DEDICATION

The execution of Nathan Hale on September 22, 1776, was the lowest point in a month of low points for General George Washington. First, the British had taken New York City and Long Island�the cornerstones of Washington�s strategy because of their valuable geographic and economic positions at the heart of the North American colonies. Now, Washington�s attempt at building an intelligence network to recoup that loss had failed spectacularly. Just two months after the fledgling country�s declaration of independence, there seemed to be no future for the new nation.

And yet there had been so much hope just a season ago, in spring. After successfully sending the British packing from Boston in March after a prolonged siege, Washington had begun ordering troops toward New York City, whose harbor was of tremendous tactical�and psychological�importance. If the Patriots could hold that other great port of the Northeast, victory might be within reach.

As Washington left Massachusetts on April 4, 1776, to begin his own march southward to rejoin his men, the cheerful reports sent back by the advance parties were confirmed: Farmers and tradesmen were greeting the American troops as they passed through rural villages, pressing gifts of food and drink on the soldiers who had displayed such courage and pluck fighting the redcoats.

�Enjoy this bacon,� urged local butchers, heaving slabs of salted meat onto the supply wagons.

�Fresh milk!� announced the housewives who scrambled out of their cottages wielding buckets and dippers.

Gaggles of little boys wearing homespun blue jackets gathered to parade in front of the men as they traversed through town�one child held up a twig as if playing a fife; another pretended to beat a drum in a marching rhythm; the rest chanted the popular refrain �Join or die!� as they reveled in the Patriotic fervor and holiday atmosphere.

Even the sophisticated city crowd, usually much more reserved in their displays of celebration than the country folk, had cheered in the streets as Washington crossed into Providence, Rhode Island. In roadside taverns and stylish urban coffeehouses across Connecticut, toasts were raised to the unlikely homegrown heroes and their quiet but imposing leader. As word spread up the Hudson Valley that the Continental Army was on the move, settlers who now considered themselves Americans, rather than Dutch or German or British subjects, had whispered prayers for the protection and advancement of the cause of independence.

Throughout his nine-day journey spanning four states and nearly three hundred miles of forest roads soggy with springtime mud, Washington had seen increasing hope among the people. There were dissenting voices�those whose closed shutters and drawn shades as the Continental Army passed bespoke their loyalty to King George III and the motherland. But it was clear that there was a sense of growing excitement that this wild, untested experiment in personal freedom and individual rights just might prove more powerful than the most disciplined and well-equipped fighting force on earth.

Despite the buoyant spirits of the people, Washington�s own hope was kept in check by a sober view of facts. While the Patriots had enjoyed some early victories in Massachusetts, these wins came at a high cost when compared with their tactical significance. The Battle of Bunker Hill in June 1775, however, had gone to the British, though with heavy loss of life and limb on both sides. The Siege of Boston, which ended the following March, had been a win for the Patriots, but their success was due more to the position and strength of the American fortifications than any great offensive maneuvers to rout the enemy. In the end, the British gave up on the city, leaving voluntarily rather than fleeing in an all-out retreat. General William Howe, commander in chief of the British army in North America, had his sights set on a much bigger and more agreeable prize than belligerent Boston.

New York, tenuously held by a few American troops, was desired by both sides. In the north, the Americans had secured Boston for the moment. To the south, the action had not yet reached a critical point, though its time was coming. Right now, the most pressing concern was in the middle states, where Philadelphia and New York lay vulnerable. Philadelphia was the largest city in the colonies at the time and held great symbolic status as a seat of innovation, boasting one of the first hospitals and public libraries, as well as hosting the meetings of the Continental Congress. Capturing the seat of the fledgling nation�s government would be a great victory for the British. And New York City was the linchpin�if the British won it they could bring the colonies to their knees.

As the second-most-populous city in the colonies, New York was their northern economic hub. But even more significant was New York�s location and situation�right in the center of Britain�s North American settlements and home to both a large deep-water harbor and access to the Hudson River. The army that held New York City and its waterways had a strategic advantage not only in controlling the import and export of foodstuffs and dry goods (which, in turn, affected the economic stability of the region) but also in securing a key foothold for transporting troops up and down the coast.

Maintaining control of New York would give the American fighting corps and the colonial populace a tremendous boost in confidence. Failing to capture and hold New York City and New York Harbor would certainly be an embarrassment to the British army and navy, but they would survive the blow. For the Americans, however, losing the region would be a tragedy, destroying morale, cutting off trade, and drastically lowering the odds that the Patriots would win the war.

New York�s strategic significance, from a trade perspective, was not lost on General Howe. The loss in Massachusetts was a disappointment, but Boston was not the ultimate prize for the British. Howe wanted to choke off the Revolution by isolating the northern colonies from the southern ones. If the political radicals in the somewhat geographically clustered northern cities were segregated from their counterparts in the more spread-out south, they could not cross-pollinate ideologies, and the various factions might be more easily eliminated. It was a classic case of divide and conquer, with New York City as the essential element in creating the chasm.

After regrouping in Halifax, Nova Scotia, following their defeat in Boston, the British set out for New York. On June 29, 1776, three British ships sailed into lower New York Harbor, with General Howe aboard one of them. Both sides knew a battle was imminent.

As Washington marched south in anticipation of Howe�s attack, he must have nursed the hope that the Continental Army�s muscle and moxie were enough to outfight the British and hold Manhattan. Being a seasoned fighter and a brilliant strategist, he would have understood, perhaps better than anyone else in North America at the time, that control of New York City was essential for the cause of liberty�and that keeping the city would be a daunting task.

Washington and his men arrived in New York in mid-April 1776 and settled in Manhattan. That summer news arrived that both cheered and sobered them. Fifty-six delegates had convened in the midst of stifling July heat in Philadelphia to form the Second Continental Congress, and had forged the Declaration of Independence. If ever there was a point of no return, this was it.

Knowing the attack on New York would not be long delayed, Washington made a short trip to New Jersey and Pennsylvania to meet with his generals. They discussed New York�s defenses and supplies�all while trying to anticipate the exact mode of attack. The British, meanwhile, began amassing troops on undefended Staten Island in advance of storming the American positions just across the water in Brooklyn and Manhattan.

As August dragged on, tensions mounted. A copy of the July fourth declaration had been put before the Crown, which meant that King George finally understood the seriousness of the colonists� determination to fight. No longer would King George order his generals to show restraint in their efforts to squelch the rebels or maintain that a mere show of force would be enough to subdue the Revolution. He would not hold back. He would not show mercy. Of this Washington felt sure, and the weight of the �lives, fortunes, and sacred honor� pledged in the name of freedom rested heavily upon his shoulders.

Across the river from Washington, General Henry Clinton had arrived to help lead the attack upon the American positions in New York. As August waned, the British ships loomed large in the harbor, the growing number of redcoats on Staten Island intimidating the sparse American troops.

Faced with an impending attack, Washington sighed one August day as he surveyed the undisciplined, ragtag army at his command in lower Manhattan; his aide-de-camp shifted nervously behind him. The general cleared his throat. �General Howe is rumored to have more than thirty thousand men in the Royal Navy assembled offshore, and twenty thousand men amassed on Staten Island. And we have�.�.�.�?�

His aide was reluctant to reply: �Ten thousand.�

If the number was a blow to Washington, he did not show it. Ever the stoic, he refused to allow this dismal news to throw him into despair. Washington was famed as a man who never lost his nerve in battle. The sound of musket fire, the crash of cannonballs, the smell of smoke�none of that seemed to shake his calm, measured way of surveying the chaos and keeping his wits about him as he led his men forward.

But despite Washington�s steely nerve, the Americans were in grave trouble. Even substantial numbers of troops meant little without proper training and equipment, and Washington�s men lacked both. Washington had the utmost confidence in his officers, but to say that the rank and file of the Continental Army was rough around the edges was an understatement. City men who had never before wielded a rifle stood with country folk who had never had a day of formal schooling. Hardy homesteaders struggled to cooperate with young men of landed wealth who had never known a moment of discomfort or hunger in their lives. Old men lined up with boys who had lied about their age to join the rebels in pursuit of adventure. They came from all over the country: from as far north as the mountains of New Hampshire and as far south as the swamps of Georgia. Many of Washington�s men had never before been more than fifty miles from the place of their birth, let alone met anyone with such a strange accent as could be found in the hills of Virginia or the Puritan settlements of Massachusetts. They were all on the side of liberty, but there the unity ended.

Most were brave, to be sure, and loyal�perhaps to a fault. And they were all passionate about their liberty. Washington knew he had the hearts of his men, but whether the passion of an undisciplined few could hold New York against the meticulously trained British forces was another question.

�Hang together or we all hang separately,� Washington mused, reciting one of the familiar mantras of the Patriot cause, as he caught a few strains of a bawdy pub song led by the Marylanders sitting around a campfire. All possible preparations against the British onslaught had been made, and he and his men would have to trust it would be enough.

Knowing that an attack was imminent, Washington had made the strategic decision to divide his men into five groups. One had already crossed the harbor to Long Island, and another was stationed in northern Manhattan to fend off a British encroachment from that direction. The other three groups were situated to defend the lower end of Manhattan. There were several land routes the British might take, but Washington felt confident that all but the least likely and somewhat untraveled route, through Jamaica Pass, were secure. And now�.�.�. they waited.

As if the loss of most of New York weren�t bad enough, Washington�s autumn was about to get worse. While the defeat at the Battle of Brooklyn had been a blow, the retreat had gone better than planned. Washington�s next endeavor would not be so fortunate, ending instead in disaster.

The few American troops still holding Manhattan were hanging on by a thread, and Washington was desperate to strengthen their position. To do so, he would need a spy to collect information on British plans. Espionage was not a new activity to Washington. Having fought in the French and Indian War and served as a spy himself, he understood the roots of the present conflict�an insight that would frame his use of an intelligence network in the Revolution.

In February 1777, Washington wrote to Nathaniel Sackett, a New York merchant, supplier to the Continental Army, and Patriot activist. The short letter got to the heart of the matter immediately. He offered Sackett fifty dollars a month�a generous sum from the cash-strapped American government�to establish a network of spies to learn �the earliest and best intelligence of the designs of the enemy.� Sackett�s efforts, while initially fruitful, collapsed a few months later in a series of unfortunate mishaps and failed missions that yielded few results of the impact Washington was seeking. Finding the right man to lead the New York ring was proving harder than planned.

In the fall of 1777, a year after Nathan Hale�s death, Washington still had no New York spy ring, mostly because the general�s attentions were diverted again from New York to Philadelphia, which the British had recently captured. For the next few months, Washington devoted most of his attention to regaining the City of Brotherly Love and placed the New York intelligence efforts on hold indefinitely.

Growing up, Abraham Woodhull had been a neighbor of Tallmadge�s, and he shared many of the young officer�s ideals, but that�s where their resemblance ended. By all accounts, Woodhull was no bright-eyed, optimistic, jolly-young-man-turned-soldier who ran eagerly into the welcoming arms of the American cause. His sentiments lay with liberty, but as a confirmed bachelor and self-proclaimed old man before the age of thirty, he put such a premium on personal autonomy that he avoided official military service, where he would have been subject to the orders of superiors.

Abraham was his parents� third son, raised under the shadow of a prominent and celebrated family (which included the ill-fated General Nathan Woodhull, a cousin) to be neither the heir nor the spare to the paternal estate. While his older brothers, Richard V and Adam, were groomed to step into the role of American gentlemen, young Abraham was released to the freedom of the outdoors. It was a dismissal he neither minded nor resented, as he found the tedium of schoolwork uninspiring. While his brothers were laboring over passages of classical rhetoric, Abraham gained an intimate knowledge of the landscape of Long Island, connecting every topographical feature with its owner.

The Woodhull girls, Susannah and Mary, doted on their baby brother, and Abraham was equally fond of them. When Mary married Amos Underhill and moved with him to Manhattan, Abraham made a habit of visiting them. Sometimes he traversed Long Island and then crossed the East River to Manhattan, and other times he caught a ride with a longshoreman rowing across Long Island Sound to Connecticut and then traveled southward to the city. He enjoyed these trips, but the family was soon to face difficult times. In 1768, at the age of twenty-one, Adam died; six years later, at the age of thirty, Richard V died. And so, in 1774, Abraham found himself suddenly and unexpectedly in position to inherit the Woodhull family�s homestead.

It was a windfall he had neither hoped for when it was out of reach nor relished now that it was his. He had never considered himself cut from the same fabric as the rest of the prominent landowners, and had gone to some pains to distinguish himself from their upright and uptight behavior. Abraham Woodhull was proud of being the black sheep of his straitlaced family, and he assumed the burden of familial duty with reluctance; it smacked of Old World thinking. If he was to reject King George�s authority on the basis that the monarch had simply been born into his position, why could he not also reject his own family�s expectations for him to pick up the mantle of Woodhull respectability simply because he was the sole surviving son-of-a-son-of-a-son-of-a-son-of-a-son?

Woodhull had his sights set on Caleb Brewster as a fellow spy from the beginning. He had to admire the audacity of the brash longshoreman who was a bull of a man�physically huge and imposing�and was using his intimidating size and tremendous athletic skill to make himself a regular nuisance to the British. Ever the daredevil, he taunted them from his whaler laden with smuggled goods and then amazingly evaded capture. Just as Woodhull knew the landscape, Brewster knew the coves and the waterways, slipping out of reach of the British by ducking into one or another until the patrol gave up trying to catch him red-handed.

But that had always been Brewster�s way. Back in June 1775, some local men had circulated a document declaring their determination to fight British oppression, swearing that they would never �become slaves.� Despite his usual caution, Woodhull had signed it, as had one of Benjamin Tallmadge�s brothers. So, too, had Caleb Brewster. Remembering Brewster�s signature and observing the man�s high spirits and taste for adventure, Woodhull knew that Brewster would be an easy convert to the mission.

What Woodhull did not know was that Brewster had already embraced the thrill of espionage. The young man had been in correspondence with General Washington since July 1778�several weeks before Tallmadge had recruited Woodhull to manage the ring�reporting on the state of the British warships in New York Harbor, as well as troop movements and naval preparations around Long Island. His reports revealed little new information and were somewhat out-of-date by the time they reached Washington, but the gesture proved to the commander in chief that there were Patriots ready and willing to spy and that a well-organized ring of secret agents could yield real intelligence.

While taking care not to be overheard, Woodhull was probably rather direct in his proposal to Brewster. The man�s vigor and fearlessness in openly defying the British navy on the Sound left little doubt about which way his sentiments lay. Already hooked on the adrenaline rush of espionage, Brewster was an easy sell. He enthusiastically agreed to ferry messages to Connecticut and even offered to add his own observations to the reports headed to Tallmadge.

Woodhull supposed that his old friend Austin Roe, however, might prove somewhat more difficult to recruit. Roe was friends with Brewster, and while he was jovial and spirited as well, Roe was also comfortably situated, married, firmly established in his business, and took no joy in evading arrest in a rowboat for sport. But unlike Woodhull, who could find ready buyers for his produce in the city even if he alienated his Loyalist neighbors, or Brewster, who could find work as a longshoreman at any dock that needed the hands, Roe was a tavern keeper. His livelihood was entirely dependent upon the loyal patronage of local folks and the occasional traveler who passed his way and needed a room for the night. Should the spies� work be discovered, they could all expect something far worse than a loss of employment. But suspicions have a way of becoming whispers in small towns, and rumors about Roe�s activities could hurt his business even after the war.

Despite initial concerns, Roe was pleased by the mission and eager to offer his service in any way he could. Now a team of three, Woodhull, Brewster, and Roe devised a plan by which their intelligence would make its way across land and water to reach General Washington. Woodhull would operate from Amos Underhill�s boardinghouse in Manhattan, a location unlikely to arouse suspicion because of Woodhull�s family connection and because he already made fairly regular visits. The information he gathered would leave the city in one of two ways. Either Roe would make the trip into the city on the pretense of purchasing provisions for his business, or else Woodhull himself would travel back to Setauket, where he would leave the papers at Roe�s tavern or a predetermined location in a field near Roe�s house so the two men would not be seen together. This �dead-drop� method was less likely to raise suspicions but presented a much higher risk of a stranger�s stumbling upon the papers before they had been picked up, so the men rarely employed it. The two families were known to be old friends�Roe�s father had purchased the building he used for his home and business from the Woodhulls back in 1759�so nothing would seem out of place even if the two men were to be seen together carrying letters for the folks at home or visiting in the city. But Roe and Woodhull took care to ensure that the patterns of their meetings would not become too predictable and seem shady to nosy locals or eagle-eyed British soldiers.

Caleb Brewster, whose family lived just yards away from Roe, would wait for an opportunity to retrieve the papers from Roe. He would then dash across the water when the British navy had their backs turned. On the Connecticut side of the Sound, Tallmadge would be waiting for Brewster to dock and pass off the letters, which Tallmadge would then hand-deliver to the general.

The whole process took approximately two weeks from beginning to end and offered several advantages over the more traditional method of a solitary spy slipping in to gather intelligence and then slipping back out again. Local men were less likely to raise suspicions than an outsider who suddenly appeared in the town, skulked about for a few days, and then disappeared again. Using existing routines also allowed for a longer-term observance that could note changes in patterns and procedures of the troops. And, of course, if one man attracted suspicion, the seemingly convoluted method of passing off information from one member to another would make it much more difficult for the enemy to intercept sensitive documents. The intervening step of entrusting the papers to Roe was a brilliant one. It minimized the connection between Woodhull�s frequent trips to and extended stays in the city and Brewster�s regular dashes across the water and allowed the men to avoid apparent contact. But the proximity of Brewster�s home to Roe�s made their familiarity far more natural.

Even as the Culper Ring took shape, Tallmadge�s superior, Brigadier General Scott, still clung to the more conventional methods of dispatching spies. He had sent at least five men on separate scouting missions to Long Island, hoping to check their reports against one another for accuracy. He believed that even if one man was caught the others would not be compromised because each mission was conducted independently of the others. What Scott had failed to plan for was the capture of three of his five spies when their presence and suspicious behavior tipped off the British that all was not as it seemed.

Washington preferred this traditional approach at first, but it soon became clear that Scott�s method cost lives, and Washington�s conscience would not allow him to keep paying that high price. Battles demanded sacrifice, but Washington could not stand to see any more spies go the way of Nathan Hale�and all for nothing. Soon after his Long Island spies were caught, Scott took a furlough and returned home to Virginia to sort out some personal business. Washington appointed Tallmadge as his replacement. At the tender age of twenty-four, Benjamin Tallmadge became the chief of intelligence, the role that would define his career and ultimately help secure the nascent country�s future.

Espionage was, by no means, a gentleman�s game in the eighteenth century. In a world ruled by honor, a career of deception and duplicity carried little of the allure and intrigue that it would come to enjoy among later generations. Spies were everywhere, but the general rule was that one gathered intelligence for the sake of bragging rights later on, for the money it paid out now, for the glamorous life brought by proximity to those in power, or for sheer ideological fanaticism.

Mild-mannered, bookish Robert Townsend fit none of those molds. He was no braggart, had no sumptuous tastes or mercenary tendencies, and while he harbored certain tightly held beliefs, he was no zealot. He was a quiet boy from a prominent Long Island family with a history of independent thinking that he had inherited. A peaceable man, he did his best to stay out of the war�until an event forced him to take a stand.

Even as Robert Townsend was settling into his new role, something happened that highlighted the precarious nature of the world in which he now lived. On July 2, 1779, British raiders had attacked Major Tallmadge�s camp at dawn, killing ten men and capturing eight, plus a dozen horses. Those losses were devastating, but in the aftermath Tallmadge made a discovery that proved unsettling and was potentially threatening to the Patriots� intelligence operations. One of the horses the British had stolen was his own, which still bore its saddlebags and some of Tallmadge�s personal papers�including some money earmarked for Woodhull and a letter from Washington that specifically named George Higday, a resident of Manhattan �who I am told hath given signal proofs of his attachment to us, and at the same time stands well with the enemy.�

Eleven days later, Higday was arrested at his home and confessed to having met with General Washington to discuss the possibility of spying, but claimed that he never carried out any such activity because the payment had been in fake bills. There is no record of any punishment carried out against Higday; he was probably deemed harmless and sufficiently terrified not to be tempted into any covert actions in the future, so the matter was dropped. But Washington had now seen the dangers of using real names in correspondence and, again, felt the weight of the responsibility he had to guard the lives of those risking themselves for their shared cause.

Beyond Higday�s fate, there was another, even more immediate concern to the Culpers. On June 13, Washington had written to Tallmadge in regular ink and mentioned having a particular, special �liquid.� What was further, he referred to �C��r,� a common form of address for the day when a name was well known between two correspondents. The letter was intercepted and landed in the hands of the British prior to the July second raid, alerting them to the definite presence of an American spy in New York�one with whom Tallmadge was in close contact. The British had no way of knowing if C��r was a code name or a proper one, but they didn�t care. They were after bigger fish than just a spy; they wanted the spymaster himself, and the seized letter pointed straight to his camp.

Though Tallmadge had been fortunate enough to escape capture, he knew that damage had been done. If the ring were to survive, the spies would have to disguise information to protect it from prying eyes while keeping it understandable to those who depended upon the contents of the letters.

Alarmed by the two close calls, Tallmadge turned to the development of a code with a new sense of urgency. The ring had already begun to use a few numerical substitutions in their letters: for example, 10 stood for New York and 20 for Setauket, so that the recipient would know the source of the information contained in the reports. Two additional numbers, 30 and 40, were used to designate Jonas Hawkins and Austin Roe as post riders delivering the messages to their next destination. Tallmadge realized how essential it was that a more complete lexicon be developed and that every member or associate of the ring have a number rather than just a code name. In a style of cryptography developed originally by the French, Tallmadge selected a book and got to work. Making a list from 1 to 763, he pored over his copy of Entick�s Spelling Dictionary, the 1777 London edition, and assigned each pertinent word, location, or name a numeric code. He became 721, Woodhull as Culper Senior 722, Townsend as Culper Junior 723, Roe 724, and Brewster 725. General Washington was 711 and his British counterpart, General Clinton, was 712. Numbers were often represented by letters, so that the year �1779,� for example, might read as �ennq.� If a word needed to be made plural, or put in the past or future tense, a �flourish� would be written on top of it to designate the change.

The new system was not foolproof and required some adjustments on the part of the users, but Woodhull and Tallmadge were able to use it to correspond comfortably within a few weeks, though with a lingering sense of concern for what damage had been done by the intercepted message in June. In his same letter that mentioned the �[lady] of my acquaintance,� Woodhull opened:

Suspicions and tensions were beginning to rise even as the summer of 1779 reached its peak, and all the agents were feeling the stress. Washington sent �all the white Ink I now have (indeed all that there is any prospect of getting soon)� with a trusted colonel, along with the desperate instructions:

You will send these to C��r, Junr., as soon as possible, and I beg that no mention may ever be made of your having received such liquids from me or any one else. In all cases and at all times this procedure and circumspection is necessary, but it is indispensably so now as I am informed that Govr. Tryon [British governor of New York] has a preparation of the same acid or something similar to it, which may lead to a detection if it is ever known that a matter of this sort has passed from me.

Just four days later, Townsend prepared another letter for General Washington, closing with several lines that pointed to the increased danger he was also observing. �The times now are extreamly difficult,� he wrote. �Guard boats are kept out every night in the North and East Rivers to prevent any boats from passing, & I am informed that some persons have been searched on Long Island; therefore, whenever you think that my intelligence is of no service, beg you will notify me.�

Indeed, letters were now being searched with regularity as they left the city. Jonas Hawkins, the ring�s sometime courier, twice believed he was in danger of being found out and destroyed the missives he was carrying from Townsend, much to the older man�s annoyance.

On September 11, 1779, Woodhull acted as courier in place of Hawkins and wrote to explain what had happened to the letters from Culper Junior that had never made it to Washington as a result of Hawkins�s fear. �The bearer thought himself in danger. I believe it was merely imaginary,� Woodhull penned. �From timidity and the situation of affairs at the time, he did to choose to come to N.Yk; I therefore met him at a place quite out of danger on Long-Island. I then made an appointment�.�.�. at wch. time he came, I wrote it, and took it over the Ferry that he might run no hazard from the Inspector of Letters there.�

Townsend had never felt confident in Hawkins, having resented that his identity necessarily should be known by a boy he considered too immature for such serious work. For all of Townsend�s natural reserve, his reaction was almost certainly far from calm.

�He should have never been entrusted with such a task!� Townsend stormed to Woodhull when he learned of the destruction of his second letter.

�We needed another courier,� Woodhull tried to explain.

�But why am I risking my life gathering information day after day if my letters are to be destroyed before they reach the general?�

Woodhull shook his head. �The boy simply panicked.�

�But one who panics�or even looks nervous�before the inspectors is bound to bring extra scrutiny upon himself. And if he is searched and anything suspicious is found upon him, where will be the first place the British turn?� He paused, looking to Woodhull for an answer, but Woodhull just scraped at a bit of candle wax on the table. �They�ll look to any of his known associates, and to the last place he did business which, inevitably, will bring them to my shop,� Townsend finished, flatly.

�We are, all of us, on edge,� Woodhull said quietly.

�And we are, all of us, endangered by that boy�s want of good sense and composure.� Townsend banged his fist upon the table with such force it caused the candles to jump.

�I cannot always be coming here to retrieve your information myself. That will raise suspicions, too,� Woodhull insisted. �Besides, General Washington desires the information even more quickly than we have been supplying it. If you wait until I am able to make the trip, it will only delay the relay of news.�

�Then we get another man,� Townsend said, sighing and sinking into the straight-backed chair. �This time one who knows how to keep his wits about him.�

�But you were the one who insisted that your identity not be disclosed to anyone else. So what are we to do?�

Townsend dropped his head into his hands. The two friends discussed several scenarios, weighing the risks and benefits of each. Finally, they thought of Amos Underhill, Woodhull�s brother-in-law and the proprietor of the boardinghouse where Woodhull stayed on his frequent trips to Manhattan.

�He needs provisions as much as anyone else. Why could he not frequent my shop for goods and pick up the reports at the same time?� Townsend mused.

Woodhull considered this. �I�d still have to travel into the city to retrieve them, unless Amos could be convinced to come across the water sometimes.�

�But it would lessen your visits to my shop, and give us fewer opportunities to be spotted together. And he need not know the exact nature of our business together unless you deem it absolutely necessary.�

�It�s a gloomy thing to toast on,� Woodhull remarked. �But I agree that it�s a far better thing than to have young Hawkins destroy any more of your letters or, worse, be driven to madness and confess all. Give me a bit of time to present the matter to Amos and make proper arrangements. Until then, I will continue to serve as courier.�

One can hardly blame Hawkins for his trepidation; the threats were growing and the whole Culper Ring felt the squeeze. The pressure continued to mount as autumn approached. Besides fearing British searches, the couriers also faced dangers from increasingly active privateers. In his letter dated November 1, 1779, Tallmadge wrote to General Washington of the growing hazards faced by members of the ring, including the once-fearless Caleb Brewster: �The boat that crosses for dispatches from C�� has been chased quite across the Sound by those plunderers, perhaps for the sake of being the more secret in their Villany, while our crew has suspected them to be the Enemy. Indeed if some stop cannot be put to such nefarious practices C�� will not risque, nor 725 [Brewster] go over for dispatches.�

By the end of November, Amos Underhill�s name began to appear regularly in Townsend�s ledger. Hawkins, meanwhile, seems also to have questioned his involvement and quietly removed himself from the ring. Underhill�s appearance could not have been better timed, as Woodhull�s nerves were again getting the best of him. Woodhull had been questioned by a party of British troops while en route to meet up with Townsend at a safe house on Long Island, but apparently he kept his wits about him, because he was released without having to succumb to a more thorough search; Townsend, however, did not show. Woodhull waited at the rendezvous point the next day as well, but there was no sign of Culper Junior. The excuse for his absence does not appear in any of Townsend�s letters, but as he was quite condemning in his correspondence of others who failed to make appointments, it was undoubtedly a serious matter beyond simply a lack of courage. The slip brought Woodhull nearly to a breaking point, prompting him to tell Tallmadge afterward that he had endured �a full year�s anxiety, which no one can scarcely have an idea of, but those that experience. Not long since, there was not even the breadth of your finger betwixt me and death.�

Woodhull�s complaint was not unwarranted. The residents of Long Island were bracing for an even greater number of troops to be quartered there during the coming winter than they had endured the winter before; they also continued to absorb Loyalist refugees from all over the eastern seaboard. �The inhabitants of this Island at present live a miserable life, which you may readily judge when having the refuse of three kingdoms and thirteen States amongst them. Plundering and rapine increaseth at no small rate,� Woodhull wrote in the same letter to Tallmadge. �I am tired of this business, it gives me a deal of trouble, especially when disappointments happen. Could not consent to be any longer an assistant if I was not almost an Enthusiast for our success.�

But there was a covert storm brewing in New York�one that Townsend was in the process of uncovering and confirming�that threatened the Americans not through bloodshed or siege, but through their pocketbooks. And if it was on account of uncovering this business that Townsend was unable to meet up with Woodhull, he might very well be excused by reason of the magnitude of the plot he thwarted.

Now Washington had tasted victory; his agents had outsmarted the enemy in their own territory. It could be done. By revealing the counterfeiting plot, the Culper Ring had proved that New York was not some insurmountable fortress; they had penetrated its vault of secrets successfully and unmasked an entire plot before it could be played out to its catastrophic end. Best of all, the enemy had no way of knowing at what stage the plan may have been leaked or tracing back any breaches of secrecy. Washington�s informants, therefore, were relatively safe from detection and could continue their activities without too much concern for their welfare.

Even so, there was much more afoot�of that Washington was certain. Now that one plan had been foiled another would soon be hatched, probably with more speed this time to minimize the risk of leaks. Some delicacy must be sacrificed for the sake of urgency, but could he make his most trusted, most valued, and most secretive ring understand that? He pored over the maps as he would before a battle; perhaps there was a way to convey messages across the Hudson River or via Staten Island? He wrote as much to Tallmadge, urging him to talk to Culper Senior about such an option, hoping to impress upon the ring the importance of timely reports.

The Culpers, meanwhile, were enjoying something of a reprieve from the oppressive worries that had plagued them of late. Colonel Simcoe had left his reluctant hosts, the Townsends, and led the Queen�s Rangers back to the mainland in an effort to capture George Washington. They had failed, and Simcoe was now being held prisoner by the Americans. Woodhull, no doubt voicing the sentiments of numerous people, concluded his letter to Tallmadge on December 12, 1779: �Were I now in the State of New Jersey without fear of Law or Gospel, [I] would certainly kill Col. Simcoe, for his usage to me.� In that same message, he included a blank sheet containing a stain letter from Townsend with whom he wrote he planned to celebrate Christmas.

Holiday leisure was a luxury the commander in chief could ill afford as the fate of the entire Revolution rested heavily upon his shoulders. Even as Woodhull wrote that his �fears are much abated,� Washington felt a growing sense of urgency to see the cracks in New York�s armor exploited even more aggressively. Matters in the southern colonies showed signs of deteriorating come spring, which meant that his attention and resources would be even more divided and strained. If the British were plotting any offensive maneuvers from the city, he wanted to be prepared.

Washington must have communicated his urgency to the ring, because Amos Underhill visited Townsend�s shop with increased frequency starting in mid-January 1780, appearing in his ledger four times in just over three weeks. But the smuggled messages were not meeting the pressing demands Washington was facing. Events were accelerating rapidly, and the laborious means of conveying the letters out of occupied New York and Long Island, into Connecticut, and overland to Washington�s camp were too slow. Instead of providing new information, the Culper Ring�s intelligence was now providing verification of facts the general had already learned. �His accounts are intelligent, clear, and satisfactory, consequently would be valuable, but owing to the circuitous route through which they are transmitted I can derive no immediate or important advantage from them,� Washington wrote Tallmadge on February 5. �And (as I rely upon his intelligence) the only satisfaction I derive from it, is, that other accts. are either confirmed or corrected by his, after they have been some time received.�

He was not unsympathetic to the tremendous challenges his ring faced�most specifically, the risks Culper Junior, who lived and worked in the heart of the British operations, endured every day. �I am sensible of the delicacy of his situation, and the necessity of caution,� Washington added to his letter, as if realizing the harsh tone of his criticism in the preceding lines directed to his favorite spy. He went on to suggest that he may be able to provide Culper Junior with more direct possibilities for moving the letters out of New York, though he acknowledged the risks involved in expanding the ring beyond its current members: �I have hitherto forborn and am yet unwilling to mention, persons to him as the vehicles of conveyance lest they should not prove so trustworthy and prudent as we could wish.�

A few weeks later, Woodhull found himself writing back to Washington, informing the general of detailed ship movements, as well as warning him of even more potential risk from greatly increased scrutiny and enemy presence in Setauket: �Two regts. is to be stationed in this Town. If it should take place it will I fear entirely ruin our correspondence. To prevent which I shall give you early intelligence of their motions from time to time, that you may be prepared to give them a fatal blow at the beginning, or we shall be totally ruined.�

The reprieve Woodhull�s emotions had enjoyed in December had proved all too brief. It was March now, which meant increased activity could be anticipated with the spring thaw. But the winter of 1779�80, known as �the Hard Winter,� proved to be one of the coldest recorded seasons of the eighteenth century in North America, and refused to let up. The weather took a turn for the worse, with tumultuous spring storms thwarting several efforts to convey letters to Washington explaining that the Culpers had taken seriously his concerns regarding the speed of their reports. Under increased pressure to perform, Woodhull once again let his nerves get the best of him as he attempted to count and recount the blank sheets of paper that had come to him as part of his last batch of goods from Townsend. Somehow, the number never seemed to come up right and the same sheet was never landed upon twice. Worried about sending a worthless paper rather than the one that contained the message written in the stain, Woodhull finally threw up his hands and dashed off a note: �Sir. Inclosed you have a blank�Something fearful not sending the right and have inclosed three.�

General Washington could not hold a grudge for long. After cooling off for several weeks and realizing that no real harm had been done by the misadventures of James Townsend, he began to reconsider his decision. Slow but credible intelligence was better than fast but muddled�or no intelligence at all. Washington had grown accustomed to his reliable and detailed reports from the Culper Ring; those messages provided him with a sense that something was happening to advance the Patriot cause in New York, even if he was powerless to lead the charge to recapture the city.

Meanwhile, the same rumor that Clinton had heard grew to a buzz. A fleet of French ships was crossing the Atlantic at that very moment, coming to give the Americans a much-needed boost of men, might, and morale. If the British intercepted them it would be devastating.

Washington did not know where the French would land. He did not know whether the British knew, and, if they did know, how General Clinton was planning to ambush the fleet. Even great men make mistakes, and Washington knew he had committed a grave one in ending the spy ring. Never before, he realized, had he needed eyes and ears in New York so urgently. It had taken a long time to win over France, and the Americans could not afford to squander their new ally�s good favor.

Even as the Americans were congratulating themselves on the success of their counterintelligence, a traitor was building his own network within their midst. In the early summer of 1780, just as the Culper Ring was entering its hiatus and Clinton and Andr� were settling back into New York after their foray to South Carolina, Major General Benedict Arnold was working to get his hands on a new command. Though he had been living the high life in Philadelphia, some recent unpleasantness had wounded his ego, and he had found himself in an all-too-familiar position: humiliated, angry, and desperate to prove his worth. He was about to show the world just how important he really was. If the Americans couldn�t see his value, the British would.

Arnold had been a man with something to prove right from the start. Despite his current rank of major general in the Continental Army, he was profoundly insecure and carried a chip on his shoulder from a lifetime of feeling perpetually slighted by fate. Given the paternal name of �Benedict� after an older brother bearing the same name died in childhood, Arnold started out life living in the shadow of someone else, and no matter his later successes, he always seemed plagued by insecurities and a sense of somehow always falling short.

Unable to attend Yale due to his father�s financial woes brought on by alcoholism and poor health, Arnold was forced to learn a trade instead. He apprenticed with two of his maternal uncles in their apothecary and mercantile shop but longed for something greater. In 1755, at the age of fourteen, he begged to be allowed to join the colonial militia that was in service of the king of England in the French and Indian War. His mother forbade him to do so, but two years later he enlisted anyway, only to leave the militia the following year, allegedly deserting.

However he came to be separated from his first term of military service, he proved to have a strong business sense and by his early twenties was running a successful pharmacy and bookshop in New Haven, Connecticut. Eventually he was able to purchase partial ownership in a small fleet of merchant ships and occasionally sailed on trading ventures to the Caribbean. With the increase of British taxation, starting with the Sugar Act in 1764 and the Stamp Act the next year, Arnold felt the pinch but followed the example of many American merchants who simply ignored the laws they viewed as unwarranted and unjust from a government that taxed its colonial citizens without granting them representation in Parliament.

In 1767, he married Margaret Mansfield, a hardworking and prudent woman who proved a valuable partner to him, thanks in large part to her family�s solid standing in New Haven, where her father served as sheriff. Arnold began to fall on financial hard times and accumulated some substantial debts, but he continued in his trading business even as his outrage over the political climate in the colonies increased. On March 5, 1770, British soldiers fired into a crowd of protesters in Boston, killing five civilians and wounding six. The Boston Massacre infuriated Arnold. He had been in the West Indies at the time, so the news did not reach him until more than a month after the fact, but it stirred in him a profound sense of action and responsibility. �Good God,� he wrote on June 9. �Are the Americans all asleep & tamely giving up their glorious liberties or, are they all turned philosophers, that they don�t take immediate vengeance on such miscreants; I am afraid of the latter.�

In March 1775, Arnold joined the Connecticut militia as a captain and just two months later received a colonel�s commission in the Massachusetts Committee of Safety after he offered plans for attacking the British outpost at Fort Ticonderoga in northern New York. The mission was a success and Arnold garnered accolades for his performance, but he resigned his commission after a disagreement with another militia leader. He then set out to return home to serve in Connecticut. Bad news seemed to have a way of reaching Arnold whenever he was traveling, and he was on the road when he learned his wife had died.

Over the next few years, Arnold was involved in a number of key American victories and distinguished himself as an insightful strategist and able officer. But his talents were not nearly so celebrated as Arnold believed was his due. His advice was often heeded, though he was not sought out as a leader; he was passed over for command and promotion several times, which deeply wounded his ego. He became a polarizing figure, either loved or loathed by his comrades in arms. Those who argued in his favor pointed to his keen understanding of strategy and shrewd assessments of the enemy�s vulnerabilities. Those who argued against him pointed to his quick temper, his growing pessimism toward the success of the American war effort, and his apparent motivation by personal glory and gain. Colonel John Brown, one of Arnold�s rivals, prophetically wrote of him in 1777: �Money is this man�s God, and to get enough of it he would sacrifice his country.�

After distinguishing himself in the Battles of Saratoga in the fall of 1777, Arnold believed he had finally shamed his critics and detractors who were standing in the way of the meteoric rise he so desperately desired. His valor in combat was undeniable�even though he had acted in direct defiance of an order from his superior officer, with whom he had a personal dispute. He had been severely wounded in his left leg but refused to allow an amputation; instead, he had it set to heal, but the job was poorly done. As a result, Arnold walked with a limp for the rest of his life.

In June 1778, as the Americans were reestablishing their presence in Philadelphia�and roughly two months before Woodhull began spying in New York as Culper Senior�Washington appointed Arnold the military commander of Philadelphia. Arnold quickly realized that this new position would allow him to engage in a variety of business deals to restore his finances, which were still plagued by his numerous debts back home in New Haven. He was not particularly popular among many citizens of Philadelphia, however, and complaints were soon raised that not all of his ventures were legitimate. One vocal critic was Allen McLane, a highly respected and distinguished soldier from Delaware, who had been among the first Americans to enter Philadelphia when the British left; McLane voiced his concerns to General Washington but was reprimanded for challenging such a high-ranking officer. When Arnold learned about the complaints, he was angry that so many citizens and fellow soldiers questioned his integrity, particularly because his position was one of public service to a war-torn city. Was he not an officer of the Continental Army who was fighting for the liberty and freedom of all Americans?

This upturn in his fortunes pleased Arnold, and he lived well in Philadelphia, even under the shadow of accusations that his gains were ill gotten. Like his British predecessors, he enjoyed rich furnishings and luxurious dinners and entertainments. He even mingled with Philadelphia�s society belles, one of whom, Peggy Shippen, especially caught his attention.

Benedict Arnold�s treason was well under way when the French fleet arrived in Newport during the summer of 1780. Observing that Washington was actively working on several covert plans to outmaneuver the British, Arnold tried just as actively to undo them in secret. Fortunately for Washington, the deep secrecy surrounding the Culpers kept the ring out of Arnold�s reach, but the success of the spies� tip and Washington�s ruse had alerted Benedict Arnold. He knew he would need to infiltrate or stop the ring were his betrayal to be successful. Little did he know that members of the very ring he was attempting to ensnare were removed from him by just a few degrees of separation.

At the end of July, with the French troops safely disembarked in Rhode Island, Washington prepared to ride out to meet them and proposed that Arnold lead a raid against some of Clinton�s troops stationed around New York at the same time. Arnold pleaded to be excused from such exertion, using the same reasoning he had back in March to remove himself from other action: An injury had left him with a stiff ankle, and his doctors had recommended that he not take command of an army until it healed. Conceding to Arnold�s requests and complaints, Washington kept him off the battlefield and diverted him instead to the less physically demanding post as commander of West Point, exactly as Arnold had hoped. On August 3, 1780, Benedict Arnold found himself the most powerful man on the Hudson.

He wasted no time in capitalizing on his new position. Almost immediately he began repairing the fort and stocking it with as many provisions as possible. If he was going to turn West Point over to the British, he might as well win points with his new commanders by outfitting it on the American dime first; he even consulted a French engineer fighting alongside the Americans, Major Chevalier de Villefranche. �Major Villefranche has surveyed the works at West Point, and informs me that there is a vast deal to do to complete them,� Arnold wrote Washington on August 8. �That large quantities of materials, such as timber, plank, boards, stone, &c., will be wanted. Part of the materials are at different places near this post; but I do not find that there are any teams or forage in the department, and, at present there is no prospect of any being furnished.�

Even more urgently, Arnold began to inquire about the names and addresses of Patriot spies he claimed might be of importance to him in defending the fort against any planned attacks by the British. Of particular interest to Arnold was the ring operating in New York, upon whom Washington had relied so heavily in the recent incident with the French fleet as well as in previous matters of significant intelligence, such as troop movements on Long Island and the foiled counterfeiting plan. The commander in chief declined the request out of both honor and necessity; he did not know the identity of most of his spies by design and he had sworn to uphold the secrecy of those he did know. Lafayette responded to Arnold�s request in a similar manner.

Disappointed that he was not able to ensnare the Culpers, which would have delighted General Clinton no end, Arnold nevertheless pursued whatever prey he could. On August 5, Arnold wrote a letter to Major General Robert Howe of the Continental Army, begging for this same information about a few operatives in Howe�s employ in such an eloquent and reasonable manner that his motives seemed quite aboveboard. �As the safety of this Post and garrison in a great measure depends on having good intelligence of the movements and designs of the enemy,� he penned, �and as you have been fortunate in the agents you have employed for that purpose, I must request, with their permission, to be informed who they are, as I wish to employ them, for the same purpose. I will engage upon them to make no discovery of them to any person breathing.�

Howe replied nine days later in a manner that shows he was clearly distressed by his spies� response at the time, though it must have seemed a tremendous blessing only a few weeks later when Arnold�s true nature was revealed:

The two most intelligent and confidential I got to undertake with difficulty, and they did it with the greatest reluctance and not without my pledging in the most solemn manner my honor not to inform any person upon earth of their names, or of their acting in the capacity of emisarys, they are persons of character and property, who cannot without utter ruin get out of the enemy�s power, and yet devoted to America, have agreed to serve in a way they do not like, but which is the only way they can at present serve her in. I have written to them and urged them to let me give their address to you, but�.�.�. they in the most positive terms refused; and it is not without great persuasion and difficulty that they are prevailed upon to continue their acting even for me; this makes me fear they will not consent to it tho I sincerely wish they may. I cannot indeed blame this caution, as their life and the ruin of their families must be the certain consequence should any accident happen to them.

Howe did manage to persuade one operative in his employ to correspond with Arnold, though this was under an assumed name. �He will mark the letters Private, and you must injoin your family not to open any letters so marked,� Howe warned in the closing of his message.

Arnold�s response was gracious, if disappointed. He had clearly anticipated obtaining specific details about the various covert operatives at work in and around New York that he could pass on to Andr� via Peggy, but had learned almost nothing. He pledged his honor to Howe that he would not expose the one man who had agreed to send information to Arnold, nor reveal his name should he accidentally discover it. In a culture where a man�s honor was considered quite sacred, these sentiments seem especially crass given Arnold�s intention, but, to his credit, he was not entirely disingenuous. �I will take proper precautions that no gentlemen of my family open any letters addressed to me as Private,� he added. Peggy, after all, was not a gentleman.

On the afternoon of Sunday, September 10, 1780, Benedict Arnold stepped onto a barge under the auspices of meeting with his long-awaited merchant friend from New York, John Anderson. If the general seemed nervous or anxious, the bargemen took no notice. They, too, were probably on alert for British gunboats patrolling the waters of the lower Hudson River and were not especially delighted with the thought of traveling southward toward enemy territory. They followed the river several miles, then let Arnold off on the shore to stay the night at the home of a friend who lived near the river. The next morning, the crew sailed the approximately twenty miles remaining, to Dobbs Ferry, where the meeting was to take place.

As the barge approached, a barrage of British gunfire opened up on the little vessel, which quickly retreated upriver a safe distance. Arnold, who had not anticipated this attack, ordered the crew to land the barge on the west bank of the river, where he could safely await Anderson�s arrival at a small outpost of American troops. The merchant never appeared, and Arnold, forced to declare the meeting a failure, returned to West Point. Andr�, it turns out, had been in the vicinity, but the vigilant gunboats had made crossing the river quite perilous in risking both his life and recognition by some of his own soldiers. He returned to New York to arrange a second attempt at meeting with his coconspirator.

Colonel Simcoe, the cold-blooded leader of the Queen�s Rangers who had occupied the Townsend Homestead in Oyster Bay, had some time past been ransomed from his prison in New Jersey and was once again commanding his men on raids. Andr� had promised him the privilege of being present for the surrender of the fort, but Simcoe now received word that the rangers were being ordered to ride south toward Chesapeake Bay and wrote to Andr� greatly worried that this sudden change would cause him to miss out on the fun. �Rely upon it your alarms are vain,� Andr� wrote the day after his missed rendezvous with Arnold. He added, tantalizingly, �I should have been happy to have seen you and have hinted that apparent arrangements are not always real ones, but I beg you to seek no explanation.�

On September 15, Arnold penned a letter to �John Anderson� recounting the failed meeting and attempting to set up another opportunity �on Wednesday the 20th instant� at the same location. (�Instant� was a form of eighteenth-century shorthand meaning �of the current month.�) He may have regarded their missing each other as a bad omen, and was certainly feeling agitated and exposed. �The foregoing letter was written to caution you not to mention your business to Colonel Sheldon, or any other person,� he warned, clearly concerned that Arnold might play his part as a Patriot merchant too convincingly by chatting with the leader of the Light Dragoons as he passed through their patrol area. �I have no confidant. I have made one too many already.� The letter, which he signed �Gustavus� as he had several of this series of messages, was directed toward New York, and Arnold returned his attention to making his preparations.

He had been quite eager to learn the itinerary of General Washington, a fact that Alexander Hamilton later noted may have been an attempt to secure the commander in chief�s capture along with the fort. In fact, Arnold�s letters indicate that he was anticipating Washington�s arrival at West Point in a matter of days with the intent of the general�s staying Saturday night at the fort. The main focus of the plan, however, was to secure the handover; Arnold, after all, was acting more from a sense of monetary gain than from any deep-seated political zeal regarding who would ultimately win the conflict.

Major Benjamin Tallmadge respected the chain of command and he respected his senior officers, but in this instance he knew that his commanding officer had made a perilous mistake. Colonel Jameson had sensed that something was amiss, because he had rushed the papers found on the prisoner to Washington for examination, but fear of displeasing Arnold had clouded his better judgment, prompting him to return the prisoner to Arnold as he requested. Chagrined, Jameson was willing to listen to his subordinate�s suggestions.

Tallmadge was a spymaster and much more savvy about the backhanded operations of intelligence gathering than Jameson. Hearing a full account of the story, he recognized the seemingly disparate pieces and concluded that a major betrayal was at hand. His first thought was to suggest a daring mission designed to entrap all the involved parties. He proposed the scheme to Jameson, who found the plan much too bold. Tallmadge later wrote to a friend and historian: �[I] did not fail to state the glaring inconsistency of their conduct to Lt. Col. Jameson in a private and most friendly manner. He appeared greatly agitated, more especially when I suggested to him a plan which I wished to pursue, offering to take the entire responsibility on myself, and which, as he deemed it too perilous to permit, I will not further disclose.�

With his first suggestion rejected, Tallmadge immediately pursued the next best way of intercepting the prisoner and returning him to their custody. Jameson remained hesitant, afraid of upsetting General Arnold, but Tallmadge finally managed to persuade him to rescind his order and bring Andr� back to North Castle while they awaited word from Washington. Oddly enough, Jameson still insisted on informing Arnold of the turn of events. �Strange as it may seem,� Tallmadge wrote, �Lt. Col. J. would persist in his purpose of sending his letter to Gen. Arnold�The letter did go on, and was the first information that Arch Traitor received that his plot was blown up. The Officer returned [to Jameson�s camp] with his prisoner early the next morning.�

Jameson�s decision to alert Arnold to the matter, while shocking in retrospect, was quite understandable, given Arnold�s reputation. For one thing, Arnold was widely trusted by many officers of the Continental Army; even those who held him in contempt would generally not have anticipated that his imprudence could go so far as to commit treason. Tallmadge noted later that Jameson, in writing to Arnold about the matter, �expressed great confidence in him as I believe was the case thro� the army. Until the papers were found on Anderson, I had no suspicion of his lack of patriotism or political integrity.� For another, Arnold was widely feared, and Jameson was willing to take extreme steps to protect himself from the man�s wrath for not following his directives. Had Tallmadge not been as acutely attuned to subtle clues and not been actively trying to piece together the Culper Ring�s reports, he, too, might have fallen under Arnold�s spell and failed to realize who John Anderson was.

Even now, Tallmadge kept the spies in mind and realized that more than just the fate of Fort West Point was at stake. The surrender of the fort had to be stopped at all costs, but in a somewhat delicate way. Andr� would not have broadcast his travel plans beyond a select circle, and the collapse of his plan could endanger the spies who had helped unravel the plot. If word reached the British that there was a mole in Andr�s inner circle, Agent 355 and any of her associates�like Townsend�could be quickly unmasked. The entire ring would collapse, and the gallows would become a little more crowded. Tallmadge would have to act swiftly but carefully.

Although Arnold was exposed, the plot to surrender West Point was shattered, and Andr� was dead, the danger to the Culper Ring was still very much alive. �I am happy to think that Arnold does not know my name. However, no person has been taken up on his information,� Townsend noted in a letter to Tallmadge. Clearly, Townsend was anticipating what all of the covert operatives must have been dreading�that Arnold would disclose the identities of any spies known to him in order to keep himself in the good graces of the British.

This fear was not paranoia; something similar was certainly happening on the American side, where many of Arnold�s comrades and confidants, including the shady Joshua Hett Smith, were being arrested and interrogated to learn who may have been in cahoots with the general and who had merely been manipulated unwittingly. The links of the Culper chain and every independent spy in New York�perhaps in the whole of the colonies�were all on edge, well aware that they would be the target of Arnold�s wrath if he had any indication of their identities, and that he was likely to seek revenge on anyone he�or the British�suspected might have had knowledge of any part of the failed plot.

Tallmadge was keenly aware of their concern, and wrote to Washington on October 11:

The conduct of Arnold, since his arrival at N.Y. has been such, that though he knows not a single link in the chain of my correspondence, still those who have assisted us in this way, are at present too apprehensive of Danger to give their immediate usual intelligence. I hope as the tumult subsides matters will go on in their old channels.

Culper, Junr. has requested an interview with me on Long Island on the 13th inst[ant], but in the present situation of affairs I believe it would be rather imprudent.

Washington understood the perilous state of all the members of the Culper Ring, and judged Tallmadge�s avoidance of a covert visit to Long Island at this particular point in time as quite wise. �I think you were right in declining an interview at this time, as the enemy would act with more than common rigor just now should an officer be taken under circumstances the least suspicious,� he wrote back, though he added, �I should be exceedingly glad to hear from C. Junior.�

On October 15, Washington wrote to the president of the Continental Congress (at that time, Samuel Huntington of Connecticut), informing him of several matters and noting with regard to Culper Junior: �Unluckily, the person in whom I have the greatest confidence is afraid to take any measures for communicating with me just at this time, as he is apprehensive that Arnold may possibly have some knowledge of the connection, and may have him watched. But as he is assured, that Arnold has not the most distant hint of him, I expect soon to hear from him as usual.�

Townsend�s return to spying was not as swift as Washington seems to have hoped, however. Woodhull sent a letter dated October 26, in which he explained: �I have this day returned from New York, and am sorry to informe you that the present commotions and watchfullness of the Enemy at New York hath resolved C. Jur. for the present time to quit writing and retire into the country for a time.�Most certainly the enemy are very severe, and the spirits of our friends very low.� In an interesting show of steeling his nerves, despite his earlier anxieties�perhaps because he recognized how much safer he was in comparison to the spies who had worked closely with the British officers in New York�Woodhull volunteered his services while Townsend was on hiatus. A few weeks later, he wrote again, �Depend my endeavours shall continue, as I hope never to lose sight of our cause, truly sensible our all is at stake.�

With the death of Andr�, the British found themselves without a spymaster at a time when such an officer was particularly important. Things were heating up in the south again, particularly in Virginia, where Arnold (with poor Champe in tow) had sailed with fifteen hundred troops in December 1780. Clinton found his attentions drawn to the Chesapeake even as the raid at Fort St. George had proved that New York could not be left unattended. A man was named to fill Andr�s vacancy and manage intelligence for the commander of the British troops on American soil.

Major Oliver DeLancey was in his early thirties�a New York City native whose family was among the earliest Jewish settlers in the American colonies. He had been educated in England but returned home soon after the war began in order to organize a Loyalist regiment in New York. He may not have had the same level of star appeal that Andr� enjoyed, but he was brilliant, able, and now operating in his native territory, which gave him a distinct advantage in understanding the people, customs, and terrain. He immediately set about to reorganize the British intelligence system, unifying codes and bringing a number of disparate and independent elements together so that information could more easily be shared, analyzed, and acted upon.

The Culper Ring, in the meantime, stayed busy (if not active in spying) as the calendar turned from 1780 to 1781. Late in the winter, Caleb Brewster captured a British boat and eight prisoners, including two officers. Townsend resumed his business and reopened his shop in the city in March. Woodhull tried to persuade him to start gathering intelligence again, but Townsend believed that the British had dispatched a spy of their own in New York who was actively trying to root out the sources and paths of the Culpers� information and insisted on lying low. The matter was dropped until the end of April, when Tallmadge could finally report the pending resurrection of the ring�s activities, with a few adjustments made to their former routine. �The plan which he [Woodhull] has consented to adopt, on certain conditions, is for him to remain for the most part on Long Island and C. Junr. whom he thinks might be engaged again, to reside constantly at New York,� he wrote to Washington on the twenty-fifth. �That some confidential person must of course be employed to carry dispatches as it would cause suspicions which might lead to detection if either of the Culpers should be frequently passing from New York to Setauket, &c. they being men of some considerable note.�

Washington preferred a more timely delivery of intelligence, but he agreed to this arrangement. The Culpers� reports were essential to the continued success of the Americans, even if they did take a few days longer to arrive. The general had learned from his earlier mistake; vital information received a few days late was infinitely preferable to no information at all. He quickly replied to Tallmadge:

The great object of information you are very well acquainted with�such as, Arrivals, Embarkations, Preparations for Movements, alterations of Positions, situation of Posts, Fortifications, Garrisons, strength or weakness of each, distributions and strength of Corps, and in general every thing which can be interesting and important for us to know. Besides these, upon a smaller scale, which are necessary to be reported: and that whatever intelligence is communicated ought to be not in general terms, but in detail, and with the greatest precision.

At present I am anxious to know (for the reports have been very numerous vague and uncertain) whether another embarkation is preparing, and if so to what amount, and where destined. What the present force of the Enemy is; particularly on Long Island, in New York and at King�s Bridge. What Corps are at the latter place, how strong, and where posted exactly�and indeed what the situation, prospect, and designs of the enemy are, so far as they can be penetrated into.

Washington�s instructions are vast in their scope and display the extreme confidence he had in his most valuable ring to obtain precisely the breadth and depth of intelligence he required. He took pains in the same letter to note that he was �engaging in behalf of the United States a liberal reward for the services of the C��s, (of whose fidelity and ability I entertain a high opinion) it is certainly but reasonable, from patriotism and every other principle, that their exertions should be proportionately great, to subserve essentially the interest of the Public.�

Despite Washington�s praise, Townsend adamantly refused to put pen to paper. He had seen how Andr� had been done in by the discovery of papers and plans�hard and damning evidence he could not deny or talk his way out of. He would be happy to convey orally whatever information he had observed, Townsend explained to Woodhull when they met in the city in early May, but the risk of trying to smuggle written documents out of Manhattan was far too great. Woodhull could not deny the truth of those concerns, especially now that Oliver DeLancey was asserting his authority with new ideas for uncovering plots in their midst.

In his May 19 letter to Tallmadge, Woodhull noted that, on the way back to Long Island from visiting Townsend, �the enemy must have got some hint of me for when passing at Brooklyn Ferry was strictly examined and told some vilian supported a correspondence from this place.� The letter also included intelligence Austin Roe had obtained verbally from Townsend on his last visit to the city, but they all knew their visits could not be so frequent as to raise suspicions. Woodhull and Townsend worked exhaustively to recruit a new member for the ring, one who was not already under the watchful eyes of British operatives and could operate freely in Manhattan and smuggle out detailed written reports. �When at New York myself, together with Culper Junior [we] almost racked our invention to point out a proper person and made several attempts but failed�no person will write,� Woodhull lamented.

The year 1783 dawned full of promise. On February 3, the government of Great Britain formally acknowledged the independence of what were once its American colonies as the United States of America. The following day it agreed to halt all military involvement. In April, a preliminary peace treaty was ratified, and in July tracts of land in Canada were opened to Loyalists seeking a new life and a region was designated for former slaves who had fought for Britain. Crowded ships bound for Nova Scotia and New Brunswick sailed northward from New York Harbor. But still, the British army remained firmly and fixedly in Manhattan.

North of the city, near his encampment in Newburgh, Washington was struggling to subdue a rising insurrection against the back wages owed and promises of land that had been offered to Patriot soldiers but which Congress had failed so far to deliver. Combat may have reached an end, but the enemy still would not leave and the daunting task of rebuilding the country while paying down the debts of war loomed as challenges still to be faced.

Woodhull, meanwhile, continued to send the occasional report from Long Island, though there was nothing of great urgency or importance anymore. The Culpers had done their duty, and done it well. A note dated July 5, 1783, was accompanied by a final balance record that Woodhull submitted to Tallmadge, at the major�s request: �I only kept the most simple account that I possibly could, for fear it should betray me, but I trust it is a just one�and I do assure you I have been as frugal as possibly could. I desire you would explain to the Genl. the circumstances that attended this lengthy correspondence that he may be satisfied that we have not been extravagant.� Woodhull then concluded the letter in a way that clearly reflected the present optimistic mood on Long Island: �Wishing you health and happiness, I am your very humble servant, Sam^l. Culper.�

After five years, four major plots thwarted, countless misgivings and close calls, and untold sleepless nights, the Culper correspondence came to an end. The ring had operated effectively from the very heart of the enemy�s headquarters and had never been successfully infiltrated, uncovered, or unmasked, despite numerous efforts in that vein. The loss of Agent 355 was a tragedy, but it was also remarkable that the casualties were not much higher given how close the Culpers were to the enemy in Manhattan and the daring movements and maneuvers of the agents on Long Island. While the spies had not been able to deliver Manhattan to Washington before the war�s end, they had been his eyes and ears there, enabling him to beat the British even without holding the city. The Culper Ring was a success.

All that remained now between Washington and his spies was the settling of some small monetary debts; the larger debts�the intangible kind that helped to protect a fledgling nation�could never be fully repaid, nor did the remaining members of the Culper Ring seek out such payment. A return to an open, honest, and simple life in an independent nation founded on their native soil would be reward enough. And so they hoped, and prayed, and waited for the British to depart from New York at long last, even as the aftermath of war swirled around them.

With the end of the war and the start of the American republic, the Culpers could return to their lives as ordinary citizens. While a few were not shy about their role in the war effort and enjoyed a bit of notoriety for their daring adventures, most did what all good spies do: They carried on in obscurity as ordinary and unassuming people whose neighbors never knew they had led double lives. Their stories were packed away like pressed flowers in the pages of a book�quietly waiting, undetected for years�to reward some curious reader decades later with the intricacy and beauty of their design. There were whispers, rumors, and legends, of course�but no one pursued them, happy to leave well enough alone when the desired outcome of liberty had been reached, though at a high and terrible cost.

Caleb Brewster, after his years of excitement rowing back and forth across Long Island Sound in his whaleboat and engaging in hard-fought skirmishes, found that the second part of his life was much quieter than the first, though he was never far from the sea. He married Anne Lewis of Fairfield, Connecticut, in 1784, and moved to a farm at Black Rock, southwest of Bridgeport, where the couple had several children. Brewster passed away at his farm on February 13, 1827, and for all of his prodigious feats of bravery and skill during the war, his headstone notes his eventual rank of captain and then sums up his service simply: �He was a brave and active officer of the Revolution.�

James Rivington had a less tranquil retirement. According to George Washington Parke Custis, during the private meeting between Washington and Rivington in the bookshop, the officers in the front room could distinctly hear a bag of gold coins being handed to the bookseller for his spying services during the war. Custis, however, was not actually present for the events and had a habit of occasionally embellishing stories in accordance with his own imagination. Whether gold really changed hands during this meeting or not remains unclear. But what is certain is that Rivington and his shop received special protection in the days and weeks following the British evacuation; there would be no burning and looting as had occurred at the hands of the Sons of Liberty in 1775. Later correspondence of Washington�s confidants defended Rivington against libel. He remained in New York, though his newspaper business suffered because of his reputation as a staunch enemy of the new republic. He was eventually forced to close his shop, but with eight children to support back in England, several bad investments, and a personal taste for the high life, his financial situation deteriorated until he was forced to serve time in debtors� prison. He died in New York, where he had spent thirty-six of his seventy-eight years of life, on July 4, 1802.

Austin Roe, like Caleb Brewster, achieved the rank of captain and carried that title proudly for the rest of his life. He and his wife, the former Catherine Jones, had eight children; in 1798, the family moved from Setauket, on the north shore of Long Island, to Patchogue, almost exactly opposite on the southern shore, and opened a hotel. Unlike many of the other Culpers, Roe enjoyed sharing stories of his spying adventures with locals and patrons at his inn, though he was careful to protect the privacy of his fellow ring members. He passed away on November 29, 1830, at the age of eighty-one.

Benjamin Tallmadge married Mary Floyd, daughter of Major General William Floyd, a signer of the Declaration of Independence. The couple moved to Connecticut, where they had seven children; in 1792, Tallmadge was appointed postmaster for the town of Litchfield. He would later serve sixteen years in the House of Representatives (1801�17). Interestingly, in January 1817, one of the final matters Tallmadge undertook as a congressman before leaving office was to campaign against granting a pension to the three men (John Paulding, Isaac Van Wart, and David Williams) who first captured John Andr�. According to a popular weekly circular of the time, Tallmadge argued that the men were hardly heroes, despite their public image, but were, in fact, �of that class of people who passed between both armies, as often in one camp as in the other.� His objection was rooted in the fact that �when Major Andr�s boots were taken off by them, it was to search for plunder, and not to detect treason.�.�.�. If Andr� could have given to these men the amount they demanded for his release, he never would have been hung for a spy, nor in captivity.� Tallmadge died on March 7, 1835. He was eighty-one years old.

Robert Townsend never spoke of his service, never applied for a pension, never corrected those who assumed he had done nothing but tend his shop during the war, and never, it seems, recovered emotionally from the blow of Agent 355�s capture and imprisonment. After the war he grew even more reserved and reclusive. Dr. Peter Townsend, the son of his brother Solomon, took a particular interest in his somber, silent uncle Robert and often asked him about his service during the war, but the older man was tight-lipped and shared very little. Townsend kept to himself, staying near his brothers and their families but never marrying himself, though he may have fathered a child with his French-Canadian housekeeper in the years following the war. The child�a large, blond, blue-eyed boy who resembled all the Townsend men except the slender, dark Robert�was named Robert Townsend Jr. by his mother, Mary. There was some suspicion that another Townsend brother, the flirtatious William, the �flower of the family,� who happened at that time to share a house with Robert, was actually the father. But Robert, having no other children, took responsibility for the boy�s education and welfare; his will includes bequests for his supposed son, several nephews, and a niece. Townsend developed strong abolitionist beliefs and staunchly opposed any type of slave ownership; later in life he worked on behalf of some former slaves of his father�s to help them gain their freedom. The man once known as Culper Junior died exactly three years after Benjamin Tallmadge, on March 7, 1838, at the age of eighty-four.

Abraham Woodhull married Mary Smith in 1781. He spent the rest of his life in Setauket, where he raised three children and served in roles of authority in the Suffolk County government. He never spoke much about his role in the spy ring. Mary died before Abraham; Lydia Terry became his second wife in his final years. He passed away on January 23, 1826, and was buried in the Setauket Presbyterian Church graveyard. In 1936, the Mayflower Chapter of the Daughters of the American Revolution erected the following marker near his simple headstone:

Friend and confidant of George Washington, Head of the Long Island Secret Service During the American Revolution he operated under the alias Samuel Culper, Sr. To him and his associates have been credited a large share of the success of the Army of the Revolution. Born in Setauket Oct. 7, 1750 in the original Woodhull homestead, son of Richard W. & Margaret Smith. Fifth generation from Richard Woodhull, the original grantee of a large portion of Brookhaven Town. He was a Presbyterian, occupying a �Pew of Authority� in the old church and doing much toward the building of the new church. He was a man of integrity punctual and precise in his business relations. He freed his slaves long before they were legally free. He filled numerous important positions being Magistrate in Setauket many years, Judge of the Court of Common Pleas 1793�1799, First Judge of Suffolk Co. from 1799�1810.

Agent 355, whose name and whose fate have both been lost to time, might have escaped imprisonment and gone on to live a long and happy life. Or she might have passed away somewhere in the dark, disease-infested hull of HMS Jersey. When the British left New York in November 1783, they abandoned the Jersey in the harbor, with several thousand starving prisoners still on board.

It is extremely difficult to learn much at all about the lives and deaths of those unlucky enough to have been captured. After the surrender of the British, the former colonists sought to piece together their shattered lives and homes; many records were lost, destroyed, or simply filed away without any thought to their deeper significance. Thousands of individuals were missing from battlefields, prison camps, and prison ships; thousands more were untraceable due to emigration, desertion, or simply westward movement into the newly opened territories beyond the Appalachians. In the mid-nineteenth century, as the generation who lived during the Revolution was passing away, historians made some efforts to reconstruct lists of inmates� names by interviewing survivors of the Jersey. Though quite rare (and, since they were recalled several decades after the fact, not wholly reliable accounts), women�s names do appear on some of these lists; none have yet been proved to be that of Agent 355.

���������

For generations, the only Revolutionary War spy immortalized in history books was the brave but ultimately unsuccessful Nathan Hale. Tales of the Culper Ring were relegated to local legend or mystery (who was Culper Junior?). Learning the true identity of Washington�s most consistent and valuable spy in the one city the general valued most was a pursuit undertaken by several prominent researchers, who analyzed the oral traditions and followed up on hunches. Townsend was always among those considered likely contenders, but the spy could not be unmasked until the �wagon full� of his letters was found in 1929 and given over to the care of Morton Pennypacker, who compared the writing with that of surviving Culper letters. At last a much more complete story of the ring could be told.

This momentous discovery was made during a dark and uncertain time in American history. The Great Depression threatened the very fabric of the nation, then all eyes were focused on the upheaval in Europe and the creeping threat in the Pacific. The United States was poised at the brink of its next great chapter and was not concerned with rewriting history. Despite Pennypacker�s efforts to shine a light on these provincial heroes of Long Island, Manhattan, and coastal Connecticut, the Culpers once again sank into obscurity. But even if their story was not known across the nation, the fruits of their labors, their letters, and their lives were�and continue to be�felt from sea to shining sea in the freedoms and independence all American citizens enjoy.

We knew the story of the Culper Ring was important. We knew it was a story whose characters and events should be standard fare in history classes across the country. But what we didn�t know was how relevant it still proves today within the intelligence community of the United States.

In February 2012, we were granted access to CIA Headquarters in Langley, Virginia, where we met with the agency�s chief historian.

Outside the building is a statue honoring Nathan Hale�s courage and patriotism; inside the building are exhibits on various spying operations of the past. But nowhere did we find homage to the Culper Ring�until we sat down for our meeting.

We were stunned to learn that the history of the ring is taught as part of the introductory training for new agents. Whether suggested by Washington or Tallmadge, or simply figured out, through bravery and intelligence, on their own, the methods used by these citizen-spies�the dead drops, the well-crafted backstories, the compartmentalizing of intelligence, the secret encrypted code�are many of the same methods still used today by secret agents the world over.

And like the courageous men and women of our modern covert services, the Culpers worked in profound secrecy. They never sought credit, never received accolades, and never revealed the risks they took or the sacrifices they made to serve our country. Under the unblinking leadership of Benjamin Tallmadge, Washington�s secret six served a newborn nation against a military that was considered to be unbeatable. The observation of Major George Beckwith bears repeating: �Washington did not really outfight the British, he simply outspied us!�

In this book, we have included photographs of some of the places, portraits, and humble graves that bear silent testimony to our nation�s first and most accomplished ring of clandestine operatives.

There are no statues of these brave souls, whose feats should earn them a place of honor alongside the heroes of the Revolution. It is our sincerest hope that Robert Townsend, Abraham Woodhull, Caleb Brewster, Austin Roe, James Rivington, and Agent 355 will be given their rightful place in American history. Their extraordinary heroism and patriotism, unknown to their contemporaries, should not be forgotten. George Washington wouldn�t have wanted it any other way�after all, he preserved their letters among his belongings, and it is because of him that we know their story.

The page numbers in this index refer to the printed version of this book. The link provided will take you to the beginning of that print page. You may need to scroll forward from that location to find the corresponding reference on your e-reader.

abolitionism, 212

Adams, John, 3, 195

Agent 355, xvii, 97, 123, 135, 144�46, 149, 213, 216

Andr�s possible connection with, 94, 117, 146

as covert agent, xviii, 87

possible capture of, 177�78, 211

speculation as to identity of, 93�94

Townsend and, 87, 165, 173, 177�78, 211

American Revolution, 11, 36

Anderson, John, see Andr�, John

Andr�, John, 85�86, 97, 108, 117, 127

Benedict Arnold and, 134�38, 144�46, 151�61

capture and execution of, 160�61, 163�73, 175, 185, 187, 211

Peggy Shippen Arnold and, 86, 131�32, 134

Appalachian Mountains, 16, 117, 193, 213

Arnold, Benedict, xv, 86

Andr�s capture and, 160�61, 163�64, 166�68

in British army, 179�80, 185

as British spy, 134�39, 141�46, 151�53, 155, 219

courtship and marriage of Peggy Shippen by, 132�33

Culper Ring and, 142�43, 161, 164, 173, 175�81

in England, 190

escape by, 167�68

insecure and resentful nature of, 127�28, 129, 133, 145, 169, 173

money troubles of, 129, 130, 133, 136�37

new command sought by, 127

in Philadelphia, 127, 130�34, 136�38, 189

plots to recapture, 180�81

West Point command of, 137�39, 142, 146, 149, 154�56, 159�61

Arnold, Edward Shippen, 136, 168, 173, 190

Arnold, Margaret Mansfield, 128�29

Arnold, Margaret �Peggy� Shippen, 131�34, 136, 145, 168, 173, 190

Andr� and, 86, 132, 134, 144

as Loyalist, 86, 131, 138

Atlantic Ocean, 16, 70, 77, 119

Bailey, Nathan, 134

Beckwith, George, 216

Black Rock, Conn., 210

Blackstone, William, 134

Bolton, John, see Tallmadge, Benjamin

Boston, Mass., 17, 37

British expelled from, 3, 5, 13

Boston, Siege of, 5, 21

Boston Massacre, 17, 128�29

Boston Tea Party, 17, 131

Brest, 121

Brewster, Anne Lewis, 209

Brewster, Caleb, xvii, 58, 66, 91, 93, 148, 206, 216

character and personality of, 55�57

as courier, 102, 123�24, 177

naval and shipbuilding reports of, 60�61, 135

postwar life of, 209�10

with Second Light Dragoons, 182, 186

Tallmadge ferried by, 64

Bridgeport, Conn., 210

Britain, British:

American independence granted by, 197

attacks on women by, 48�49

Brooklyn captured by, 10�11

counterfeiting scheme by, xv, 103�6, 142

expelled from Boston, 3, 5, 13

France�s rivalry with, 120

in French and Indian War, 15�16

Hudson River patrols of, 151�52

intelligence system of, 185�86

Long Island occupied by, 1, 3, 27, 31, 49, 56, 59, 73, 75�76, 110, 135, 136, 142, 187

naval codebook of, xv, 189�90

New York occupied by, xvi, 3, 13�14, 15, 19�20, 28, 34, 43�44, 49, 73�75, 93, 110, 113, 126, 127, 132, 134, 139, 145�46, 157, 177, 180, 185, 187, 191�93, 194�99

Philadelphia abandoned by, 34, 130, 132

prison ships of, 38

spies of, 125

Tallmadge�s camp raided by, 89�90

Washington trapped in Brooklyn Heights by, 11

British army, 26, 27, 102

Brookhaven, 35, 204, 212

Brooklyn, 7, 10, 26, 73

port of, 122

strategic importance of, 81�82

Brooklyn, Battle of, 15, 37, 43, 74

Brooklyn ferry, 46, 188

Brooklyn Heights, 10�12

Brown, John, 129

Buchanan, Thomas, 74

Buchanan family, 71, 74, 77

Bunker Hill, Battle of, 36�37, 60

Canada, 192, 197

Caribbean Sea, 16, 128, 188

Carleton, Sir Guy, 191�92, 195�96, 200

Central Intelligence Agency, 215

Champe, John, 180�81, 185, 219

Charleston, S.C., 117, 191, 195�96

Chesapeake Bay, 152, 185

Chester, John, 37

Clinton, Henry, 7, 85, 91, 117, 119, 123�25, 127, 141, 147, 154, 177, 181, 185, 189�92

Andr�s capture and, 170�73

Arnold and, 134, 136�37, 139, 143, 145, 170

Concord, Mass., 36

Connecticut, 4, 12, 37, 42, 45, 49, 51, 65, 93, 110, 112, 123, 129, 138, 145, 147, 166, 176, 183, 211, 214

militia of, 21, 129

Tallmadge in, 53, 56, 57, 64, 82

Connecticut�s Continental Line, 37

Continental Army, 4, 8, 11, 18�20, 22, 27, 33, 35, 64, 77, 130, 132, 135, 143, 167, 170�71, 182, 192, 197

impact of British counterfeiting on, 103�4

Townsend and, 73�74

Continental Congress, 5, 37, 176, 197

Arnold charged reparations by, 136�37

First, 18, 131

mint of, 104

Second, 7, 18, 131

Cornwallis, Charles, 189, 190

counterfeiting, xv, 103�6, 142

Coventry, Conn., 20

Cow Boys, 156�57

Cresswell, Nicholas, 43

Croton River, 157

Culper, Samuel, Junior, see Townsend, Robert

Culper, Samuel, Senior, see Woodhull, Abraham

Culper Ring, xv�xviii, 58, 82, 87, 102, 138, 141, 186�88, 194, 197�98, 222�23

Arnold and, 142�43, 161, 164, 173, 175�81

code used by, 90�92, 94, 107

compared with Arnold and Andr�, 134�35

invisible ink used by, 62�67, 90, 96�97, 99, 114, 134, 148

letters of, 222

postwar lives of, 209�14

relative obscurity of, 213�14

return of, 122�24, 126

revocation of, 122, 127

taught in CIA training, 215�16

timeliness of reports of, 109�12, 116, 119

Townsend�s resignation and, 115

Washington�s postwar visits with, 205�7

Currency Act, 17

Custis, George Washington Parke, 202, 210

Danbury, Conn., 60

Deausenberry, John, 113�14

Deausenberry family, 112�14

Declaration of Independence, 7, 43, 73, 107, 131, 211

DeLancey, Oliver, 185�86, 188

Delaware, 130

Devil�s Belt, 93

Diehel, Daniel, 115�16

Dobbs Ferry, N.Y., 151, 159

Duchess of Gordon, 106

East Hampton, 61

East River, 42, 100

England, 62, 86, 105, 106, 172, 185, 193, 210

Enlightenment, Age of, 36

Entick�s Spelling Dictionary, 91

Erskine, General, 61

espionage, eighteenth-century perceptions of, 69

Estaing, Jean-Baptiste-Charles-Henri-Hector d�, 121

Europe, 214

trading with, 71

Exp�dition Particuli�re (Special Expedition), 121

Fairfield, Conn., 182, 209

farmers:

British occupation and, 47

gentleman, 59

in Hudson Valley, 45

merchants and, 44�45

smuggling by, 45�46

fishermen, smuggling by, 45�46

Florida, 16

Floyd, Mary, 211

Floyd, William, 211

Floyd family, 85

Flushing, 61

Fly Market, 74, 203

Fort Knyphausen, 81

Fort St. George, 182, 185

Fort Ticonderoga, 129

France, 77

as American ally, 221

Britain as rival of, 120

cryptography in, 91

Franklin in, 34, 120

in French and Indian War, 15�16

troops sent by, xv, 117, 119�22, 124�26, 141�42, 147�48

Franklin, Benjamin, 34, 77, 120, 195

Franks, Major, 166

Fraunces Tavern, 203

French and Indian War, 15�16, 17, 29, 34, 70, 128

George III, king of England, 4, 7, 11, 17, 19, 25, 42, 43, 49, 62, 84, 120, 131, 133, 145, 193, 196

Georgia, 8, 18, 191

Germans, see Hessians

Germantown, Pa., 39

Grasse, Fran�ois-Joseph-Paul de, 124, 188, 190

Graves, Admiral, 124

Great Depression, 214

Greene, Nathanael, 170

Hackensack, N.J., 28

Hale, Nathan, 20�25, 31, 34, 36, 213, 215

execution of, 1, 3, 26�27, 30, 33, 38, 58, 172, 193, 219

Halifax, Nova Scotia, 6, 83, 195

Hamilton, Alexander, 26, 124, 148, 153, 165�68

Hancock, John, 38

Hard Winter, 11

Harlem, 81

Harlem River, 81

Hartford, Conn., 165

Haverstraw Bay, 157

Hawkins, Jonas, 60, 90, 92, 100

Henry, Patrick, xvi, 18

Hessians, 10�11, 27, 29�30

Higday, George, 89�90

Honeyman, John, 29�31, 126

Hooper, William, 107�8

Horn�s Hook, 81

House of Representatives, U.S., 211

Howard, William, Jr., 9�10

Howard, William, Sr., 9�10

Howe, Robert, 143�44, 156

Howe, William, 28, 86, 107

New York as goal of, 5�6, 8, 10, 12

Hudson River, 6, 109, 112, 142, 146, 151, 157, 167

Hudson Valley, 4, 45, 62, 136, 191

Huntingdon, Francis Hastings, tenth Earl of, 48

Huntington, N.Y., 65

Huntington, Samuel, 176

Intolerable Acts, 18, 131, 180

invisible ink, 62�67, 90, 96�97, 99, 114, 134, 148, 221

Iredell, James, 107

Jamaica, 61

Jamaica Pass, 9, 12, 37, 74

Jameson, John, 160�61, 163�64, 167, 170

Jay, James, 62, 63, 221

Jay, John, 62, 195

Jefferson, Thomas, 18

Jersey, HMS, 178, 213

Jewish settlers, earliest, 185

King�s Bridge, 187

King�s College (Columbia University), 62

Knowlton, Thomas, 20�23

Lafayette, Marquis de, 121, 142

Langley, Va., 215

Laurens, Henry, 195

Lee, Henry, 18, 180�81

Lexington, Mass., 36

Lexington and Concord, fighting at, 18, 36, 73

Litchfield, Conn., 211

Lloyd�s Neck, 122

London, 17, 86, 190�91, 202

Long Island, xv, xvi, 9, 34, 35, 41, 48, 50, 66, 69, 78, 81, 82, 85, 93, 96, 100, 102, 122, 148, 176, 178, 186, 188, 198, 214

British occupation of, 1, 3, 27, 31, 49, 56, 59, 73, 75�76, 110, 135, 136, 142, 187

deteriorating state of affairs on, 60

fighting on, 74

Hale on, 1, 20, 21, 23�26, 38

impact of Revolution on, 47�49

Loyalists on, 21, 25�26, 56, 75, 103, 182, 205

luxury goods and, 45�46

Patriots on, 52

Scott�s missions to, 58

ships and shipbuilding on, 60�61, 189

smuggling on, 45

troop movements on, 142, 147�48

Washington�s tour of, 205�6

Woodhull�s reports on, 59

Long Island militia, 37

Long Island Sound, 42, 46, 47, 57, 62, 82, 93, 112, 123, 147, 177, 182�83, 209

privateers in, 65�66

Louis XVI, king of France, 34, 120

Loyalists:

Buchanan family as, 71, 77

emigration to England and Canada by, 192�93, 197

Hale and, 20�21, 25�26

on Long Island, 21, 25�26, 56, 75, 103, 182, 205

masquerading as, 112�14

in New York, 9, 42�43, 84�87, 93�94, 144�45, 153, 185, 191, 195

Peggy Shippen Arnold as, 86, 131

in Philadelphia, 131, 134�35

postwar concerns for spies who masqueraded as, 199�201, 202

Rivington�s spying among, 107�8, 177, 189�90, 220, 222

luxury goods, 45�46, 72

McLane, Allen, 130, 189

Manhattan, xviii, 1, 6, 7, 9, 10, 26, 34, 61, 87, 93, 139, 198, 206, 214

Andr� in, 85�86

British capture of, 23, 31, 43�44, 73�74, 117

�Holy Ground� district in, 72�73

Patriot-held, 11�12

Townsend in, 72�73, 74�77, 79�82, 83�85, 106, 146�47, 149, 178, 186�88, 202, 224

Underhill boarding house in, 42, 46, 48, 57, 66, 67

see also New York, N.Y.

Mary (housekeeper), 212

Maryland, 9, 28

Massachusetts, 4, 6, 8, 17

fighting at Lexington and Concord in, 18, 36, 73

Patriot victories in, 5

Massachusetts Committee of Safety, 129

Mastic, N.Y., 182

Memoirs of the War in the Southern Department of the United States (Lee), 180

mid-Atlantic region, 27, 73

Montreal, 77

Montresor, John, 26

Morristown, N.J., 115

Mount Sinai, N.Y., 182

Mount Vernon, 202�3

Mulligan, Hercules, 115�16

Narragansett Bay, R.I., 122

Navy, French, 122, 188�90

New Brunswick, N.J., 28, 30, 197

Newburgh, N.Y., 197, 200

New Hampshire, 8

New Haven, Conn., 128, 130, 138, 169

New Jersey, 7, 27, 28, 110, 152, 180

New London, Conn., 21

Newport, R.I., 121, 125, 141

Newtown, 61, 82

New York, N.Y., 50, 90, 100, 105, 106, 115, 122, 123, 131, 152, 156, 177, 189, 210

Arnold in, 176

British in, xvi, 3, 13�14, 15, 19�20, 28, 34, 43�44, 49, 73�75, 93, 110, 113, 127, 132, 134, 136, 139, 145�46, 157, 177, 180, 185, 187, 191�93, 194�99

as British target, 5, 9

British withdrawal from, 199�201, 213

Culper letters from, 110�11

fashionable society in, 93�94

Loyalists in, 42�43, 84�87, 93�94, 144�45, 153, 185, 191, 195

merchants in, 45

strategic importance of, 5�7, 97, 190, 223

Townsend in, 80�82

Washington�s decision not to attack, 124�26, 182�83

Washington�s inauguration in, 205

Washington�s plans to recapture, 20, 85, 117, 119, 124, 147, 188, 191, 193�96

see also Manhattan

New York General Assembly, 70

New York Harbor, 3, 6, 38, 56, 93, 124, 125, 193, 197

New York Provincial Congress, 73

New York State, 27, 71, 73, 166

need for spy ring in, 33�34, 49�50, 120

northern, 77, 129

upstate, 138

North Carolina, 71, 107�8, 191

North Castle, 160�61, 164

North River, 100

Nova Scotia, 197, 202

Ohio River, 16

Oyster Bay, N.Y., xvi, xvii, xviii, 27, 61, 66, 67, 70, 74�75, 76, 85, 152, 205, 222, 224

Pacific Ocean, 214

Paris, negotiations in, 195�96

Park of Artillery, 26

Parliament, British, 17�18, 128, 131

opposition to American war in, 190�91

Patchogue, N.Y., 210

Patriots, xvi, 4, 5

Paulding, John, 158�60, 211

Pennsylvania, 7, 27, 28

Pennypacker, Morton, xv�xvii, 214, 222

Philadelphia, Pa., 4, 7, 28, 33, 39, 84, 86, 94, 104

Arnold in, 127, 130�34, 136�38, 189

British army�s abandonment of, 34, 130, 132

Continental Congress in, 18, 131

Loyalists in, 86, 131, 134�35

prison ships, 178

privateers, 65�66

prostitution, 48�49, 72�73

Providence, R.I., 4

Putnam, Israel, 60

Quakers, 72

Quebec, invasion of, 136�37

Queens County, 74

Queens County Militia, 74

Queen�s Rangers, 66�67, 75, 110, 152

Rall, Johann, 29�30

Rawdon, Lord, 48, 220

Revere, Paul, xvi

Rhode Island, 121, 124, 141

Rising Sun Tavern, 39

Rivington, James, xvii, 78, 84�85, 96, 117, 131, 205, 216

as American agent, 105�8, 177, 189�90, 220, 222

coffeehouse of, 85, 86, 135

Washington and, 202, 210

Robinson, Beverly, 154

Rochambeau, Count Jean-Baptiste Donatien de Vimeur de, 121

Rockaway Path, 10

Rodrigue Hortalez & Company, 120, 221

Roe, Austin, xvii, 9, 56�58, 60, 90, 93, 96, 123, 148, 177, 188, 216

postwar life of, 210�11

tavern of, 66, 135, 206, 211

Roe, Catherine Jones, 210

Roosevelt, Theodore, xvii

Ross, Betsy, xvi

Royal Gazette, 84�85, 86, 105�8, 199

Royal Navy, British, 8, 12, 56�57, 121

movements of, 111, 135, 195

Sackett, Nathaniel, 33, 34

Salem, Conn., 168

Saratoga, Battles of, 130

Savannah, Ga., 121, 191

British departure from, 192

Scott, Charles, 34, 50, 52, 58

Second Continental Light Dragoons, 38�50, 152, 168, 182

Second Partisan Corps, 180

Setauket, N.Y., xviii, 35, 46, 57, 62, 66, 70, 82, 90, 95, 111, 182, 186, 206, 210

Setauket Presbyterian Church, 212�13

Sheldon, Elisha, 152, 168

Shippen, Margaret �Peggy,� see Arnold, Margaret �Peggy� Shippen

Simcoe, John, 61, 66�67, 75�76, 77, 110, 152, 206

Smallwood�s Regiment, 28

Smith, Joshua Hett, 154�58, 175

social class, 92�93

Sons of Liberty, 17, 84, 210

Southampton, N.Y., 61

South Carolina, 117, 127, 191, 196

Spain, Florida held by, 16

Stamford, Conn., 23

Stamp Act, 17, 128

Stamp Act Congress, 17

Staten Island, 7, 8, 19, 48, 109, 115, 220

Strong, Anna Smith, 93

Strong, Selah, 93

Suffolk County, 35

Sugar Act, 17, 128

Supreme Court, U.S., 107

Sutherland, Captain, 154

Tallmadge, Benjamin, 55, 83, 206, 223

Andr�s capture and, 160�61, 163�65, 168�70, 172�73

Arnold and, 169, 178�79

on Arnold as risk to Culpers, 176�79

background and education of, 35�37

British raids on camp of, 89�90

as chief of intelligence, 58

code developed by, 90�93

concern for postwar safety of spies by, 199

Culper Ring commanded by, xvii, 57, 60, 80, 94, 109�11, 114�16, 215�16

Hale and, 21�22, 37

on New York return, 201�4

postwar life of, 211, 212

return to Long Island by, 204�5

and Second Continental Light Dragoons, 35, 38�40, 168, 182�83

Townsend�s delivery to, 193�94

Washington and, 119, 123

Woodhull and, 89, 114, 122, 124, 147�49, 183, 186, 192, 198, 222

Woodhull recruited by, 49�53, 56

Woodhull�s anxieties and, 64�65, 67, 102�3

Tallmadge, Benjamin (father), 35, 37�38, 204

Tallmadge, Samuel, 52

Tallmadge, Susannah Smith, 35

Tallmadge, William, 37�38

Tallmadge, Zipporah Strong, 37

Tallmadge family, 70

Tappan, N.Y., 172

taxes on American colonists, 17, 45, 128

Teller�s Point, 153

Templeton & Stewart, 72

Townsend, James, 112�15, 119

Townsend, Peter, 211

Townsend, Robert, 69, 71, 74�77, 91, 201, 202, 216, 220, 224

Agent 355 and, 87, 165, 173, 177�78, 211

on Andr�s death, 172�73

on British counterfeiting, 104�5

British impressment of, 192

character and personality of, 71�72

concerns in wake of Arnold�s escape, 176�79, 182

Continental Army and, 73�74

identification as �Culper Junior� of, xvi�xvii, 214

postwar concerns of, 199�200

postwar life of, 211�12

recruitment of, 77�80

resignation of, 115

resumption of spying by, 123�24

Rivington and, 105�8

spying career of, 83�85, 89, 94�97, 100�102, 112, 114, 135, 146�47, 149, 186�88

Washington on, 80�82, 94�96, 111, 176�77, 206�7

Westchester delivery to Tallmadge by, 193�96

Townsend, Robert, Jr., 211�12, 220

Townsend, Samuel, xvii, 70�74, 79

arrest of, 74

British occupation of home of, 75�76, 110, 152, 206

Townsend, Samuel, Jr., 71

Townsend, Sarah, 70, 72

Townsend, Solomon, 71, 74, 77, 211

Townsend, William, 71, 212

Townsend family, xvi�xvii, 70, 71�72, 76�77, 110, 205, 220, 222

Treaty of Paris, 16, 199

Trenton, N.J., 27, 29, 126

Trumbull, Jonathan, 37

Tryon, William, 99, 106

Underhill, Amos, 42, 46, 57

in Culper Ring, 101�2, 110

Underhill, Mary Woodhull, 42, 46, 48, 66

Valley Forge, Pa., 34, 40, 131

Van Wart, Isaac, 158�60, 211

Villefranche, Chevalier de, 142

Virginia, 8, 18, 28, 34, 58, 181, 185, 189�90, 203

Vulture, HMS, 153�56, 168, 177

Wallabout Bay, 178

Washington, George, 1, 3, 38, 43�44, 56, 73, 79, 89, 91, 104, 145, 148, 200�201, 212, 215

Arnold and, 133, 137�38, 141�42, 146, 152�53, 163�73, 179�81

and Battle of Trenton, 29�31

as commander in chief of Continental Army, 18

counterintelligence by, 125�26

decision not to attack New York, 124�26, 182�83

departure for Mount Vernon by, 203�4

departure from Massachusetts by, 4

as first president, 205

in French and Indian War, 15�16

Hale and, 19�20, 23�27, 58

headquarters of, 124

Honeyman�s spying and, 28�31

invisible ink and, 62�63, 65

and Jamaica Pass mishap, 9�10

Lafayette and, 121

letters of, 28�29

Long Island attack reconsidered by, 182�83

Long Island toured by, 205�6

march to New York by, 6

New York City as goal of, 20, 85, 117, 119, 124, 147, 188, 191, 193�96

New York defended by, 7�9, 11�12

Pennsylvania campaign of, 34

return to New York City by, 199, 201�3

at Second Continental Congress, 18

Simcoe�s failed attempt to capture, 110

speed of Culper operations criticized by, 109�12, 120, 122

spy network of, xv�xvi, xviii, 15, 19�20, 27, 30�31, 33�35, 40, 49�52, 57, 59, 60, 67, 80�83, 94�97, 99�100, 101�2, 107, 109, 114, 115�16, 135, 141, 186, 193�96, 216, 219, 222, 223

on Townsend, 80�82, 84�86, 111, 176�77, 206�7

in Yorktown, 189�91

Washington, John, 28

Washington, Samuel, 28

Westchester County, N.Y., 193�96

West Indies, 83, 121, 129, 195

Westminster Abbey, 172

West Point, xv, 94, 137�38, 142, 146, 149, 152�56, 160�61, 164�65, 175

Wethersfield, Conn., 36�37

White Plains, Battle of, 38

White Plains, N.Y., 51, 156

Whitestone, 124

Williams, David, 158�60, 210

Wolsey, John, 65�66

Woodhull, Abraham, xvii, 41�42, 44�46, 48, 75, 91, 93, 104, 110, 135, 138, 197�98, 206, 216

anxieties of, 59�61, 64�66, 102�3, 111�12, 123

Brewster recruited by, 55�58

British officers quartered in home of, 64�65

invisible ink and, 62�67

postwar life of, 212�13

on replacement spies, 116

Roe recruited by, 56�58

Simcoe�s pursuit of, 66�67

Tallmadge and, 89, 114, 122, 124, 147�49, 183, 186, 192, 198, 222

Tallmadge�s recruitment of, 49�53, 222

on Townsend, 177�78, 186

Townsend and, 83, 89, 96, 100�103, 187�88

Townsend recruited by, 77�80

on Washington�s revocation, 122

Woodhull, Adam, 41�42

Woodhull, Lydia Terry, 212

Woodhull, Margaret Smith, 212

Woodhull, Mary, see Underhill, Mary Woodhull

Woodhull, Mary Smith, 212

Woodhull, Nathaniel, 10, 37, 41, 74�75

Woodhull, Richard V. (brother), 41�42

Woodhull, Richard W. (father), 66�67, 75, 76, 212

Woodhull, Susannah, 42, 46, 50

Woodhull family, 70

Yale College, 20�22, 35, 36, 128, 169

Yorktown, Battle of, 188�91, 220

captured British codebook in, xv, 189�90

Young, Israel, 106