George Washington's Secret Six

by Brian Kilmeade

  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 André 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.

  A WOLF IN SILK AND LACE

  Peggy Arnold was not the only woman with a secret connected to Benedict Arnold. The whirl of celebration that had died down with the absence of the British top brass from New York now began anew, and Agent 355 found herself once again in the company of New York’s wealthiest Loyalists and most powerful British officers. The gossip was generally unchanged. Many of the well-to-do families of the Northeast were casually connected through intermarriage or business associations of one kind or another. More than one family loyal to King George had a cousin or two serving under General George Washington, nor was it unheard of that a family with one political allegiance should suddenly find itself related to one of the opposite persuasion when members from each decided to wed.

  Therefore, it didn’t seem unusual at all that the Arnolds’ names should come up in conversation that summer. Benedict’s family was established just across the border in Connecticut, and the former Miss Shippen—whose own family was extremely well connected—had been acquainted with many of the officers now in New York. Benedict Arnold’s name might have even been something of a joke, at first, among the British. Here was an overly eager merchant–turned–major general who seemed desperate for praise and for cash—and was willing to go to great lengths for either one. His price changed even as his emotional investment did, and his letters were at once full of self-importance and a kind of panicked need for validation. The officers who despised him may have ridiculed him over their drinks within 355’s hearing.

  By September, however, the snickering would have ceased. Arnold had assumed the command he and General Clinton had both so desperately wanted for him, and no time had been wasted in accepting his terms of surrender. Only a few things were needed now to bring the whole plan to fruition. First, an opportunity to familiarize the British with the plans of the fort so that they could exploit its vulnerabilities and storm it as swiftly as possible and, second, time to get the necessary men and weapons in place to ensure that any resistance the Patriots offered was futile.

  No plans of such a sensitive nature were explicitly discussed in social settings like dinner parties, but certain phrases, pointed glances, and delicious insinuations that something was coming would have abounded among the most senior officers. Red-faced brass chortled, slapping each other on the back and toasting their port glasses to the Hudson River or to West Point itself. When Major André let drop in conversation that he was going north for a few days, anyone who was simply mingling for company, conversation, and culinary delights would have assumed he was attending to routine business. To someone with a more serious mission than simply seeing and being seen, however, something seemed amiss in these veiled hints. What exactly was afoot was unclear, but the lady whose job it was to “out wit them all” would have reported what she had observed.

  TWO WOLVES IN MERCHANTS’ SHIRTSLEEVES

  While his name was being band
ied around New York’s most exclusive circles during his first weeks of command, Arnold was quite busy sending letters. Besides writing to Washington about his desire to increase the provisions and make improvements at the fort and composing letters about his need to learn the identity of spies, Arnold also found the time to send a letter to an American outpost, informing its members that a certain merchant from the city by the name of John Anderson might be passing their way and begging their assistance in helping him to secure safe passage to West Point. Additionally, Arnold was also carrying on his correspondence with André so as to arrange the meeting outside the city that would finalize their negotiations and plans for the handing over of the fort.

  When the long-anticipated meeting finally took place, André was to pose as a prosperous businessman, Arnold as his patron. In keeping with their cover, the men wrote their letters not in the numbered code or invisible ink of their previous exchanges, but very much in the role of a client and a vendor making plans to carry out a large transaction—which, in many ways, they were, though the roles were reversed.

  Townsend, meanwhile, found that when he left his shop to observe the goings-on around Manhattan that September he could not help but notice the uptick in preparations along the docks. The British were clearly fitting ships for some kind of engagement, though Townsend could not be sure if this was merely a response to the arrival of the French fleet and the fear that a naval battle might be brewing, or if it was with some other specific aim. Even the soldiers and sailors with whom he conversed seemed uncertain as to their orders. It seemed unlikely that significant troop movements would be following so closely on the heels of the intentional misinformation regarding Washington’s supposed plans to attack the city and the unanticipated recall of troops. Then again, the blow to Clinton’s pride that incident had delivered may have prompted him to plan an aggressive response simply to prove he would not be made the fool.

  The increase of activity in mid-September was definitely new, though, after a relatively quiet August. Woodhull had written to Tallmadge on September 1: “In regard of the state of affairs in general he [Culper Junior] assured the express they remained as heretofore or as when wrote you last, nothing new, everything appeared to be at a stand, and the enemy much embarissed expecting an attack.” Despite the calm in the city in August, troops had continued to shift around Long Island, and Woodhull had even mentioned that a British spy had crossed the Sound to Connecticut—a man who was “positively an agent for the enemy. He hath been a long time serviceable in that way, and this is his second embassy. I know it to be true and have lately had a perfect knowledge of his conduct for this three years past, and have been solicited by his friend as an assistant.”

  It was worth noting, but hardly earthshaking news. Spies were everywhere, and both sides knew it. That this operative tried to convert Woodhull to his side while clearly unaware as to Woodhull’s true loyalties is both comical and a testimony to the convincing role Woodhull was playing as a man of profound apathy. His secret letters, however, reveal just how deep his passions truly ran. Four days later, Woodhull wrote again to Tallmadge to inform him of a movement of troops away from Setauket, which left the town much more vulnerable to an American invasion to reclaim it: “For God’s sake attack them, you’ll certainly be successful, if you are secret about it. . . . Setauket is exceedingly distressed. Pray offer some relief.”

  No prospect could have delighted Tallmadge more than the possibility of liberating his hometown, and he wrote to Washington to propose just such a raid: “The enclosed Dispatches from Culper have this moment come to hand. . . . C. writes with great sollicitude for troops to be sent from this side to attack those lying at Setauket. I need not repeat to your Excellency how exceedingly happy I should be to assist in such an Expedition, should it be thot. advisable.” To Tallmadge’s disappointment, Washington did not approve the plan, and he would have to wait several more months before he could wage battle on Long Island.

  As the warm weather faded, Townsend continued to submit reports written in invisible ink, which now fell almost exclusively on Tallmadge to reveal and decipher. The job had previously belonged to Washington’s aide-de-camp Alexander Hamilton, while Tallmadge was in charge of making sense of the general intelligence and summary reports Woodhull, Roe, and Brewster compiled. But recently Tallmadge had been tasked with the white-ink letters—perhaps after Washington recognized the urgency of the information conveyed about the French troops—and Tallmadge found himself even more impressed now with the quality and accuracy of Townsend’s reports than he had been before.

  None of them knew, however, just quite what they were in the midst of in September 1780. The reports from the city, the strange behaviors, the activity with the ships—Tallmadge couldn’t put his finger on it, but his instincts told him something was not right. He felt as if he had nearly all the elements in front of him, almost all the clues gathered, but he was not sure what he was looking at or what the picture was that he needed to assemble. That he had letters on his desk from his merchant-spy in New York regarding an officer from New York venturing toward West Point seemed wholly unconnected. Despite all the hints he received from 355, Woodhull, and Townsend, Tallmadge didn’t connect the dots until it was almost too late.

  CHAPTER 13

  The Deal Is Done

  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. André, 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. André 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 André greatly worried that this sudden change would cause him to miss out on the fun. “Rely upon it your alarms are vain,” André 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 Drago
ons 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.

  JOHN ANDERSON SETS FORTH

  The evening of Monday, September 18, witnessed an elaborate dinner party at the home of a well-to-do New York Loyalist. Though it was hosted in honor of General Clinton and his closest officers, special attention was paid to Major André, and it seems to actually have been something of an unofficial send-off for the young man, as he was about to embark upon a mission that, they hoped, would result in one of the greatest victories for the British since the war began.

  The next day André set out northward with the goal of reaching HMS Vulture, a fourteen-gun sloop docked near Teller’s Point, by evening. Because it was a British ship, he arrived not as “John Anderson, Patriot merchant” but as himself, bearing letters from General Clinton that needed to be hand-delivered farther up-country. The crew was ignorant as to the true nature of André’s visit, likely because of their proximity to West Point. Should any sailor let a casual word slip while onshore, the whole deal would be ruined. André boarded the Vulture for the night and awaited a message from Arnold for their meeting the next day. None came.