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Abraham Woodhull hated his job. A humble farmer from Setauket, Long Island, he had made his peace with the British occupation of New York City in September 1776 and become a smuggler, running contraband to and fro across Long Island Sound. Now, however, in the early spring of 1779, he spent his time dodging around street corners and lurking about stinking wharves in downtown Manhattan. He had become a spy in the service of George Washington—and he didn’t like it one bit.

It might have been the money, or perhaps his lingering sense of patriotism. In any event, Woodhull had not demurred when a handsome young Continental Army major named Benjamin Tallmadge plucked him out of a Connecticut smugglers’ prison in August 1778 and suggested he take up work as one of Washington’s secret agents in New York City.

For several months the job had gone all right. Working from a busy Manhattan boarding house, Woodhull picked up a few hints and rumors and passed them to Tallmadge, who pronounced them valuable. In time, however, the walls closed in on him. Every glance seemed suspicious, every passing Redcoat on detail to arrest him. British officers took up residence next door, heightening Woodhull’s claustrophobia. His alias, Samuel Culper—which Tallmadge and Washington had thought up over a few glasses of claret—provided only flimsy cover. If detected, he had no escape route and could expect no mercy.

The moment came when Woodhull decided he must break away. The British were coming to get him. His life wasn’t worth a Continental dollar. He wanted out, back to his farm, anywhere but Manhattan.

On April 10, Woodhull sat down in his room to write a dispatch to Tallmadge. With each word, he trembled under the nagging conviction it might be his last. The tiny vial into which he dipped his pen only intensified his fear, for it contained a new and highly secret type of invisible ink. Tallmadge had told him not to let it fall into enemy hands—at all costs.

“Whenever I sit down,” Woodhull wrote, “I always feel and know my inability to write a good letter.” His peacetime calling had never prepared him for business such as this. Woodhull only prayed Washington would overlook his clumsy wording and appreciate he was doing his best to alleviate “the miserie [sic] of our distressed country.” After a few comments on British ship movements, Woodhull signed the letter simply “S.C.” and folded it, preparing to leave.

At that moment the door burst open, and figures charged into the room. Leaping from his chair, Woodhull knocked the vial of ink to the floor, and the precious liquid oozed away beneath his feet. He knew he was finished.

New York City teemed with spies in the spring of 1779. They had penetrated to every corner of the city. So far, however, they had accomplished little. Unskilled and largely uncoordinated, they bungled about like a bunch of schoolboys playing at war—and squabbled almost as much. Their “intelligence” often amounted to nothing more than rumor and gossip. When they did turn up something substantial, Washington feared with good reason the enemy had planted it.

Washington had long hectored his subordinates on the need for system and efficiency. Ad hoc espionage, he told them, risked lives for minimal gain. But his words had little effect. American generals and even some politicians hired their own spies for their own purposes, tossing them about like so many rag dolls and sometimes dropping them straight into the fire. This free-for-all practice intensely annoyed the commander in chief. It went against the grain of his belief in a highly centralized military organization.

Not until Tallmadge formed the Culper spy ring in August 1778 did Washington possess anything approaching an actual espionage network in New York City. And maintaining it was never easy. A 24-yearold Yale graduate from Brookhaven, Long Island, Tallmadge agreed with Washington that a small, dedicated group of spies—acting on a strict set of instructions under the commander in chief’s sole direction—stood the best chance of operating effectively in the city. To that end, Tallmadge recruited Woodhull, drilled him on his system of espionage and ordered him to set up shop in Manhattan alongside a number of junior informants and couriers.

Intelligence gathering has always entailed risk. A careless word, an overeager question or a clumsy step may mean death. Washington’s biggest problem, though, was not gaining accurate information, but getting it out of the city and into his hands. Detailed reports of enemy troop movements could only be submitted in writing—but how to get secret correspondence from a New York boardinghouse to his mobile army headquarters? Washington’s army had never completely sealed off the city from the countryside. Each day hundreds of civilians crossed on foot and by boat from British-held to American-held territory and vice versa. Sometimes spies could slip undetected among them. The British and Americans both vigilantly maintained patrols and checkpoints, however, and detained and searched anyone they pleased. Correspondence coming from either side was liable to be opened and carefully scrutinized.

Early in the war, American agents in New York had experimented with several methods of covert writing, including primitive ciphers and invisible ink. Posing as Loyalists, they composed innocuous letters to nonexistent family members in the hinterland and then penned sensitive information in milk or lime juice between the lines, hoping the British would unwittingly permit them through their pickets into American-held territory. Handlers in New Jersey then “roasted” the letters over flames to reveal the hidden message.

But the British quickly grew accustomed to this sort of trickery and captured many of Washington’s spies. Better means of eluding detection finally surfaced in November 1778, when Sir James Jay strode into Washington’s headquarters clutching a new and entirely foolproof recipe for invisible ink. A physician and amateur chemist who had been knighted by King George III, Jay spoke with a slight English accent and was insufferably pompous. His loyalty to the Patriot cause was unimpeachable, however, for his brother John stood as president of the Continental Congress. Washington, therefore, listened very carefully as Sir James expounded on how his ink could revolutionize the practice of military espionage.

The concept was simple. A spy would write his message on a plain piece of paper—packing paper, an envelope, a receipt or harmless piece of family correspondence—using Jay’s special ink. If the British became suspicious and roasted the paper over a fire, they would find nothing, for the ink was impervious to heat. To reveal the hidden words, the recipient had to apply a special chemical reagent, also concocted by Jay, who never shared his recipe.

Washington did not hesitate. Jay, he ordered, should be given every facility and financial assistance to manufacture his ink and its reagent. For his part, Jay insisted it be used only for high-priority intelligence and that every precaution be taken to ensure it never fell into enemy hands. He and Washington agreed to refer to it as “medicine” in all future correspondence.

Woodhull had followed these orders in destroying Jay’s secret ink at the moment of his discovery in the Manhattan boarding house. But his zeal was misplaced. The intruders were not British soldiers but a group of young ladies amusing themselves by roving about the building and surprising fellow tenants. Woodhull, gasping and incoherent, did not appreciate their joke; so they dismissed him as a ninny and flitted away down the hall. A few days later a gang of ruffians thrashed Woodhull and stole his purse, strengthening his resolve to leave the spy game for good. Tallmadge convinced him to keep at it and let him lie low a while.

The dangers had not passed. On July 2, a British cavalry force under Lt. Col. Banastre Tarleton—“butcher” Tarleton of later fame—launched a dawn raid against Tallmadge’s headquarters in Connecticut. Tallmadge eluded the raiders with the aid of militia, but much of his baggage fell into enemy hands. Disastrously, one of his stolen trunks contained a letter from Washington referring to a spy named “C____r” and a certain special liquid—Jay’s invisible ink. The letter also mentioned one “Higday” in New York, who had conveyed some of Woodhull’s correspondence. Receiving word of the attack, Washington ordered Tallmadge to protect Higday, but by then the British had already arrested the hapless junior operative.

Woodhull was by this point a nervous wreck, clearly unfit for active service. Anyway, Washington’s letter had compromised his cover. Tallmadge, therefore, agreed to let him move to the relative safety of Long Island, where he would act as handler for a new agent in the city. This new agent was Robert Townsend, a young, well-educated Long Island merchant who adopted the alias Samuel Culper Jr.

Moody and secretive, Townsend apparently suffered from manic depression. In some sense, as historian Alexander Rose has suggested, his decision to engage in espionage may have provided him an outlet to work through his melancholy. In any event, he made an excellent spy, and his efficiency and relative fearlessness allowed Tallmadge to resume operations in New York with nary a hitch.

Washington nevertheless refused to rely entirely—or even primarily—on the Culper ring to pro- vide him with intelligence from New York City. A prudent man, he understood the danger of putting all of one’s eggs in one basket. Washington also considered Tallmadge’s lines of communication dangerously exposed. From Manhattan, couriers carried Townsend’s reports about 55 miles east to Setauket. Boatmen under the supervision of Lieutenant Caleb Brewster then ferried them across Long Island Sound to Fairfield, Conn., where a dragoon picked them up and rode to command headquarters in either New York or New Jersey. The journey sometimes took days to complete, dating the information before it reached Washington’s hands.

Fortunately, many of Washington’s officers had risked his wrath to cultivate their own contacts in Manhattan, and by the spring and summer of 1779 some were providing excellent intelligence. Elijah Hunter, a 30-year-old former captain in the 4th New York Regiment, became a spy sometime around the Battle of Trenton. Since then he had operated in a series of private intelligence-gathering ventures under various officers. Sly and cagey, Hunter took to espionage as if born to it. Entering New York under the guise of a Tory bent on raising troops to fight for the king, he quickly worked his way into the inner sanctum of the British high command, gaining audiences with both commander in chief General Sir Henry Clinton and William Tryon, New York’s Tory governor.

The British also sensed Hunter’s aptitude for espionage—though they failed to discern his true political sympathies—and in March 1779, Clinton and Tryon suggested he work for them. Go to Philadelphia, they told him, pass yourself off as a Patriot and gain Washington’s confidence. Then report back to us. Hunter accepted their offer—along with the good solid coin they proffered as pay—and crossed the lines. Instead of spying on the Americans, however, he approached his handler, Maj. Gen. Alexander McDougall, and reported the whole scheme. McDougall, sensing an opportunity to employ Hunter as a double agent with unprecedented access to the British high command, sent him on to Washington’s headquarters in Middlebrook, N.J.

Washington didn’t trust Hunter—and he didn’t like double agents. “Their situation,” he told McDougall, “obliges them to trim a good deal in order to keep well with both sides; and the less they have it in their power to do us mischief, the better, especially if we consider that the enemy can purchase their fidelity at a higher price than we can.” Still, he resolved to give Hunter a try. After lecturing him on how persons who stood forth to help their country would never be forgotten, and how a good spy could provide more effective service than 500 soldiers in the field, the commander in chief sent Hunter back to New York to see what he learn about Clinton’s intentions.

Washington did not have long to wait. In mid-May, Hunter returned to Manhattan and entered almost immediately into a series of conferences with Tryon and Major John André, Clinton’s aide-de-camp. Their questions aroused Hunter’s suspicions. How many soldiers, they asked, garrisoned the Hudson River forts at West Point and Peekskill? Might a diversionary attack on Connecticut force the Patriots to divert troops away from those forts? Hurrying back to his lodgings, Hunter penned a letter to Washington and spirited it out of the city by unknown means. Expect, he warned, a “vigorous attack” up the Hudson.

Hunter was right. Nine days later, on May 30, Clinton launched a major attack upriver toward Kings Ferry, hoping to sever an important supply link to New England and possibly lure the Americans into a major battle on disadvantageous ground. Hunter’s warning enabled Washington to pull in his most vulnerable outposts and reinforce the critically important posts at West Point and Peekskill. Thus, although Clinton occupied Kings Ferry and surrounding points, he failed to gain anything more than a temporary advantage.

Hunter’s merit as an intelligence asset led Washington to expand his duties. Not long afterward he supplied the double agent with a false accounting of his army’s strength to feed the enemy. Yet the commander in chief never did wholly trust Hunter. “There are some little appearances about him that give me distrust,” he confided to one general. Hunter continued to provide useful and accurate intelligence, however, and his service taught Washington an important lesson. Order was important, but effective espionage made use of every resource available. Instead of trying to unite every intelligence outfit into one regimented organization under his direct control, Washington could utilize the existing, decentralized mode of operations.

While permitting his generals to recruit and handle their own spies, however, the commander in chief took an increasingly active role in overseeing their operations. Besides, he enjoyed the game of espionage with an almost childlike fancy and delighted in plotting the minutiae of cloak-and-dagger. In May 1779, in the swing of employing double agents, he sent Brig. Gen. William Maxwell, commander of the 2nd New Jersey Regiment, false reports on the Continental Army for an unidentified spy to pass along to the enemy. Copy out the reports, Washington instructed Maxwell, in bad handwriting and add spelling and grammatical errors in keeping with the spy’s cover as a semiliterate Tory farmer.

The false reports, purportedly from an intelligence-gathering mission among Continental troops, reveal Washington in an uncharacteristically impish mood. “I cant say theres much discontent among the sodgers,” he had the “Tory spy” report to his handlers, “tho’ their money is so bad. They get plenty of provisions and have got better cloes now than ever they had. They are very well off only for hatts. They give them a good deal of rum and whiskey, and this I suppose helps with the lies their officers are always telling them to keep up their spirits.”

Washington also kept a close eye on efforts by Tallmadge and others to develop increasingly complex ciphers and codes. Sir James Jay’s invisible ink had justified its earlier promise as a nearly infallible mode of secret communication. But there was never enough of it. For everyday correspondence—dispatches on military strength and deployments in particular—the development of some effective form of cipher was essential. Washington had already been burned several times over the course of the war when letters to or from his officers fell into enemy hands, and he had no desire to repeat the experience.

Tallmadge had used simple codes in prior correspondence with the Culper ring, as had Washington and some of his officers for particularly sensitive letters. For the most part, these amounted simply to a series of numbers representing a place or a name. In the summer of 1779, Tallmadge started work on a more comprehensive codebook, listing hundreds of words and their corresponding numerals, along with a key for individual letters and digits. The system was not terribly complex, but it sufficed, over time appearing both in Culper ring correspondence and letters written by Washington and his generals. The British apparently never broke it.

The Culper ring’s prominence and efficiency has led some historians to dub it the best—even the only— American espionage operation of the Revolutionary War. But the commander in chief employed a multitude of spies during the conflict, of every possible variety. Friendly Indians and ragtag frontiersmen roamed the woods to gather intelligence on enemy activities in Canada and the Midwest. Civilians—including women, farmers and nondescript tradesmen—crossed British lines, sold food and other goods and then reported back to Washington about enemy dispositions. In New York and other British-occupied territories, doctors, prisoners on parole, merchants, boatmen, prostitutes and others garnered intelligence or simply smuggled newspapers. Washington also exploited flags of truce and employed other dubious methods to gather information when it suited his purposes. Some say his agents started the fires that burned much of New York City just after the British occupied it in September 1776.

Washington was an idealist who passionately believed in the cause for which he fought. In striving to attain victory, however, he was pragmatic. The end did not justify any means—he rejected torture, for example—but it did a lot of them. In October 1778, for example, Washington wrote Presbyterian preacher Alexander McWhorter about two condemned prisoners to whom he was ministering. The prisoners, John Blair and David Farnsworth, had just been convicted of counterfeiting Continental currency and spying for the enemy, and McWhorter, like any good preacher, was busy preparing them for their journey to the afterworld. Yet Washington asked him to squeeze them for information. “Besides the humanity of affording them the benefit of your profession,” the commander in chief wrote, “it may in the conduct of a man of sense answer another valuable purpose—and while it serves to prepare them for the other world, it will naturally lead to the intelligence we want in your inquiries into the condition of their spiritual concerns.” Whether McWhorter got the prisoners to talk before their November execution remains unknown.

This willingness to bend the rules when necessary enabled Washington to embrace the entire crazy-quilt fabric of Revolution-era espionage. Few methods of procuring information, however shady, stood above his purview so long as they provided him the tools necessary to beat the enemy. At the same time, Washington worked closely with such handlers as Tallmadge and even met with individual spies to ensure they efficiently carried out their work. No detail was too small to escape his attention.

By 1779 America’s diverse and growing intelligence-gathering network had outstripped its awkward beginnings to become a remarkably effective tool. Washington’s spies supplied him with astonishingly accurate accounts of British troop dispositions and movements, including the identities of individual regiments; the size, layout and armaments of fortifications big and small; and the movements of British, Hessian and Loyalist officers. When Clinton left Manhattan for anywhere, even nearby Long Island, Washington learned of it almost immediately. He heard of rumored tensions between the British army in New York and politicians in London, and sought and received specific information on the prices of clothing and provisions, troop morale and everything else imaginable. Washington also received minute accounts of British, Loyalist and Indian troop strengths and fortifications in Canada and along the western frontier.

By war’s end in 1783, American spies had advanced their craft almost to European standards. Formation of the Central Intelligence Agency remained on the far horizon. But George Washington had become America’s first spymaster in chief.

For further reading, Edward G. Lengel recommends: Washington’s Spies: The Story of America’s First Spy Ring, by Alexander Rose, and Turncoats, Traitors and Heroes, by John Bakeless.

Originally published in the July 2009 issue of Military History.