Nathan Hale's Mission

2 JULY 96


The ironies of success and failure


Streeter Bass

"How beautiful is death when earned by virtue.
... What pity it is
That we can die but once to serve our country."

Joseph Addison, Cato

One of the ironies of the world of clandestine activity lies in the fact that almost all of its popular heroes are the ones who were caught. Ironic, perhaps, but obvious — inasmuch as, if you aren't caught, chances are no one will ever hear of you. For every 10,000 Americans to whom Nathan Hale and John Andr6 are familiar names from grammar school on, there is hardly one who has ever heard of Abraham Woodhull or Robert Townsend or Edward Bancroft.

In the 20th century the concept of the spy, while still retaining a hefty amount of its traditional pejorative content, has acquired a certain glamor which it didn't have in the 18th and 19th — enough, in fact, to encourage an appalling amount of amateur and semi-professional activity performed in sufficiently inappropriate contexts and with sufficient clumsiness to ensure a plethora of embarrassing failures. By the criterion of failure mentioned above, we ought thus to have, at the present time, a bagful of heroes. That we don't is confirmatory of the basic dictum of ends justifying means — whether you wind up a hero or a villain in espionage (providing, of course, you get caught) depends largely on public agreement regarding the desirability of the ends. If, by popular agreement, the ends to be served by the spy's mission are "patriotic," he is a hero; if they aren't, he isn't.

By the Fourth of July, 1776, the colonies had been at war with the Mother Country for more than a year. Until then, things hadn't gone too badly. The Redcoats had been ignominiously chased back from Concord and shut up in Boston. The pyrrhic victory of Bunker Hill had gained them precisely nothing. Howe — by neglecting to occupy Dorchester Heights — had committed the first of a series of blunders which went far toward assuring the eventual success of the Revolution and had betaken himself to Halifax to re-fit and await further orders.

To Washington in Cambridge, commanding an army which proudly referred to itself as "Continental," it seemed clear that when the British returned it wouldn't be to Boston. By now it would be patently obvious to King and Cabinet that they were going to have to put down rebellion in all thirteen colonies; it was no longer to be simply a question of reducing one obstreperous New England town. Plainly the British would attempt to establish a beachhead and a base of operations from which they could undertake to invest the entire eastern seaboard.

There was little doubt in Washington's mind where this attempt would be made. New York had a harbor which could shelter the entire Royal Navy. It was the key to the Hudson-Champlain highway to (and from) Canada which, once occupied and secured, would cut New England off and split the colonies. The city was large enough to supply winter quarters for a sizable force and was already known for a heavy ballast of Tory sympathy. So sure was Washington of all this that as early as January, he had allowed General Charles Lee to go to New York to begin organizing its defenses. And the day after Howe's evacuation of Boston, the first Continental units left Cambridge for Manhattan.

Throughout the spring and early summer Washington's army worked feverishly to make the city defensible. It wasn't an easy job, and Washington would have preferred not to have to try. But he had his orders; Congress wanted New York held at all costs. Batteries, entrenchments, strong points were dug and constructed at key points on the island by an army only too painfully aware that both the Hudson and East Rivers were deep enough for the largest ships-of-the-line and equally aware of its own acute shortage of artillery. As Dorchester Heights commanded Boston, so Brooklyn Heights dominated New York, and General Washington, not wanting to repeat Howe's mistake, occupied and fortified the position as best he could. Then he and his army waited for Howe's return.

At the beginning of July, the British came back, and — as Washington had guessed — they came back to New York. Cornwallis and Clinton sailed in from their unsuccessful attempt against Charleston, South Carolina. Sir Billy Howe, his troops rested, re-equipped, and reinforced, pulled in from Halifax, and his sea-going brother, Admiral Lord Howe, arrived from England with a large naval force and transports crammed with thousands of British troops and German mercenaries. Howe landed his forces on Staten Island and began, in his usual leisurely way, to prepare an assault on the city. The Continental Army on Manhattan peered at the forest of masts in the Narrows and speculated on its ability to deal with one of the largest overseas expeditionary forces in Europe's history. They wondered where and when Howe would strike.

Howe was in no hurry, and the "when" didn't become apparent for another month. The "where" turned out to be Long Island. On the moming of 27 August, Howe loaded his troops into boats and moved them across the Narrows to Gravesend Bay. General Israel Putnam, a fierce fighter but a bad tactician, deployed his forces to meet him, unfortunately leaving his left flank unguarded. Howe hit him precisely there, turned his flank, collapsed his line, routed his force, and committed the second blunder which helped lose England her colonies. With the Americans fleeing pell-mell across the Gowanus marshes toward Brooklyn, Howe called off the pursuit which, had he let it go on, would have destroyed the Continental Army and ended the war. A two-day nor'easter then blew up, preventing the British fleet from entering the East River, and Washington, in a brilliant night-time Dunkirk, evacuated the remnants of his battered army to Manhattan.

Realizing the impossibility of holding New York, Washington proposed to Congress that he be allowed to burn the town and retire to the mainland rather than risk being trapped on Manhattan island. While he waited for an answer, he took under consideration and intelligence problem of the first magnitude: What were Howe's intentions? He didn't worry about his capabilities; it was all too evident that Howe had the capacity to do just about anything he wanted. His brother's fleet controlled the rivers, his own army — well-trained and equipped — outnumbered the Americans (since their losses on the 27th) by more than two to one. But what did he intend to do? Would he move north, cross into Westchester, and cut off the whole island? Would he move against some point mid-way up the island and throw a cordon across to the Hudson, thereby trapping the Americans in the town? Would he perhaps make an assault directly on the town itself?

In vain Washington canvassed all his available sources. He sent General Clinton with 100 men on a raid across Long Island Sound from New Rochelle to round up a few Tories who might be able to tell him what the British seemed to be doing. But British naval patrols intercepted the raiders and prevented their landing. There seemed to be only one other way to get the information be needed. He called in Lieutenant Colonel Thomas Knowlton, commander of his newly organized Ranger Regiment and asked him to canvass his officers and come up with a volunteer for an espionage mission to Long Island.

Among Knowlton's company commanders was a young captain from Connecticut — 21 years old — who had just transferred into the new regiment. His name was Nathan Hale; he had graduated from Yale with the class of '73, bad taught school for some 18 months, and had sat out the siege of Boston as a captain in Colonel Webb's 19th Connecticut Foot. Hale was an intensely idealistic young man, seized with a burning ardor for independence, and filled with an almost overwhelming desire to perform a signal service for his country.

It had been no help to these inner drives of his to be forced to endure eight months of inactivity in Cambridge. The crowning ignominy for a young officer aching to lead his troops in combat had been the assignment of Webb's regiment to remain in reserve in New York during the Battle of Long Island. Following the initial debacle, Colonel Webb's Nineteenth was ordered across the East River to support the disorganized and demoralized troops now trying to bold a small perimeter in Brooklyn. It took its place in the line the evening of the 27th but — without firing a shot — was ordered back out again two days later with the evacuation to Manhattan the night of the 29th.

When, therefore, a couple of days later, Hale was offered a place in Knowlton's Rangers — a new organization calling itself "Congress's Own" and intended as a small, elite reconnaissance outfit — he jumped at the chance, hoping that such an assignment would give him the opportunity he craved, to see some action. That it would have if he hadn't gone on his espionage mission, is one of the ironies of his short and tragic story.

Knowlton assembled his officers the morning of Tuesday 10 September, briefed them on the situation, and asked for volunteers. In response he got a large measure of dead silence. Finally Lieutenant James Sprague, a veteran of the French and Indian War, voiced the thoughts of his brother officers:

"I'm willing to fight the British and, if need be, die a soldiers death in battle, but as for going among them in disguise and being taken and hung up like a dog, I'll not do it."

Knowlton made another appeal, got no response, and dismissed the meeting.

Hale was upset. In his idealism, he too felt the role of spy to be a disgraceful one. But, offensive or not, here was the chance to serve he'd been waiting for. Wanting to talk it over with someone, be sought out his Yale classmate, Captain William Hull. Years later Hull recorded the conversation in his memoirs.

Sensing that Hale was about to volunteer, Hull tried to dissuade him. He pointed out the essentially dishonorable nature of the job and the ignominious and inevitable fate if he got caught. Hale's famous words on the gallows are familiar to everyone, but what he said to Hull is perhaps somewhat more interesting:

"I wish to be useful," Hull reported him as saying, "and every kind of service, necessary to the public good, becomes honorable by being necessary." Then he went on, "If the exigencies of my country demand a peculiar service, its claims to perform that service are imperious."

Hale went back to Knowlton and volunteered for the assignment.

The details of the mission are maddeningly meager. What is known with reasonable certainty is only that he and his company first sergeant, Stephen Hempstead, left New York by land on or about 12 September, went out the Connecticut shore as far as Norwalk, were then set across the Sound by a Captain Pond in the sloop Schuyler during the night of 15-16 September, and that Hale went ashore at Huntington, Long Island, while Hempstead returned to Norwalk with instructions to wait there either until Hale returned or until he received other word from him. Hempstead also reported that Hale adopted as cover the role of a Tory schoolmaster seeking refuge from Connecticut and looking for a job on Long Island. He was dressed in a civilian suit of "Holland brown" cloth, wore a round broad-brimmed hat, and carried his own Yale diploma to establish his bona fides as a qualified teacher. This also meant, of course, that he was using his true name. Hempstead also remembered that Hale took off his silver shoe buckles and left them with him stating that they would not "comport with his supposed calling."

And that is all that is known of Hale's mission from the morning of 16 September until the night of the 21st when, according to General Howe's daybook for 22 September:

"A spy from the Enemy (by his own full confession) apprehended last night, was this day Executed at 11 o'Clock in front of the Artillery Park."

As Hale and Hempstead moved up the Connecticut shore looking for a boat to take them across the Sound, events were taking shape behind them which were going to alter the mission drastically. On the morning they left New York, Thursday the 12th, Washington got his answer back from Congress. The lawmakers in Philadelphia ordered him not to burn the town since it "... could undoubtedly be recovered even should the enemy obtain possession for a time." The question of evacuating the city, however, they left to Washington's own discretion, and he immediately ordered a withdrawal to the upper end of the island to begin the following day — Friday the 13th. His intention was to occupy Harlem Heights and await Howe's next move. By Sunday morning, the 15th, more than half the army was dug in on the heights but, of the rest, some 3,500 were still doing rearguard jobs in New York and the remainder were strung out in a long thin line along the East River protecting the evacuation route.

At seven a.m., Howe's intentions suddenly became clear. Under cover of a heavy naval bombardment, he moved a large body of light infantry and Hessian grenadiers across the East River and landed them at Kip's Bay, now the foot of 34th Street. The defending Americans, still unnerved from the debacle of the week before and unused to the kind of heavy cannonading they were getting from the British frigates, broke and ran even before the assault wave hit the beach. Not even Washington's personal presence was able to stem the retreat and by noon Sir Billy and his staff were able to come ashore.

Howe then proceeded to make the third blunder in the series which saved the Revolution. There were still 3,500 Continental soldiers in Lower Manhattan who could easily have been cut off. But Howe, a leisurely and methodical man, felt that he needed to secure and organize his beach-head before sending his troops across the island to seal it off. Having given the appropriate orders for this, he, General Sir Henry Clinton, and Loyalist Governor Tryon repaired to the Murray mansion on Murray Hill and relaxed with cakes and claret and the charming Mrs. Murray.

With the British high command thus pleasantly occupied, General Putnam led the remaining 3,500 Continentals up the west side of the island and, in the nick of time, got them out of danger. The following day, at the moment Hale was landing on Long Island, his regiment, Knowlton's Rangers, was spearheading a pre-dawn raid on Howe's northern outposts which developed into the Battle of Harlem Heights. Knowlton was killed in the engagement but the day was successful for the demoralized Americans, giving them their first look since Bunker Hill at the backs of the Redcoats.

It would be hard to imagine a situation more ironic than Hate's had now become. Wanting more than anything else to take his men into battle, he had opted instead to undertake a mission both dangerous and distasteful to him. On the day he left Norwalk to cross the Sound, Howe's attack erased the question he'd been sent out to answer. The day he landed on Long Island saw his regiment distinguish itself in the action he longed to participate in. Unhappily unaware of all these things, however, Hale set off on his mission.

How he spent the next six days can only be a subject for speculation and, over the years, many people have speculated over many pages. There are all sorts of stories, rumors, conjectures, and local myths concerning where he went, what he did, where he was captured, even where the artillery park was located in front of which he was hanged.


Hales earliest biographer, Isaac Stuart, for example, writing in 1856 and relying on local Long Island tradition, has Hale making his way to Brooklyn, across to New York, and then all the way back again to Huntington, where he was captured because he mistook a British patrol boat for one coming to pick him up. This is hardly likely. It calls for a lot of travelling for only six days, and the distance from Huntington to New York makes it improbable that, having been taken the night of the 21st, be could have been returned to New York in time to be executed at 11 a.m. on the 22nd. Other versions have him hailing a boat from the British brig Halifax from the east shore of Manhattan under the impression it was friendly; or crossing the East River and being picked up in Flushing by Lt. Colonel Robert Rogers, the turn-coat commander of the Loyalist "Queen's Rangers;" or — by far the most likely — being taken while trying to pass the British picket guards less than a mile and a half from his own troops. Some versions also include the statement that he was recognized and denounced by his cousin Samuel Hale of Portsmouth, New Hampshire, a staunch Loyalist who was with Howe's army as a deputy commissary of prisoners.

Probably the best job of reconstructing Hale's movements is that done by Corey Ford,* who brought to the task not only the results of an exceedingly painstaking and thorough piece of research, but also a large measure of firsthand experience with the realities of espionage deriving from his service with OSS.

Ford speculates that Hale, after landing at Huntington, must very soon have learned of Howe's occupation of New York and recognized the essential uselessness of continuing the mission on Long Island. He would have realized, thinks Ford, that if anything was to be gleaned from the mission, he would have to go into New York to get it. The Brooklyn ferry would be closely controlled, but Loyalist provision boats went daily from Long Island ports to supply the troops in the city. Ford has him going as a crew member on one of these boats from Oyster Bay to New York. Once there, he would have moved cautiously from one British installation to another, listened to coffee-house gossip, made notes and sketches, and in general done what a careful and conscientious agent is supposed to do.

On the night of the 20th, however, an event took place which made his eventual capture almost inevitable. The city caught fire and a third of it was totally destroyed. What Congress had expressly forbidden Washington to do bad now happened anyway, and the General, watching the red sky from the balcony of the Morris Mansion on Harlem Heights, remarked to his aide, Tench Tilghman, "Providence, or some good honest fellow, has done more for us than we were disposed to do for ourselves."

The fire seems to have started accidentally, but there is no doubt that many a "good honest fellow" of Patriot persuasion played arsonist and contributed materially to its getting out of control. Enraged British soldiers and Loyalist citizens, trying desperately to cope %vith the conflagration, did in fact catch several of them in the act and either bayoneted them on the spot or threw them into the flames. Obviously security would be greatly tightened in the wake of this disaster and extensive attempts made to round up the guilty. Stringent measures would be taken to keep civilians from leaving the city, especially northward toward the American lines. It would seem obvious that Hale's chances of getting through the lines would now be greatly worsened, and equally obvious that he must in fact have been picked up while trying to work his way up to Harlem.

In reconstructing Hale's capture, Ford also brings in the Tory cousin. He conjectures that Hale, caught by the picket guard, was brought first to General Robertson, one of Howe's brigade commanders, to whom he gave his cover story and showed his Yale diploma. Robertson, struck by the similarity of name with that of the deputy commissary of prisoners, sent for Samuel who identified his cousin, by a birthmark, as Nathan Hale of Coventry, Connecticut, Captain in the Continental Army. Hale was thereupon stripped and searched, his notes and sketches found in his shoes, and the jig was up. He then freely admitted to his identity and his mission and it remained only to inform the British commander-in-chief of the capture and request orders as to the disposition of the case.

Howe's headquarters were at the Beekman Mansion, an elegant country estate overlooking the East River at what is now 51st Street and First Avenue.

Thither Hale was led and the situation explained to the General, who, without the formality of a trial, ordered the prisoner remanded to the Provost Marshal to be hanged the next morning. He was then placed for the night under guard in the greenhouse on the Beekman estate.

On the evening of the 22nd a flag of truce approached the American lines. Washington dispatched his Adjutant Ceneral, Colonel Reed, to meet it, ac. companied by Major General Putnam and Captain Alexander Hamilton. The officer accompanying the flag identified himself as Captain John Montresor, Chief Engineer of His Majesty's Forces in North America and Aide-de-Camp to General Howe. The official purpose of the flag was to convey to General Washington, General Howe's protest of an illegal and inhumane weapon — a cut-off nail inserted in a musket ball — several of which had been found in abandoned American quarters in New York. Orally, however, and in addition to the official written communication, Montresor told Reed that a Captain Hale had been arrested the previous night within the British lines and had been executed as a spy that morning.

Later that night William Hull got from Hamilton the news of his classmate's fate. He went immediately to Tilghman, asked and was given permission to accompany the flag by which Washington's answer would be delivered on the 24th. Washington's official message made no mention of Hale or of the fire. It merely apologized for the "wicked and infamous weapon. Hull, however, found opportunity for a few words with Montresor about the fate of his friend and classmate. In his memoirs he recalled the conversation in some detail:

I learned the melancholy particulars from this officer, who was present at the execution, and seemed touched by the circumstances attending it. He said that Captain Hale had passed through their army, both of Long Island and York Island. That he had procured sketches of the fortifications, and made memoranda of their number and different positions. When apprehended, he was taken before Sir William Howe, and these papers, found concealed about his person, betrayed his intentions. He at once declared his name, his rank in the American army, and his object in coming within the British lines.

Sir William Howe, without the form of a trial, gave orders for his execution the following morning. He was placed in the custody of the Provost Marshal, who was a Refugee [Loyalist], and hardened to human suffering and every softening sentiment of the heart. Captain Hale, alone, without sympathy or support, save that from above, on the near approach of death asked for a clergyman to attend him. It was refused. He then requested a Bible; that too was refused by his inhuman jailer.

"On the morning of his execution," continued the officer, "my station was near the fatal spot, and I requested the Provost Marshal to permit the prisoner to sit in my marquee, while he was making the necessary arrangements. Captain Hale entered: be was calm and bore himself with gentle dignity, in the consciousness of rectitude and high intentions. He asked for writing materials, which I furnished him: he wrote two letters, one to his mother* and one to a brother officer." He was shortly after summoned to the gallows. But a few persons were around him, yet his characteristic dying words were remembered. He said "I only regret that I have but one life to lose for my country."

Thus ended a story of little significance in the annals of war. An agent dispatched on what turned out to be a useless errand, caught partly because of insufficient preparation and only elementary attention to cover, partly because of circumstances beyond his control, immediately and unceremoniously executed, and buried in a forgotten grave — on the whole a series of events quite unlikely, on the face of it, to provide the material for making a patriotic legend or a national hero. But such is the power of the word — a garbled quotation from Addison, spoken by a condemned man on the gallows — that one quick sentence spoken in precisely the right circumstances can illuminate in one brilliant flash a whole landscape of human motivation. Hale is what he is in the American pantheon not because of what he did, but because of why he did it. From the early 19th Century on, the chroniclers of Hale have been tireless in their recital of this fact. To a man they have insisted on contrasting Hale and Andre — the one universally admired and pitied by both sides, eulogized and ultimatedly re-buried in Westminster Abby; the other buried unnoted except by his family and friends and almost forgotten until many years later. Their judgments of the two men are invariably made on the basis of the motivation shown by their 'last words; Andre concerned only with his personal reputation: "I beg the gentlemen to bear witness that I die as a soldier," Hale concerned that he could no longer serve his country's cause.

Perhaps the final irony in Hale's story is that the fact that we know it at all is due solely to the presence at his execution of one British officer who was sufficiently sensitive to his demeanor and impressed by the character of his motivation to have befriended him, to have heard what he said on the gallows, and to have passed it on to his friends.

[Top of page]



* Ford: A Peculiar Service (Little Brown, Boston/Toronto, 1985).

* Hull — or Montresor — slipped here. Hales mother had been dead for years. The letters were to his brother Enoch and to Colonel Knowlton. He didn't know that Knowlton had been killed on the 16th.

[Top of page]



Historical Document
Posted: May 08, 2007 08:41 AM
Last Updated: Aug 04, 2011 01:09 PM