Washington's Spies

by Alexander Rose

The Culpers, Senior and Junior, were not exaggerating. In recent months, as part of their beefed-up intelligence apparatus, the British had established new checkpoints, were sending out more frequent patrols, and had recruited dozens of informers. Mostly owing to Hiram’s tips, they were already aware that an intelligence network was operating in New York, passing through Setauket, and from there it wasn’t difficult to guess that Tallmadge—who the British knew, thanks to Arnold, was its manager—was arranging transport across the Sound. The British secret service wanted to roll it up.

  Tallmadge himself had noticed the reinvigorated efforts of the enemy: In early April, he reported, British intelligence had adopted a “regular system” to “open a more effectual communication with the disaffected in this state [Connecticut]. Chains of intelligence, which are daily growing more dangerous, and the more injurious traffic [across the Sound], which is constantly increasing, are but the too fatal consequences, which this system is calculated to promote.”29

  One of the men responsible for these “chains of intelligence” was Colonel Joshua Upham. A former Massachusetts Loyalist turned colonel of dragoons and aide-de-camp to Sir Henry Clinton, he had recently been placed in charge of the Lloyd’s Neck whaleboatmen, who had rebuilt the camp outside Fort Franklin that Tallmadge had destroyed in September 1779 and were busy disrupting communications across the Sound as part of the British plan to unsettle the Culpers. Being well acquainted with De Lancey, Upham was also involved in a bit of spying. In June he sent “two refugees of fair character” to Connecticut to see “several friends to Government [i.e., British] who reside in that country”; they brought back news of four French divisions having left Rhode Island, the first proceeding to Danbury, and the second and third to Hartford (the destination of the fourth was unknown). “Their object,” he wrote, “is universally believed by the rebels, and friends of government to be New York.” Upham’s intelligence, which was accordingly filed in De Lancey’s Intelligence Book, was substantially accurate: Rochambeau was moving his troops in order to participate in Washington’s scheme to surround a Loyalist corps at Kingsbridge in combination with an attack on Fort Washington from the New Jersey side of the Hudson.30 Indeed, two weeks after writing that letter, Upham reported that about 450 French troops had landed about two miles away from Lloyd’s Neck, and had marched, rather foolishly, to within four hundred yards of his twelve-pounders. Upham stoutly put the enemy to a “disgraceful retreat” by firing grapeshot at them, leaving the “grass besmeared with blood.” His men were, said Upham gloatingly, “in the best spirits imaginable.”31

  Given its importance to British whaleboating, morale, and intelligence operations, Tallmadge determined to wipe this nest out—again. It would not be such an easy touch this time around. Now there were alert soldiers guarding the promontory, and the navy had provided a sixteen-gunner, two small frigates, and a galley as a defensive screen for the docked whaleboats. About eight miles away, there were another 140 armed men, so ruling out a flanking assault. Tallmadge’s daring scheme envisaged simultaneously sweeping the Sound with his flotillas of whaleboats to draw off the navy while up to twenty skilled pilots would land several hundred of his dragoons and artillery pieces on Lloyd’s Neck in a proto-D-Day.32 Washington backed the plan, but stipulated that it “must depend, on the absence of the [main] British Fleet, the secrecy of the attempt, and a knowledge of the exact situation of the enemy.”33

  The last, at least, was quickly resolved. Woodhull sent a “faithful person” (i.e., Captain Woodhull) who, he was careful to say, “knows not the smallest link in the [Culper] chain” but was knowledgeable about “armies and fortifications,” to survey the positions, and he confirmed that “the number of men at Lloyd’s Neck is certainly not more than 500 nor less than 400 fighting men.”34 Fortunately for Colonel Upham, wrote a disgruntled Tallmadge, “the British fleet have returned to New York” from an oceangoing cruise, and he was obliged to postpone the assault.35 Washington suggested he talk to Rochambeau about providing French warships to attack the fleet in the harbor, but owing to their naval commitments elsewhere, Tallmadge eventually concluded that it was “impossible to put the plan proposed in evolution at this time.”36 So that was that. In the end, Colonel Upham, along with General Arnold, launched a major raid on New London, Connecticut, that coming September. Upham, who always relished a good skirmish with the rebels so long as the odds were heavily in his favor, said that “everything required was cheerfully undertaken and spiritedly effected by the party I had the honor to command.”37

  In the meantime, Tallmadge attempted to restore the Culper Ring on a stronger footing, financially speaking. Washington, too, had noticed that their irregular reports had been very “vague and uncertain” in recent months, and told Tallmadge that he was “fully impressed with the idea of the utility of early, regular, and accurate communications” from them once again. To this end, Washington belatedly authorized “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),” but stipulated that in return “their exertions should be proportionably great.”38 This was easier said than done, given improved British security. As Woodhull told Tallmadge on May 8 after a trip to New York, “I can only obtain verbal accounts for you and that but seldom, as the enemy have lately been made to believe that a line of intelligence is supported here. They are jealous of every person that they may see from this part.”39 Worse, Townsend was still adamant that he would not set pen to paper for fear of interception, and though Woodhull and he “racked our invention to point out a proper person” to copy down Townsend’s nuggets and compose the intelligence letters, “no person will write.” By May 19, Woodhull himself had become too antsy to continue for much longer, since the “enemy have got some hint of me for when passing at Brooklyn Ferry was strictly examined and told some villain supported a correspondence from this place. I do assure you am greatly alarmed—and wished to be relieved from my present anxiety. I shall not think it safe for me to go to New York very soon—and can only supply you with verbal accounts as hath been the case for some time.” The only positive note was struck by Woodhull’s mentioning that Austin Roe was willing to work occasionally as a courier, but Tallmadge realized that in itself wouldn’t be enough to save the Ring.40

  Instead, Tallmadge began mooting the possibility of using temporary spies, or agents who were willing to pass information on occasionally and lived for short periods on Long Island. So long as they reported just once or twice before returning to Connecticut, their chances of being caught, he believed, were less than that of permanent agents-in-place. The downside, of course, was that they could not be trusted as implicitly as the Culpers, nor would they be willing to work just for expenses. Most of these temps, it turned out, were acquaintances of Brewster’s. In mid-May, Tallmadge noted to Washington that if Townsend couldn’t be tempted back into the game, he would “send a person from this side (a native of Long Island) to engage another person, entirely independent of C.[ulper] and who lives much [closer] to New York.”41 The “native of Long Island” was Brewster, and his contact was the pseudonymous “John Cork,” who was paid six guineas to go into New York on several occasions and see what he could find. Nothing more is known of him, not even his real name.42

  An agent known as “S.G.” was also recruited by Tallmadge, again through Brewster, in the same month. He was, Tallmadge told Washington, “a person heretofore unknown in my private correspondence, but from whom I should expect important services if he could be engaged in this way.”43 “S.G.”—probably one George Smith—seems to have acted as a replacement for Brewster whenever the latter was away on his Tory-hunting missions, and was in service as late as August 1782, when Tallmadge mentioned that he had “repaired to Fairfield, and effected an interview with S.G. [and] forwarded, by him, similar instructions to S.C. Senior and Junr.”44 Given the Culpers’ unwillingness to deal with contacts unfamiliar to them, he was likely one of Brewster’s l
ongtime deputies aboard the whaleboats.

  Another was Nathaniel Ruggles, a schoolmaster and physician born in 1713 and educated at Yale, who had helped arrange accommodation and subsistence in Connecticut for Whig refugees from Long Island at the beginning of the war.45 Brewster and Tallmadge evidently persuaded him to do some secret service work on the side, and he was placed temporarily at Old Man’s, an isolated spot a few miles east of Setauket, in the spring of 1781. From there he visited New York several times. His cover was blown within months, thanks to the testimony of Ebenezer Hathaway, a Loyalist captain of the privateer Adventure.

  On April 7, while cruising off Huntington, Hathaway’s boat had been surprised by a flotilla of seven whaleboats and his crew taken prisoner. They were transported to the Simsbury Mines, a former copper mine converted into a nightmarish subterranean prison in Connecticut—the American equivalent of the British prison ships. The captives were led through a series of trapdoors with iron bars progressively deeper underground. At the last one, they climbed down a six-foot ladder, which led to another grate covering a three-foot-wide hole sunk into solid rock that the guards told them led to a “bottomless pit.” The men “bid adieu to the world” and descended down more ladders another eighty feet or so where they discovered “the inhabitants of this woeful mansion.” Down there, the other prisoners were using pots of charcoal to dispel the foul air, aided by a narrow ventilation shaft bored from the surface. Hathaway and his friends stayed there for twenty days, and plotted to break out. On May 18, when twenty-eight of the prisoners were brought upstairs to what passed for a kitchen to cook, they cracked the lock to the grate connecting the kitchen with the ladder leading to the guardroom. At 10 p.m., the grate above was unlocked by the sentries, who were allowing in one of the prisoners’ wives, and Hathaway and his accomplice, Thomas Smith, seized the opportunity to barge their way into the guardroom, where they scuffled with the two soldiers on duty. Hathaway was wounded in three places before the rest of the prisoners could rush through. After that, they surprised the remaining twenty-four guards, who were sleeping, and took them captive before pushing them into the black hole below. Seizing their arms and ammunition, they dispersed and made their way as best they could back to Long Island or Westchester.

  When Hathaway reached New York, he contacted Major De Lancey with information that one of the prisoners, “Clarke”—no first name was ever mentioned—had told him when they were both locked up. Clarke was a whaleboatman of no fixed allegiance who had plundered both sides but had “frequently come over with Brewster” to Long Island. He doesn’t seem to have been a member of Brewster’s regular crew for conveying the Culper dispatches, but was probably used as a stand-in during the opening months of 1781. According to the record of Hathaway’s June debriefing in the British intelligence archives, he said “that one Nathaniel Ruggles who lives at Setalket [sic] sends over intelligence once every fortnight by Brewster who comes from Connecticut and lands at the Old Man’s. Ruggles comes to New York frequently.” After his escape, Hathaway, moreover, had originally landed on the northeastern shore of Long Island, where, on his way to New York, he met “Major Talmadge,” who was “purchas[ing] clothing for the rebel army.”46

  William Heron had first mentioned Brewster and the Setauket connection back in February, and the British now had a name and an address (though not Woodhull’s)—as well as confirmation that Tallmadge was still operating. Ruggles, however, doesn’t appear to have been arrested, most likely because he had scarpered back to Connecticut. Ruggles was unaware that his near-neighbor, Abraham Woodhull, was an agent—Tallmadge was too canny to let that slip—but had the British captured him, they might have mounted an ambush for Brewster and Tallmadge next time they arranged a rendezvous with Ruggles. At that point, all it would have taken to scoop up Woodhull was someone recalling the gossip from June 1779 about the unassuming Setauket farmer being involved with dubious activities on the Sound, or someone remarking that Austin Roe was in New York an awful lot for a tavern-keeper. It wouldn’t have taken long to link Woodhull to Roe to Townsend.47

  It was the greatest of luck, then, that at that moment Woodhull—as a result of the increased British activity and perhaps also due to Tallmadge’s warning him that he had seen Hathaway, who was supposed to be in prison—quit. I “live in daily fear of death and destruction. This added to my usual anxiety hath almost unmanned me,” he wrote on June 4. “I dare not visit New York myself and those that have been employed will serve no longer, through fear.” He was “fully persuaded by various circumstances and observation” that if he continued the correspondence “regular without any interval” his “ruin” would be assured, “and it appears clear to me that it would be presumption to take one step further at present.” No longer, he felt, could he “expect that protection from Heaven that have hitherto enjoyed. You must acknowledge and readily conclude that have done all that I could, and stood by you when others have failed, and have not left you in the darkest hour but when our affairs appear as clear as the Sun in the Heavens, and promiseth a speedy and I hope a happy conclusion.”48

  Woodhull was soon tempted back into the Ring on an ad hoc basis by that old faithful, Tallmadge.49 But he never again played a central role in Washington’s deliberations, and the same can be said for the rest of the gang. The Culper Ring had done its job well and had served with great valor, but they were amateurs overtaken by the rapid evolution of espionage: From 1781 onwards, a new breed of spy had emerged, men like William Heron whose allegiances and motives were distinctly murky. They were agents who lacked the simple patriotic virtue of Benjamin Tallmadge, Abraham Woodhull, Anna Strong, and Captain Nathan Woodhull, the bravery of Robert Townsend and Hercules Mulligan, the doggedness of Caleb Brewster and the two couriers Austin Roe and Jonas Hawkins. The Culper Ring’s day was almost over, and that of the professional, the cynic, and the mercenary was dawning.

  Thus, in the preparations for the showdown with Lord Cornwallis at Yorktown, and the subsequent winding down of the war, the Culper Ring are virtually invisible. Beginning in the summer of 1781, Woodhull’s letters became steadily more infrequent, while Tallmadge occupied himself with more purely military matters (he was seconded to Rochambeau for a time) and Washington was focused on calming an army restless for payment after the great struggle and the peace negotiations in Paris.50 Between June 1781 and April 1782, for instance, Woodhull wrote not a single letter, even though Townsend continued to submit the occasional verbal report. The former’s reticence was prompted by his betrothal to a local lass, Mary Smith, on November 24, 1781: No longer a single man, had he come to grief, Mary, as the wife of a traitor and a spy, would have lost everything.51 When Woodhull did finally write, it was to convey a happy event. He reported directly to Washington on May 5, 1782, that “a cessation of arms is ordered, to take place within these lines both by land and sea—and terms of peace are given to Congress, but the conditions is here unknown, but generally supposed independence is offered.” He also warned that “the enemy still continue to fortify, nevertheless, both on York and on Long Island. I have nothing further to inform you of but hope soon to have peace in our land.”52 By any lights, Woodhull’s intelligence was a scoop: Official news of British acceptance of independence reached New York only in August. “The inhabitants of York & loyal refugees are very much hurt at this sudden change of affairs, saying that their loyalty to their King and Mother Country, has sold them, & made them worse than slaves,” wrote Captain William Feilding, a British officer in New York, to the Earl of Denbigh.53

  In the spring of 1782, perturbed by British activity in New York under the new “Commander-in-Chief of His Majesty’s Forces between Nova Scotia and the Floridas”—Sir Guy Carleton—when they were expected to be preparing to evacuate, Washington temporarily reactivated the Ring, whose members proved willing now that imminent victory had greatly reduced the risks of being executed if caught.54 Having dispatched Austin Roe to reconnoiter British positions, and after receiving a report fro
m Townsend, Woodhull soon wrote that

  At York Island they are encamped from the City to the bridge, and fortifying on the banks of the rivers near the City and it is expected they will contract their lines and only attempt to defend a part of York Island near the town if they should be attacked. They have a number of ships ready to sink in the river if an enemy should appear. There’s only two ships of any consequence in the harbor, the Lion and Centurion. Their design appears only to act on the defensive and be as little expense to the Crown as possible. God grants their time may be short for we have much reason to fear within these lines that Carleton’s finger will be heavier than Clinton’s.… He is called a tyrant at N. York by the inhabitants in general and makes them do soldier’s duty in the City without distinction.55

  While Carleton informed him on August 2 that the new Whig administration in London had accepted the principle of American independence, given Woodhull’s account of British activity, Washington was not quite ready to drop his guard. “From the former infatuation, duplicity and perverse system of British policy, I confess I am induced to doubt every thing, to suspect every thing,” he cautiously confided to General Greene.56

  On August 10, Washington instructed Tallmadge that he found “it very important, from a variety of considerations, to have the most definite and regular information of the state of the enemy at New York, which can possibly be obtained; particularly with regard to the naval force which now is in that harbour, or shall be there in the course of the summer or autumn.” Since he had gone “to the southward last campaign,” the general desired Tallmadge to utilize “the channel of intelligence through the C——s … to keep me continually and precisely advised of every thing of consequence that passes within the enemy’s lines.” He understood that “the only great difficulty has been in the circuitous route of communication,” but urged yet again “the greatest diligence and dispatch.”57