George Washington's Secret Six

by Brian Kilmeade

  Townsend needed a way to move more freely about the city, making inquiries and giving people a reason to trust him. In other words, he needed a cover story, and he found one just down the street in the coffeehouse and print shop of an English expatriate named James Rivington. A printer and a bookseller by trade, Rivington had left England in 1760 over some unpleasantness (most likely having to do with losing his share of his father’s business in horse racing), sailed to America, and opened up a printing shop first in Philadelphia and then later in New York City. In 1773, he started publishing his own newspaper as a neutral press with the tagline “Open and Uninfluenced,” but eventually it began to promote (as did so many newspapers of the era) a very specific and forceful worldview. In Rivington’s case, it was loyalty to King George, a stance that got him hung in effigy by the Sons of Liberty and mocked openly in Patriot writings—gestures that seemed to greatly amuse him.

  Townsend had always had a knack for writing; for all of his natural reserve in speaking, he could be very expressive with a pen, and his meticulous, detailed-oriented nature that had served him well inspecting cargo ships also lent itself to composing interesting letters. Recognizing a perfect cover opportunity, he applied for a job at Rivington’s paper to write the occasional column of local interest. Rivington recognized the quiet shopkeeper from down the street and was happy to take him up on his offer to contribute to the Royal Gazette’s offerings.

  It was a stroke of brilliance on Townsend’s part. He now had the perfect excuse for asking questions, jotting down details, and querying various movements of troops and matériel into, out of, and around the city. What was more, Rivington’s Tory politics would help deflect any suspicion that Townsend might be harboring Patriotic sentiments.

  Townsend found himself quite busy as he adjusted to the work of three jobs: shopkeeper, journalist, and undercover agent. As a solitary man with no family and few friends to distract him, he may have found the new duties a nerve-racking but interesting distraction. His association with Rivington likely introduced new acquaintances to his circle as well, as the prosperous set flocked to the coffeehouse to be seen in such esteemed company as the British officers. If Townsend’s plain, dark clothes set him apart from the fashionable gentlemen and ladies who discussed politics and soirees, military strategy and dinner parties, no one seemed to mind too much.

  Townsend might even have caught sight of a familiar face or two among the coffee-sipping patrons. He might have spotted an old acquaintance from Oyster Bay, or the nephew of a neighbor, or a member of a prominent Long Island family such as the Floyds, or perhaps even one of his own distant cousins. There was no reason for him to fear such recognitions, should they occur, however. His shop was situated just a few yards away and had been for several years, so it was completely natural for him to be found at the coffeehouse, making the acquaintance of all who came through.

  MAJOR JOHN ANDRÉ

  Another, more sinister figure was establishing himself at Rivington’s coffeehouse at the same time as Townsend. The British had wasted no time in developing their own counterspy network. In the spring of 1779, General Henry Clinton had appointed the dashing young major John André as his chief intelligence officer. The major had impressed the general with his wit and savvy when the general arrived in Philadelphia in the early months of 1778. Now, a little over a year after they first became acquainted, Clinton entrusted André with the task of managing the espionage efforts in the colonies, with a specific eye on New York. André and Clinton were well aware that Washington was desperate to retake New York and had to be sending spies there. Eager to intercept Patriot agents, the new intelligence officer set up his headquarters in Manhattan.

  André was one of those individuals who thrive wherever planted. He’d always been a rather worldly man; his father was from Geneva and his mother from Paris, and they had raised him in London, educating him with high hopes for a future in diplomacy. He was fluent in several languages, including English, French, German, and Italian, was a gifted artist, and often composed comical verses much to the amusement of his comrades. He was also famed as a party planner and a social coordinator, having directed and painted many of the sets for a celebratory theatrical event in honor of General Howe’s return to England from Philadelphia. He had been the toast of that city during the occupation, and was rumored to have offered more than just brotherly love to several ladies therein. Among those who were thought to have fancied him was Peggy Shippen, a sparkling teenager from a prominent Loyalist family, who was renowned as much for her graciousness as for her beauty.

  By the summer of 1779, André had moved on to New York and Shippen had recently married a widower named Benedict Arnold, a general in the Continental Army who had gotten to know her when the Americans reclaimed the city the previous year. It was an unlikely alliance given Arnold’s employment and her family’s politics, but one that seemed to delight bride and groom alike. André, for his part, considered New York a step up from Philadelphia, as it was the closest thing America had to offer, in terms of bustle and variety, to his hometown of London. He quickly became a fixture on the social scene, charming all company with his gallant manners and jovial personality, and spending many languid afternoons sipping coffee and trading ideas at Rivington’s shop.

  André found yet another advantage to his patronage of Rivington’s establishment: He now had a willing publisher for his poems. Rivington was happy to publish any doggerel the dashing young Major André sent his way, as even the silly rhymes of such a popular figure were sure to sell papers among the Loyalist set in Manhattan. So it was that the counterspy unwittingly published his poetry next to the columns of his biggest target.

  THE LADY

  It was probably through his newspaper work that Townsend first made the acquaintance of a young female socialite, of whom he informed Woodhull. In his letter dated August 15, 1779, Woodhull recorded that there was a specific “[lady] of my acquaintance” so situated as to “out wit them all.” Her sudden appearance in his letters following the recruitment of Townsend, as well as the fact that Townsend’s ledger shows he and Woodhull met that same day, hints at the fact that she may have been introduced to the ring by Townsend himself. That she was already in Woodhull’s acquaintance indicates that her name, at least, was already known to him prior to that day, perhaps indicating that she or her family were originally from Long Island. But her apparent presence in Manhattan of late meant that she was somehow uniquely positioned to collect important secrets in a cunning and charming manner that would leave those she had duped completely unaware that they had just been “outwitted” by a secret agent.

  But just who was this mysterious woman so perfectly poised to steal such vital secrets? Woodhull was careful not to record her name, offering only a number—355—in the code that was to define the Culper Ring.

  CHAPTER 7

  Creating a Code

  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 prob
ably 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:

  729 29 15th 1779

  Sir. Dqpeu Beyocpu agreeable to 28 met 723 not far from 727 & received a 356, but on his return was under the necessity to destroy the same, or be detected. . . . Thers been no augmentation by 592 of 680 or 347 forces, and everything very quiet. Every 356 is opened at the entrance of 727 and every 371 is searched, that for the future every 356 must be 691 with the 286 received. They have some 345 of the route our 356 takes. I judge it was mentioned in the 356 taken or they would not be so 660.

  Translated, and with a few creative grammatical adjustments required by the reader, the letter conveyed the following message:

  Setauket August 15th 1779

  Sir. Jonas Hawkins agreeable to appointment. Met Culper Junior not far from New York & received a letter, but on his return was under the necessity to destroy the same, or be detected. . . . [There’s] been no augmentation by ship of war or land forces, and everything very quiet. Every letter is opened at the entrance of New York and every man is searched, that for the future every letter must be write [written] with the ink received. They have some know [knowledge] of the route our letter takes. I judge it was mentioned in the letter taken or they would not be so vigilant.

  AGENT 355

  Tallmadge’s code contained a quirk that both reflects its time and offers up clues to a mystery. There are different codes to designate “man” (371) and “gentleman” (237), and “woman” (701) and “lady” (355); thus, there was a kind of commentary upon the social situation of a subject embedded within the code itself. Any mature adult might be referred to with the generic term “man” or “woman,” according to the subject’s sex; however, a “gentleman” in the American colonies was nearly always considered a man who owned land or a considerable amount of property, and was respected as a person of character in his local community. A woman might be referred to as a “lady” if she was of a well-to-do family, or was an accomplished young woman (that is, either literate and educated, or proficient in the arts of domestic leisure such as music, painting, and needlework). In other words, a man or a woman would generally only be referred to as a gentleman or a lady if he or she were of certain means and social standing. Social standing directly affected the quality of information a person could acquire: a washerwoman or a coachman might have been in a position to overhear some kinds of private conversations, whereas an established gentleman or lady might have been introduced to different types of gossip in a dining room, so Tallmadge’s differentiation was strategic.

  In the case of 355 (the “lady” of the Culpers’ acquaintance), her code indicates that she was of some degree of social prominence. Was she Anna Smith Strong, the wife of Judge Selah Strong, a fierce Patriot who was first detained on a British prison ship in New York Harbor, then fled to Connecticut after his release? Local legend has it that Mrs. Strong, who remained behind to manage the house and family when her husband went into exile, used to hang laundry in specific patterns on her line. The Strong estate, situated on a high bluff, would be visible to anyone passing by boat across the Devil’s Belt portion of Long Island Sound. The hanging clothes would appear as just that—wet clothes drying in the sun—to the untrained eye, but to Caleb Brewster, the arrangement of garments and their colors signified different counts of ships and troops, or in which cove it was safe for him to dock his boat, depending on which version of the story one hears. He would then be able to compile this information and pass it on with the Culper letters from New York when he rowed back across the water to meet Tallmadge or his courier in Connecticut.

  While Anna Smith Strong might have played a satellite role in the ring—she was certainly an acquaintance of many of its members—assisting Woodhull, Roe, or Brewster at some point, there is no actual evidence that either she or her laundry ever served their country by gathering or passing along intelligence. It seems quite unlikely that the fortyish housewife, mother, and spouse of a well-known Patriot rabble-rouser would have ventured from Long Island to Manhattan to attend parties where she would have rubbed elbows with the Loyalist elite and gained the trust of high-ranking British officers.

  A much more likely contender would be a young woman living a fashionable life in New York. Though of pro-American sentiments herself, she almost certainly would have been attached to a prominent Loyalist family, either as a freethinking daughter or a cousin or a niece who was staying in the city with her Tory relations. It is therefore possible that 355 was part of the glittering, giggling cluster of coquettes who flocked about Major André as he moved around the city, enjoying the finest food, wine, and company New York had to offer. Some of New York’s brighter blooms were demure and others played coy, but, just as had been the case in Philadelphia, a few found themselves admitted into André’s private chambers and his confidence, too.

  BEYOND LETTERS

  Despite the white ink and the coded communications, Washington knew that the British were growing more suspicious of the mail and that the tiniest details could attract scrutiny. Writing from his headquarters at West Point, New York, Washington sent Tallmadge a letter a
dvising the major on this matter and also suggesting that Townsend not sacrifice his current employment in order to operate full-time as a spy. His cover story, as it stood, protected him far better and allowed him more freedom to gather information than he would have if he focused solely on intelligence gathering. The letter reveals much of General Washington’s thought process concerning espionage, especially in regard to protecting his valued source.

  Head-Quarters, West Point,

  24 September, 1779.

  Sir,

  It is not my opinion that Culper Junior should be advised to give up his present employment. I would imagine that with a little industry he will be able to carry on his intelligence with greater security to himself and greater advantages to us, under cover of his usual business, than if he were to dedicate himself wholly to the giving of information. It may afford him opportunities of collecting intelligence that he could not obtain so well in any other manner. It prevents also those suspicions which would become natural should he throw himself out of the line of his present employment. He may rest assured of every proper attention being paid to his services. One thing appears to me deserving of his particular consideration, as it will not only render his communications less exposed to detection, but relieve the fears of such persons as may be entrusted with its conveyance to the second link in the chain, and of course very much facilitate the object we have in view; I mean, that he should occasionally write his information on the blank leaves of a pamphlet, on the first, second, and other pages of a common pocket book, or on the blank leaves at each end of registers, almanacks, or any new publication or book of small value. He should be determined in the choice of these books principally by the goodness of the blank paper, as the ink is not easily legible unless it is on paper of a good quality. Having settled a plan of this kind with his friend, he may forward them without risk of search or the scrutiny of the enemy, as this is chiefly directed against paper made up in the form of letters.