Washington's Spies

by Alexander Rose

  He was glad his intelligence had been helpful, but Woodhull was beginning to doubt his own fortitude. His lack of education, poor hand, and provincial manners caused Woodhull embarrassment, particularly whenever he compared himself to Tallmadge, whose time at Yale and his membership in the elite officer corps had bestowed a gracefulness and social ease lacking in his less privileged friend. “Whenever I sit down I always feel and know my inability to write a good letter,” wrote Woodhull at one particularly low moment. “As my calling in life never required it,” he continued, feeling ever more forsaken, “and much less did I think it would ever fall to my lot to serve in such public and important business as this, and my letters perused by one of the worthiest men on earth.”6

  Realizing that his man was liable to crack up, on April 16 Tallmadge sailed with Brewster to Setauket to reassure Woodhull that Washington was properly appreciative of his efforts. Owing to “a violent storm and contrary winds,” as well as the unexpected decision by a couple of British officers to billet themselves on Woodhull, Tallmadge was forced to hide in the woods near Woodhull’s house for five days. Whenever Woodhull sneaked food to him, the two old friends talked of ways to relieve the pressure. Woodhull was grateful for the fifty guineas Tallmadge brought with him, so at least his monetary concerns were sated, but Woodhull was adamant that if Washington wished him “to discontinue his present correspondence he will most cheerfully quit.” However, while Woodhull was as eager as Washington to find a faster route, he worried that safety would be sacrificed for speediness. After much discussion, Tallmadge succeeded in persuading Woodhull to accept the possibility of having a man, personally vouched for by him but accepted also by Woodhull, on Staten Island “who will receive his dispatches and forward them at all times.” But Woodhull stipulated that the man must “go across with a boat to an appointed place [in Manhattan]” to receive his letters. Under no circumstances would Woodhull go to Staten Island.

  From Woodhull’s point of view, this was a perfectly reasonable demand. Already taking an enormous risk traveling and staying in New York, there was no reason why Woodhull should be asked to assume another one talking his way past the sentries at the ferries (what business did a Setauket farmer have on Staten Island that required his presence there every two weeks?), and entering the maw of one of the most heavily guarded strongholds in British America—just to meet a contact unknown to him. He wanted to at least have the chance to walk away if he noticed anything untoward about the Staten Island agent when he landed at Woodhull’s chosen “appointed place,” presumably at one of the quieter wharves. In Washington’s eyes, however, Woodhull was asking the impossible. How was he to find an agent on Staten Island who would pass muster by Woodhull when he didn’t even have a permanent one in New York?

  The Staten Island proposal died soon after, much to Washington’s annoyance, for no solution had yet been found to accelerate transmission of the letters to him.7 As it was, Woodhull continued to insist that, as Tallmadge put it, “any instructions which your Excellency may wish to communicate to Cr. you will please to forward to me as usual, no other person being appointed in this quarter with whom he would be willing to correspond.” Jonas Hawkins, to make matters worse, cut back on his duties around this time, halving the number of couriers available and placing the entire burden on Austin Roe’s shoulders.

  Hoping to moderate Washington’s ill temper about his picky spy, Tallmadge did pass on an anecdote, culled during his involuntarily prolonged sojourn in Setauket, that illustrated just how jumpy Woodhull had become. It seems, having received a vial of the stain and being “much pleased” with it, Woodhull sat down to write a dispatch. No sooner had he finished it, but “suddenly two persons broke into the room (his private apartment). The consideration of having several [British] officers quartered in the next chamber, added to his constant fear of detection and its certain consequences made him rationally conclude that he was suspected, and that those steps were taken by said officers for discovery. Startled by so sudden and violent an obtrusion he sprang from his seat, snatched up the paper, overset his table and broke his vial. This step so totally discomposed him that he knew not who they were, or even to which sex they belonged—for in fact they were two ladies who, living in the house with him, entered his chamber in this way on purpose to surprise him. Such an excessive fright and so great a turbulence of passions so wrought on poor C. that he has hardly been in tolerable health since.” The two young ladies were actually, it seems, his mischievous nieces.

  A few days later, Woodhull’s spirits were hardly improved when, on his way to New York, he was mugged near Huntington and was glad to escape with his life. Tallmadge suspected the villains (“I know the names of several”) were local privateers who had taken to landing on Long Island “and plunder[ing] the inhabitants promiscuously.”8

  Worn to a frazzle, Woodhull went on almost complete hiatus throughout May, but early June proved almost as hazardous to his health as had April. Writing from Setauket, Woodhull related to Tallmadge on June 5 that John Wolsey, a Long Islander privateer based in Connecticut, had been captured by the British. In order to secure his parole, Wolsey told his captors that while in Connecticut he had overheard—perhaps while one of Brewster’s men was blabbing in a tavern—that Woodhull was up to something dubious. On his return to Long Island, Wolsey “lodged information against me before Col. Simcoe of the Queens Rangers.”

  John Graves Simcoe, a jowly Old Etonian and Oxonian born in 1752, was a junior officer in the Thirty-fifth Regiment of Foot when he arrived in Boston in 1775, but had bought a captaincy within the year and was wounded three times during the New York and New Jersey campaigns of 1776–77. On October 15, 1777, he was promoted to colonel of the Queen’s Rangers—Robert Rogers’s old outfit—and began turning it into a first-class line regiment, a far cry from the old days.9

  Simcoe, “thinking of finding me at Setauket came down,” but “happily I [had] set out for N. York the day before his arrival, and to make some compensation for his voyage he fell upon my father and plundered him in the most shocking manner.” On his return, Woodhull’s life was saved only by pleading with “a friend of mine” who contacted a general’s adjutant and stood guarantor for Woodhull’s Loyalist credentials. Nevertheless, “I am very obnoxious to them and think I am in continual danger.”10

  Woodhull’s anonymous but well-connected “friend” was Colonel Benjamin Floyd (1740-1820), a well-meaning, gullible Loyalist militia officer who preferred the solitude of Setauket to campaigning. He was the younger brother of Colonel Richard Floyd, a rebel-rousing Tory militant, and the two of them were cousins of William Floyd, the high Patriot who signed the Declaration of Independence. They were also distantly related to Woodhull through the late General Woodhull’s wife, Ruth Floyd (William’s sister).11

  Owing to his ravages of Patriot property, Richard was a popular target of raiders from Connecticut—Caleb Brewster particularly disliked him—suffering them at least thrice, each time “his cattle, sheep, and several of his slaves” being kidnapped. (The British had a contradictory, politically calculated relationship with slavery: They freed slaves owned by rebels, but did not liberate those owned by Loyalists; they freed runaways who joined the army or served as auxiliaries, but not those unable or unwilling to; they stopped the slave trade, but continued to allow female slave auctions and sold blacks captured in enemy uniform. Thus, while it was British policy to promise, as Clinton did in 1779, “every negro who shall desert the rebel standard, full security to follow within these lines any occupation which he shall think proper,” this decree did not apply to slaves already living in New York.12 It was a distinction that caused much jealousy between the enslaved, upright maids serving in rich merchants’ houses and the free, but unlettered, farmhands newly arrived from the southern plantations.)

  As for Colonel Benjamin, he periodically suffered plundering by his own side. Judge Thomas Jones, the acerbic Tory, recalls that in September 1778, Governor Tryon and General De Lanc
ey marched two thousand soldiers and several battalions of militia to eastern Long Island to expropriate cattle belonging to rebel sympathizers. On the way, they stopped at Setauket and dined with Floyd. During supper, their “soldiers robbed him of all his apples, his Indian corn, potatoes, turnips, cabbages, the greatest part of his poultry, and burnt up all his fences.”

  Very soon after, the hapless Floyd was again plundered—this time by “a party from New England” who “took away his furniture, and robbed him of £1,000 in cash”—and was “carried to Connecticut.”13 Immediately afterwards, Woodhull successfully implored Washington to release Floyd from imprisonment and allow him to return to Setauket. This secret intercession was not prompted by personal regard for Floyd, but because “I am very likely to stand in need of his services.”14 Woodhull had already recognized the utility of having a well-placed—if unwitting—protector.

  Thanks to his foresight, Woodhull, for the moment, was safe, but “I dare say you will be filled with wonder and surprise, that I have had the good fortune to escape confinement. And am sorry to inform you that it hath rendered me almost unserviceable to you.” As “I am now a suspected person I cannot frequent their camp as heretofore,” continued Woodhull, and therefore “I [propose] quitting 10 [New York] and residing at 20 [Setauket].” To cushion the blow, Woodhull added, “I shall endeavour to establish a confidential friend [in New York] to step into my place if agreeable.” Once done, “most probable I shall come to you [in Connecticut]. And shall wish to join in the common defence.”15 In truth, Woodhull was not keen on leaving his parents and his farm to join the army, but if his cover were blown, he would end up dead if he remained on Long Island.

  If it had to be, it had to be. “Should suspicions of him rise so high as to render it unsafe to continue in New York,” agreed Washington, “I should wish him by all means to employ some person of whose attachment and abilities he entertains the best opinion, to act in his place.” It was a pity about Woodhull, but Washington thought his replacement, if one could be found, might be more receptive to “a mode of conveying [his intelligence] quickly,” a matter he still regarded as being “of the utmost importance.”16 What Washington didn’t know was that Woodhull already had his eye on a New York connection. And that Woodhull, his natural patriotism prevailed upon by Tallmadge and against his instinct to flee to Connecticut, would stay in Setauket to act as the new agent’s handler.

  Three days after offering to resign, Woodhull traveled to New York—for the last time, he expected and hoped—to “settle the plan proposed.” He soon reported that “my success hath exceeded my most sanguine expectations.” While there, Woodhull had “communicated [his] business to an intimate friend and disclosed every secret and laid before him every instruction that hath been handed to me; it was with great difficulty I gained his compliance, checked by fear.” This “intimate friend” was “a person that hath the interest of our country at heart and of good reputation, character and family as any of my acquaintance. I am under the most solemn obligation never to disclose his name to any but the Post [Austin Roe, by this time] who unavoidably must know it.” He “will expect an ample support, at the same time he will be frugal. As long as I am here shall be an assistant and do all that I can.”17 Washington was most pleased with the acquisition, and sent Woodhull ten guineas to cover the money he had lost being mugged.18

  At last, Washington and Tallmadge had a man in New York. The chain of agents Tallmadge had envisaged in the summer of 1778 was complete. The New York man would gather intelligence, compose his letter in invisible ink and code, and pass it to the courier at a prearranged time and place. The courier (Austin Roe) rode from New York to Setauket, and transferred the letter to Woodhull—either giving it to him in person or, for safety’s sake, dead-dropping it in a buried container in one of Woodhull’s fields—who would add his own letter containing observations, as well as information given to him by Roe. Then he would signal or arrange with Brewster to land outside town for the pick-up. Brewster took the package across the Sound and gave it to Tallmadge, who usually developed the letters, added his own gloss and comments, and handed all the messages to a dragoon for conveyance to Washington’s headquarters.

  The new agent was Robert Townsend—soon unimaginatively aliased “Samuel Culper, Junior” and bestowed the code number “723.” A secretive, reserved man who found it difficult to form permanent attachments, Townsend remained a lifelong bachelor. He kept his spying activities so much to himself that even the nineteenth-century Townsend family history, which might otherwise be expected to laud him to the skies, contains precisely one unremarkable sentence on the man called Culper, Jr.: “Robert, son of Samuel, died unmarried, March 7, 1838.”19

  His anguished mind writhed with contradictions. He was a man of parts and halves in a time of wholes and absolutes. Half Quaker, half Episcopalian, partly secular, partly devout, somewhat idealistic, somewhat mercenary, Townsend was neither wholly pacifist nor entirely militant. He was an American who refused to fire a musket for his country, a Loyalist who struggled against the British.

  Woodhull knew Townsend, then in his late twenties and from Oyster Bay (in western Long Island), because, owing to the shortage of accommodation in New York, Townsend also happened to lodge at Amos Underhill’s boardinghouse. Underhill was not only Woodhull’s brother-in-law but was also descended from the founder of Oyster Bay, Captain John Underhill, whose Quaker family still lived there. Townsend was probably directed to Amos’s house by one of Underhill’s Oyster Bay relatives. One can imagine how Woodhull, over the years, slowly warmed to Townsend over the dinner table or at a local tavern as they repeatedly bumped into each other staying at the Underhills’.20 Robert’s father, Samuel Townsend, a local politician of Whiggish bent, was well known the length and breadth of Long Island, and Woodhull no doubt knew, or was made aware, that Robert was one of his boys. Robert, in turn, would certainly have mentioned to Woodhull that he had served for a time under the command of his kinsman the late General Nathaniel Woodhull.

  Always cautious about approaching possible recruits to his Ring for fear of betrayal, Woodhull gently sounded out this man with a sterling Patriot background, but one so innocuous he had slipped under the British radar. To all intents and purposes, Townsend was a Loyalist, but he, too, found he could trust Woodhull, another secret Patriot. Eventually, in early June 1779, Woodhull asked whether Townsend was interested in serving his country. Townsend was in.

  Unlike Woodhull, Brewster, and Tallmadge (as well as Roe and Hawkins), who were stout Presbyterians with broadly similar backgrounds and whose motives for spying ranged from the adventurous (Brewster) to the vengeful (Woodhull) to the purposeful (Tallmadge), Townsend was a solitary creature prone to bouts of depression, insomnia, and guilt. Despite his “excellent symptoms of health,” Townsend, for instance, slept but “middling well,” and would spend much of one year “sunk under a low depressed and dejected state of mind.”21

  From his surviving papers emerges a learned, troubled man. Possessing a large library of the standards every gentleman was expected to own—Locke’s philosophical tracts, Boswell’s Life of Samuel Johnson, Montesquieu’s works, the opera omnia of Chaucer—and having a weakness for Alexander Pope, trade magazines, and current-affairs journals from London, Townsend’s habit was to jot down meaningful passages from them, sometimes adding his own comments and criticisms.22 Two of these in particular bear witness to his peculiar temperament and tricky predicament. For him, it was evident that “a gloomy and melancholy disposition is … a vice or imperfection; but as it may be accompanied with [a] great sense of honour and great integrity, it may be found in very worthy characters; though it is sufficient alone to imbitter life, and render the person affected with it completely miserable.” Townsend’s decision to spy was motivated partly by his desire to lighten his “gloomy and melancholy disposition” with a labor requiring “great integrity.”

  Townsend, who maintained a number of dual identities—Loyalist and Pa
triot, Anglican and Quaker—that forced him to condemn what he felt was right, was keenly aware of the distinction between public display and private opinion. “The gravest persons,” he wrote, “betray an inward esteem for a statesman, who has been the contriver of a very notable piece of political management, at the same time they are … obliged outwardly to censure the immorality of the action.”23 Individuals, in other words, must often say one thing while doing another, sometimes something wicked, and sometimes merely questionable—like spying.

  Luckily, we have a single, fragile portrait of Robert Townsend. His nephew Peter took up sketching about Christmas 1812, with Robert being one of his very first sitters the following January. It is a small charcoal picture—amateurishly executed, with thick lines and a clumsy pose—glued into a sketchbook, of a formally dressed, bespectacled Townsend in a chair, reading a book. It is a great pity that Peter drew his beloved uncle so early, for in the years to come, thanks to practice and three months’ worth of lessons with one Archibald Robertson of 79 Liberty Street, he developed into a fine artist. The good news is that several distinct family similarities—present but un-evolved in the rudimentary Robert portrait—can be seen in Peter’s excellent sketch of Robert’s sixty-five-year-old sister, Sarah, done twelve years later, as well as in other pictures of the Townsend family. As does her brother, she wears small round glasses perched on a long, aquiline nose; she has high, prominent cheekbones, thin, downturned lips, a firm chin, and an oddly wide space between the upper lip and the nose. Like other Townsends in Peter’s sketchbook, Robert has a towering forehead, a slim, even spindly, figure, and short, curly dark hair.24

  The Townsends were among the first to cross the water from New England and settle on Long Island—when most of it was still Dutch territory—but were relatively recent arrivals in Oyster Bay. In 1645, John Townsend was one of the patentees of Flushing, and he moved to Jamaica in 1656. Both Flushing and Jamaica were towns in what would become Queens County (which would encompass what is today the Borough of Queens and adjacent Nassau County), and John’s descendants never left its confines. Samuel Townsend—John’s great-great-grandson and Robert’s father—originally conducted business from Jericho, but in 1740, when he was twenty-three, he bought a six-acre property in nearby Oyster Bay. Over the next three years, carpenters built a white wooden mansion—dubbed Raynham Hall, after the Townsends’ ancestral home of Raynham, Norfolk—designed to accommodate Samuel’s growing family.25 An eighteenth-century real-estate agent later described the Hall as “a commodious two-storey house, with four rooms on a floor, situate near the centre of the village on the main road to the Mill, and about 50 rods from the harbour, with a good barn and other outhouses, a well of good water at the door, an excellent spring 20 rods from the house, a good garden [and] a good bearing orchard.”26 In 1743, when the house was completed, Samuel moved to Oyster Bay, and established himself as one of its leading citizens. Within a decade, he had become Justice of the Peace, eventually becoming town clerk.