By August—just a few months after beginning work as a Culper—Townsend was proving himself a difficult agent to run, more difficult even than Woodhull, who, as cell leader, now had to deal with these “human resources” issues instead of Tallmadge. “I have had much discourse with Culper, Jur.,” he complained to Tallmadge. “Contrary to his intimation and my expectation, he continues in business, that engrosseth some part of his time, and interfereth with the important business he hath undertaken.” Though “I have again most earnestly endeavoured and begged him to disengage himself from all concerns that may interfere with the public business he hath undertaken,” Townsend’s “reply in substance was this, that he feared his inability.” Townsend, while “willing to do all he could to serve his country,” would “not leave himself entirely out of the line of business,” his reason being that he would be left “destitute of a support thereafter [in] employment when his services may not be required.” Further, unlike the altruistic Woodhull, Tallmadge, Brewster, and the others, Townsend wanted, like the good merchant he was, a reward commensurate with the risks he was running. “I do not conceive his views are altogether mercenary yet [he] thinks he should have some compensation,” concluded Woodhull, “but his chief aim is to have such a recommendation at the close of this war as will entitle him to some employment” or commission to public office under the new, postwar American government.17 In his defense, Townsend claimed that he had originally intended to quit his business, but now could not, “owing to my having a partner”—Henry Oakham.18
Washington, playing Solon and Solomon as master of the Culper Ring, pondered the matter. On September 24, 1779, judgment was handed down. First, Woodhull must tell Townsend that he “may rest assured of every proper attention being paid to his services” after the war. Second, “it is not my opinion that Culper Junr. 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 derive 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.”19 His answer satisfied all parties.
Over the next several months, the Culper Ring honed its expertise and its members grew accustomed to working with each other. There were also a few personnel changes. Jonas Hawkins, the Ring’s original messenger, having been only tangentially involved for some time, retired in September 1779. Whereas in April 1779, for instance, Woodhull listed both Hawkins and Austin Roe as the Ring’s messengers, by July, Tallmadge had not bothered giving Hawkins a code number (Roe got 724) in his Code Dictionary, and on August 15, Woodhull, in an encrypted dispatch, was obliged to spell out his name: “Dqpeu Beyocpu [italics added] agreeable to 28 met 723 not far from 727 & received a 356.” (“Jonas Hawkins agreeable to appointment met Culper Junior not far from New York & received a letter.”)20 His final mission in September was botched when Hawkins claimed it was too risky to come into New York. Forcing the annoyed merchant to expose himself by meeting him “at a place quite out of danger on Long-Island,” Townsend testily told Tallmadge he believed Hawkins’s fears were “merely imaginary” and accused him of “timidity.”21 It seemed clear that the once-courageous messenger was too burnt out, too jittery, to continue in the business. Hawkins was out, most likely voluntarily, but also because Townsend refused to work with him: in his very first letter, Townsend had said he was unsure about the content of Hawkins’s character. In his place, Austin Roe became the Ring’s sole, permanent messenger—except when Woodhull himself traveled to New York.
Townsend was being far too harsh on poor Hawkins. A month earlier, as Woodhull recorded, Hawkins had been forced to destroy one of the letters when he faced capture by enemy troops, and these days, he continued, “every house is opened at the entrance of New York and every man is searched.” It was simply too dangerous to convey letters not written in the sympathetic stain because—owing to the recent raid on Tallmadge’s camp—“they have some knowledge of the rout our letters take. I judge it was mentioned in the letter taken or they would not be so vigilant.”22 Indeed, in October, Woodhull judged that “it is too great a risk to write with [plain] ink in this country of robbers. I this day just saved my life. Soon after I left Hempstead Plains and got into the woods I was attacked by four armed men, one of them I had frequently seen in N. York. They searched every pocket and lining of my clothes, shoes, and also my saddle, which the enclosed [one of Townsend’s letters] was in, but thank kind Providence they did not find it. I had but one dollar in money about me. It was so little they did not take it, and so came off clear.” Woodhull finished by begging Tallmadge not to “mention this” to any of the others, “for I keep it a secret for fear it should intimidate all concerned here.”23 Hawkins’s caution, it seems, had been warranted.
But thankfully, Woodhull continued, “I do not think [the vigilance] will continue long so I intend to visit New York … and think by the assistance of a 355 of my acquaintance, shall be able to outwit them all.”24 This mysterious “355”—decoded as “lady” in the Dictionary—is mentioned just once in the Culper correspondence. She was Anna Strong, Woodhull’s neighbor and wife of Selah Strong, an active Whig and delegate to the provincial Congress before the war who was currently jailed aboard one of the British prison ships as a suspected insurrectionist. Selah’s mother was Hannah Woodhull, the eldest sister of General Nathaniel Woodhull, making Abraham and him family.25 (Incidentally, Selah’s sister, Susannah, married Benjamin Tallmadge’s father as his second wife.)26
The British, it seems, were not stopping and searching “every man,” as Woodhull put it, but every solitary man, the sort that fit the profile of known spies. But sheer civility might dissuade troopers from stopping, let alone searching, respectable married men traveling to see in-laws with their equally respectable wives—even if that “wife,” namely Anna, happened to be someone else’s masquerading as your own (and was somewhat older than one might expect since she was born a decade before Woodhull). It was a risk, granted, but Woodhull appears to have been let alone, so he did, thanks to his brave accomplice, “outwit them all.”27
That September, Woodhull’s uncle, Captain Nathan Woodhull, then in his mid-fifties and of Whiggish inclination, was also brought into the Ring; like Anna Strong and Amos Underhill, the captain played a subsidiary role, serving only as needed, or when he could. Thus, on September 19, Woodhull records that “Pevbep Yqqhbwmm” (Nathan Woodhull) recently returned from New York and had told him “there’s a council of war holding of all the general officers … [and] that a large number of troops were embarking” aboard transports.28 Two months later, Culper sent a “person” to check out troop positions “betwixt this and Huntington” who consequently submitted a lengthy, specialized report. As Captain Woodhull was a serving officer with the local Loyalist militia, and so took a professional interest in such matters, he was most certainly the unnamed “person” employed for the task.29
Gaining a mole within the enemy’s ranks was a sweet scoop for the Ring, and that fall, there were moves afoot to recruit a still more senior officer in the same militia outfit—Colonel Benjamin Floyd. The idea originated with Tallmadge, who told Washington about Floyd—the hapless Loyalist kidnapped, imprisoned, paroled (on Woodhull’s recommendation), and repeatedly plundered (by his own side, and sometimes by the Americans). Tallmadge thought him ripe for flipping: Rather like Robert Townsend, a former Loyalist disgusted by the abuses perpetrated by the British occupation, Floyd, Tallmadge speculated, might well be disaffected from his masters. “From a long and intimate acquaintance with this gentleman,” Tallmadge reported to Washington, “I believe him to be of more service in the Whig interest in Setauket then every other man in it, tho’ from his family connections I believe he h
as been in favour of Royal Government.”30
That letter was written on November 1. Two days later—and certainly not by coincidence—Washington directed Governor George Clinton of New York to ensure that Floyd would not be robbed again by Patriot marauders. He never laid out his reasons for demanding that “proper measures” needed to be taken “to bring [the perpetrators] to justice, and prevent such acts of violence in future” by these minor miscreants, but if Tallmadge had hopes of enticing Floyd into the business it would not do to alienate him.31
Tallmadge accordingly requested Woodhull to put out feelers and “take all the pains possible to secure Col. Floyd”—only to be refused. Woodhull argued that Floyd had not, despite appearances, permanently changed sides. And, in any case, he had “no love for Col. Floyd, not for no Tory [italics added] under Heaven, but in my present situation am obliged to cultivate his friendship.” For that reason, Woodhull “dare[d] not mention to him what you proposed. I do not doubt that he would be glad to hear it and perhaps keep it entirely secret for his own interests, but yet he would view me with an Evil Eye.”32 Floyd was more useful not knowing Woodhull’s real business and to keep blithely believing that his distant kinsman was an unassuming Loyalist. Cover had to be maintained. It also didn’t help that, as Townsend did Hawkins, Woodhull heartily disliked him. Given Floyd’s connections with senior British commanders, his acquisition would have been a genuine intelligence coup, but Woodhull was right to suspect that he might betray the Ring and be turned into a double agent against them.
The fall of 1779 also witnessed a flurry of instructions from Washington, who remained intent on quickening the speed of communication and improving the expanded Ring’s efficiency in the face of the increased British surveillance.33 Townsend, he suggested, “should occasionally write his information on the blank leaves of a pamphlet; on the first second &c. pages of a common pocket book; on the blank leaves … of registers, almanacs, 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 [invisible] 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.” Alternatively, “he may write a familiar letter, on domestic affairs, or on some little matters of business to his friend at Satauket or elsewhere, interlining with the stain, his secret intelligence or writing it on the opposite blank side of the letter. But that his friend may know how to distinguish these from letters addressed solely to himself, he may always leave such as contain secret information without date or place; (dating it with the stain) or fold them up in a particular manner, which may be concerted between the parties. This last appears to be the best mark of the two, and may be the signal of their being designed for me. The first mentioned mode, however, or that of the books, appears to me the one least liable to detection.”34
This was sound counsel. But in fact Townsend had already hit upon a variation of the book idea. He would purchase a new quire of high-quality paper, write his message on a blank in the secret ink, and then insert the page at a predetermined place, say, the fifteenth sheet from the top.35 Washington’s idea was the better one, and less liable to crossed wires, as Tallmadge complained when he wasn’t told of the prearranged position: He had to waste much of his precious stain swabbing several sheets to see which one contained Townsend’s dispatch.36 Washington’s idea was cheaper as well, since “common pocket books,” old pamphlets, and obsolete almanacs were less expensive in wartime New York than good paper imported from England, especially when Townsend was using an entire quire each time. Townsend agreed to change his method.37
Overall, Washington was most pleased with the Ring’s progress and wanted to establish the Ring on a more “professional” basis. In early October, he summoned Tallmadge for a conference at the Robinson House at West Point.38 Working together, the two composed a lengthy memorandum laying out Culper Senior’s and Junior’s responsibilities.
INSTRUCTIONS
C——r Junr, to remain in the City, to collect all the useful information he can—to do this he should mix as much as possible among the officers and refugees, visit the coffee houses, and all public places. He is to pay particular attention to the movements by land and water in and about the city especially. How their transports are secured against attempt to destroy them—whether by armed vessels upon the flanks, or by chains, booms, or any contrivances to keep off fire rafts.
The number of men destined for the defence of the City and environs, endeavoring to designate the particular corps, and where each is posted.
To be particular in describing the place where the works cross the island in the rear of the City—and how many redoubts are upon the line from river to river, how many Cannon in each, and of what weight and whether the redoubts are closed or open next the city.
Whether there are any works upon the Island of New York between those near the City and the works at Fort Knyphausen or Washington, and if any, whereabouts and of what kind.
To be very particular to find out whether any works are thrown up on Harlem River, near Harlem Town, and whether Horn’s Hook is fortifyed. If so, how many men are kept at each place, and what number and what sized cannon are in those works.
To enquire whether they have dug pits within and in front of the lines and works in general, three or four feet deep, in which sharp pointed stakes are pointed. These are intended to receive and wound men who attempt a surprise at night.
The state of the provisions, forage and fuel to be attended to, as also the health and spirits of the Army, Navy and City.
These are the principal matters to be observed within the Island and about the City of New York. Many more may occur to a person of C. Junr’s penetration which he will note and communicate.
C——Senior’s station to be upon Long Island to receive and transmit the intelligence of C——Junior …
There can be scarcely any need of recommending the greatest caution and secrecy in a business so critical and dangerous. The following seem to be the best general rules: To in-trust none but the persons fixed upon to transmit the business. To deliver the dispatches to none upon our side but those who shall be pitched upon for the purpose of receiving them and to transmit them and any intelligence that may be obtained to no one but the Commander-in-Chief.39
That same month, recognizing the necessity of “establish[ing] a very regular communication with Long Island,” he wrote no fewer than four letters requesting information on British movements and positions. The reason behind Washington’s series of inquiries was that he had heard in late September several reports of the approach of a French fleet under Comte d’Estaing, who had wintered in the West Indies.40 Any uptick in British activity at New York would signal that Clinton, too, knew of d’Estaing’s movements. In the meantime, Washington ordered Generals Sullivan and Gates to ready their armies to march, and began calling up militiamen from Massachusetts (2,000), Connecticut (4,000), New York (2,500), New Jersey (2,000), and Pennsylvania (1,500) as a prelude to coordinating with the French a surprise assault on Clinton. Washington’s ambitious hope was that d’Estaing would approve of “an attempt against New York.”41 As he explained, “New York is the first and capital object, upon which every other is dependant. The loss of the army and fleet there, would be one of the severest blows the English nation could experience.”42
On October 9, a letter from Townsend arrived bearing the worst of news: Clinton’s naval scouts had spotted d’Estaing. As a result, the New York garrison “was much alarmed,” and “all the men of war and a number of armed transports were ordered down to [Sandy] Hook, with several old hulks to sink in the Channel in case d’Estaing should appear. They had also two or three fire ships preparing, and are building a very strong fort at the lighthouse.” Clinton had also taken steps to prevent an amphibious assault from Connect
icut by deploying the Seventeenth Dragoons and the Queens Rangers, as well as a “considerable number” of infantry at strategic points in western Long Island. Washington’s dream of taking New York back was over.43
In any case, even had Clinton remained in total ignorance of d’Estaing’s approach, the New York attack would never have worked—the French admiral had decided to anchor his twenty-two warships and ten frigates off Georgia, instead, to take British-held Savannah in another show of Franco-American amity. His attack on October 9 was a disaster. Against a numerically inferior, but strongly entrenched, foe, d’Estaing and General Benjamin Lincoln suffered nearly 1,000 dead and wounded compared with British losses of 40 and 63, respectively.44 D’Estaing, who had been hurt in the battle, sailed to the West Indies in high dudgeon.
Even before news of the British victory at Savannah had reached New York, Townsend was reporting that his officer friends were saying large detachments of Clinton’s troops had embarked on transports. “It’s generally believed that they are destined for Georgia”—an indication that Clinton was considering sending reinforcements to the South, now beginning to be regarded as Loyalist territory and Washington’s weak point.45 Townsend’s intelligence was accurate, though in this case military scouts sent Washington more detailed information: A regular regiment and a force of light infantry and Grenadiers did sail.46
In the event, Clinton decided against the plan and recalled the reinforcements before they got too far. Instead, he adopted a defensive position in New York as winter drew in. Later in October, Townsend and Woodhull followed up. “The enemy have large magazines of wood and forage and are daily collecting more, particular hay. Some of the [commissaries] of provision say they have enough of all kinds to last 9 months. I believe they have plenty for six months.”47 From his end, Woodhull added that “they have collected nearly all the forage in Queens County and [are] carrying it to Brooklyn; in one word, every preparation is a making for their defence.”48
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