knew what Hale was to do in any case. The possibility that the British might have their own spy in the American camp seems not to have occurred” to them.

Thompson expanded on the deficiencies besetting Hale’s mission: Hale “was given no secret ink, no code or cypher, nor was he given any training.” These experts would not, it would seem, quarrel with a description of Hale as a sacrificial lamb, dispatched on a mission doomed from the start. The “general reason for the failure of his mission,” writes O’Toole, “is obvious—it was a thoroughly amateurish undertaking in a business that permits few mistakes.”

If Hale, as described by Tiffany, acted in character by amateurishly conducting his mission, Rogers showed his colors in thwarting it. According to a fellow solder, Rogers was as “subtil & deep as hell itself.” A master of traps and ambushes during his military career and a man who had plotted and schemed for high stakes in London, Rogers would have had no trouble devising a ruse to snare the brave but artless young Connecticut Yankee. Notice how clever Rogers appears in Tiffany’s account. Realizing that to make his charges of espionage against Hale stick he needed corroborating testimony, Rogers evidently persuaded Hale that he could help him recruit a spy ring on the spot. The next day Rogers assembled a group of cronies posing as potential recruits, whom Hale regaled with details of his mission. With an abundance of supporting testimony now in hand, Rogers arrested the hapless Hale and sent him on his way to the gallows.


Since the American Revolution, the story of Nathan Hale has been the inspiration for heroic literature and popular illustration, as is seen in these two images.

Tiffany’s story does not reveal precisely how Hale came to Rogers’ attention. There are two possibilities. Rogers’ recruiting parties were combing western Long Island looking for soldiers, and their attention would naturally have been drawn to an athletic looking, unemployed young schoolmaster, which Hale was pretending to be. Alternatively, Hale may have been recognized by one of the crowd of Connecticut Tories who had crossed the Long Island Sound either to fight for the British or merely to escape the clutches of the new “rebel” government.

After Hale was executed on Sept. 22, his body was left hanging on the gallows, and word reached his relatives in Connecticut that several “deserters,” i.e. Connecticut Tories who had taken refuge in New York, recognized the corpse. Long Island swarmed with “deserters” who would have known Hale. Tiffany asserted that “several” Tories stepped forward to attest that they knew Hale and “called him by Name.” These multiple identifications would have clinched the case against Hale and may explain the summary nature of his execution on Sept. 22. There was absolutely no doubt about who he was and what he was up to.

We are now at the point of asking if Tiffany’s story is true. It is consistent with all that we know about Hale’s mission from “hard” contemporary evidence and from well attested tradition. We know that Hale, as Tiffany reports, was captured by Rogers. We know from Mackenzie that the capture took place on Long Island, as Tiffany reports. We know from the log of the British ship Halifax that Rogers and his recruiters were hovering off the coast of western Long Island from September 16 to 21, the period during which Hale must have been apprehended if he were to be transported to Manhattan for execution on Sept. 22. All the traditions about Hale’s execution assert that Tories played a conspicuous role in identifying or, as some charged, in betraying him: Tiffany’s account gives them their full due. Finally, Tiffany’s story is consistent with a Long Island tradition that Hale was captured in a local tavern.

Still, if Tiffany’s explosive story is true, why has it been buried in a single manuscript for more than 200 years?

It can be inferred from Tiffany’s manuscript that the story was circulating by word of mouth in Connecticut. Why did some version of it not find its way into contemporary newspapers?

The patriots, who controlled the press in revolutionary New England, would not have been receptive to a story that showed one of their own being outwitted by a Tory marauder. A Loyalist press did not exist until James Rivington revived his New York Royal Gazette in the fall of 1777. The more basic explanation of why nothing was published about Nathan Hale in 1776 is that he was not “news” at that time. The apotheosis of Hale occurred later, in the 19th century. As late as 1799 the historian of New England, Hannah Adams, lamented that Hale “has remained unnoticed, and it is scarcely known that such a character even existed.” In 1776 Tories would not have circulated an unflattering story to deflate Hale’s reputation because at that time he had none.

Was Consider Tiffany a person who would have trafficked in falsehoods or malicious rumors? The impression conveyed by reading his manuscript is that he was a stickler for the truth. He unsparingly denounced Benedict Arnold, a hero to most of his Tory contemporaries, because of his unscrupulousness and dishonesty, and he held the other characters who appeared in his manuscript to the highest moral standards. He does not appear to have been a retailer of lies concocted for partisan purposes.

Tiffany’s account of the capture of Nathan Hale fits the facts as we know them so well that one is tempted to accept it as being substantially true. Tiffany’s story reflects badly on Hale’s judgment but not on his moral virtue. His ineptitude as a spy does not diminish his patriotism; on the contrary, it gave him the opportunity, however hateful, to display it in its most magnificent dimensions.