George Washington's Secret Six

by Brian Kilmeade

  On Thursday, September 21, Arnold received a letter complaining that boats from West Point had fired upon a small vessel traveling to shore under the flag of truce, which was a violation of the terms of war. “Fortunately none of my people were hurt, but the treacherous intentions of those who fired are not vindicated from that circumstance,” Captain Sutherland had written. The note was signed by both the captain and a certain “John Anderson.” André’s likely explanation to Sutherland for the pseudonym was that they could expect an attack should the Americans know that André himself was currently on board; the real reason, of course, was to alert Arnold to his presence on the ship.

  André also wrote a letter back to his command, stating:

  As the tide was favorable on my arrival at the sloop yesterday, I determined to be myself the bearer of your Excellency’s letters as far as the Vulture. I have suffered for it, having caught a very bad cold, and had so violent a return of a disorder in my stomach which had attacked me a few days ago, that Captain Sutherland and Colonel Robinson [Beverly Robinson, at whose home Arnold was staying] insist on my remaining on board till I am better. I hope tomorrow to get down again.

  He also included a private message intended just for General Clinton’s eyes: “Nobody has appeared. This is the second expedition I have made without an ostensible reason, and Col. Robinson both times of the party. A third would infallibly fire suspicions. I have therefore thought it best to remain here on plea of sickness, as my enclosed letter will feign, and try further expedients.”

  That same night, Arnold ordered some boatmen to row to the Vulture under a flag of truce, and to bring back with them a certain gentleman on board. Arnold could not approach the Vulture himself without arousing suspicion, given his rank and current assignment. In his stead, he sent Joshua Hett Smith, a local resident whom he charged with managing the retrieval. One of the rowers, a seasoned old hand, complained when ordered to muffle the oars to disguise their sound, lest a patrol boat find them. “If the business is of a fair and upright nature, as you assure us it is, I see no necessity for any disguise or to seize the veil of night to execute what might be as well transacted in broad daylight,” he grumbled to the general.

  Arnold responded by ordering the crew to carry out their plans as he had charged them, coolly reminding them, “I have the command of the militia of the county for sixty miles around West Point by the order of Congress.”

  The party set out with no further objections and approached the Vulture with the truce flag hoisted. Smith climbed aboard and, after explaining his task and showing his passes to the officers in charge, Anderson was introduced and agreed to accompany Smith back to shore for the meeting. “Very little conversation passed between Mr. Anderson and myself,” Smith later recalled, “excepting trivial remarks about the tide, the weather, and matters of no concern. Mr. Anderson, from his youthful appearance and the softness of his manners, did not seem to me to be qualified for a business of such moment.” But Smith conveyed him back to shore anyway, trusting that General Arnold knew best.

  After introducing the two men—both of whom were dressed in blue coats—Smith was ordered to return to the boat to wait with the crew. This annoyed him somewhat, as he felt he had earned the right to be present for the discussion, given his efforts in bringing the meeting about, but he did as he was told. Some time later, Arnold and his friend returned and the order was given to bring Anderson back to the Vulture, but Smith objected. The men were tired and could not possibly make the trip back to the ship and to shore once again before sunrise, when they were sure to be spotted. He proposed that if the cover of darkness was, indeed, so very important to Arnold that they had best wait until the following evening to venture out again. Arnold conceded the point and Smith opened his home to them for the remainder of the night.

  By morning, it was clear that the rowboat would have had an even more strenuous voyage than previously anticipated. The Vulture was sailing southward, having been fired upon by American guns. André was very anxious about the situation because the longer he remained off the ship and in American territory, the greater his risk of capture. Arnold persuaded him to take advantage of the day, however, and the two rode out, presumably to inspect some of the routes to West Point and plan for the best possible approach by foot soldiers supplementing the attack from the river.

  But as evening drew near, it was evident that André would have no hope of sailing back to New York on the damaged Vulture and would need to return to the city by land instead. “I wish I was on board,” he said with a heavy sigh, looking in the direction of the ship, but he set out toward White Plains on horseback with Smith and a servant accompanying him for the first part of the journey to help him navigate the unfamiliar territory. Smith stopped at several waypoints to converse with the Patriot soldiers stationed along the route, but André kept to himself so that witnesses later recalled little other than that a man with a round, floppy hat and cape fastened tightly around his neck was a member of the riding party. Smith was well known to many of the American militiamen in the area and respected among them because, as one man later noted, “I had heard it frequently mentioned that [American] General [Robert] Howe used to employ Mr. Smith in getting intelligence.” Other American officers held Smith in contempt; at least one suspected him of being a double agent and a few weeks prior had challenged Arnold on his association with the man.

  Whatever the nature of Smith’s character and his later claimed ignorance, he guided André easily through the American territory. Some of the men advised Smith against riding any farther that night, given the patrols in the area. Even if friendly, they might give him some trouble before checking for his pass signed by Arnold granting him safe passage; however, the militiamen were most concerned about the Cow Boys, a group of British marauders who made criminal mischief for residents in the area, stealing food supplies or robbing travelers. André would have been quite safe in their company, had they known his true identity—but he could not reveal himself as a British officer without tipping off Smith to the whole business. Reluctantly, André agreed that they should find shelter and resume their travels by daylight. Securing lodging at a nearby house, the men retired to rest, but, as Smith noted, “I was often disturbed with the restless motions, and uneasiness of mind exhibited by my bed-fellow, who on observing the first approach of day, summoned my servant to prepare the horses for our departure.”

  As the three men neared the bridge over the Croton River, which feeds into the Hudson River and provided the swiftest means through the remainder of the American territory back into the British-held districts approaching New York City, a profound change came over André. Shedding his anxiety and gloom, he began to be much more like the charming, cheerful wit so beloved by his comrades. “He appeared in the morning as if he had not slept an hour during the night; he at first was much dejected, but a pleasing change took place in his countenance when summoned to mount his horse,” Smith remembered.

  I observed that the nearer we approached the bridge, the more his countenance brightened into a cheerful serenity, and he became very affable; in short, I now found him highly entertaining. . . . He descanted on the richness of the scenery around us, and particularly admired, from every eminence, the grandeur of the Highland mountains, bathing their summits in the clouds from their seeming watery base at the north extremity of Haverstraw Bay. The pleasantry of converse, and mildness of the weather, so insensiably beguiled the time that we at length found ourselves at the bridge before I thought we had got half way; and I now had reason to think my fellow-traveller a very different person from the character I had at first formed of him.

  André seemed quite touched by the well-intentioned company of Smith and his servant, and as he prepared to cross over the river and leave his new friends to head home, he promised to return the saddle and bridle that he had borrowed from Smith or send payment for them, and he made an offer of “a valuable gold watch in remembrance of him
, as a keep sake, which I refused.” And with that final gesture of generosity and amiability, André directed his horse over the bridge in the direction of what he hoped would be a safe passage back to the city.

  BETRAYAL IN BOOTS

  On that same morning of September 23, three American militiamen, John Paulding, Isaac Van Wart, and David Williams, were guarding the road in a kind of no-man’s-land en route to the city. So far, the watch had been dull, with only familiar local faces passing by. But when they spotted a stranger making his way down the road, one of the members of the party whispered, “There comes a gentleman-like looking man, who appears to be well dressed, and has boots on, who you had better step out and stop if you don’t know him.”

  Paulding stepped forward and raised his firelock at the stranger. “Stand!” he demanded. “Where are you going?”

  “I am a British officer out of the country, on particular business, and I hope you won’t detain me a minute!” André said, flashing the gold watch he had previously offered to Smith either to make a play on words or else to prove his claim, as only a high-ranking gentleman could afford such a timepiece.

  “Dismount,” Paulding ordered, not amused.

  “My God, I must do anything to get ‘along,’” he said, laughing and pulling out the pass from General Benedict Arnold that granted him safe passage. Then, climbing down from the horse, he replied more seriously, “Gentlemen you had best let me go, or you will bring yourselves in trouble, for, by your stopping of me you will detain the General’s business. I’m to go to Dobb’s Ferry to meet a person there.”

  It was a difficult situation for the three men. Did they dare hold up a man with a pass from a general in order to search him? Did they dare not to?

  Finally, Paulding spoke again. “I hope you will not be offended. There are many bad people going along the road, and I do not know but perhaps you might be one. Have you any letters about you?”

  André replied coolly, “No.”

  Sensing something was amiss, the men searched his clothes but found nothing hidden. Then Paulding ordered André to remove his boots. He removed one rather reluctantly and in a slightly awkward manner. Rather than feel around in the boot itself, Paulding reached out and grasped André’s foot, where he felt paper in his stocking. “Pull off the other boot,” Paulding ordered. With three firearms pointed at his head, André had no choice but to comply. Paulding regarded the papers briefly, then announced to Van Wart and Williams, “This is a spy.”

  Williams winked at his friends. “What would you give us to let you go?”

  “Any sum of money.”

  “Would you give us your horse, saddle, bridle, watch—and a hundred guineas?”

  “Yes,” André responded. “I will direct it to any place even if it is to this very spot, so that you can get it.”

  “Would you give us more?” Williams goaded, clearly enjoying the gentleman’s distress.

  “I’ll give you any quantity of dry goods or any sum of money, and bring it to any place you might pitch upon so that you might get it.”

  “No, by God!” Paulding roared. “If you would give us ten thousand guineas, you should not stir a step.”

  The three militiamen marched their prisoner to a nearby American camp at North Castle to turn him over to Lieutenant Colonel John Jameson. Along the way, the younger two men questioned him, still not clear as to his identity but hoping to have a little fun at his expense. André’s sophisticated sensibilities finally had enough of the backwoods banter. “I beg you would ask me none till we come to some officers and then I will reveal the whole,” he pleaded. He was turned over to Jameson’s custody, and the three militiamen went on their way to resume guarding the road.

  JAMESON’S MISTAKE

  Colonel Jameson was mortified by the situation in which he now found himself. Three overeager men had just delivered to his camp a man bearing a pass from General Arnold; perhaps they were so excited at the prospect of having captured a British officer that they were blind to the fact that the pass should have automatically granted him safe passage, no questions asked—certainly arrest or detention was not necessary.

  The commandeered papers had been forwarded on for Washington’s inspection—rushed on Jameson’s special orders—but now Jameson was faced with the matter of what to do with the man currently in his custody. He certainly spoke like a rational, genteel man, not a panicked spy caught in a snare, and his simple request was to be escorted back to West Point, where General Arnold would explain everything and set the matter straight. It seemed logical to Jameson, so he hurried to make the arrangements to carry it out, lest he find himself on the receiving end of one of Arnold’s infamous angry outbursts.

  Benjamin Tallmadge, meanwhile, had just returned to North Castle that evening from a daylong scouting mission. He heard talk of the newly apprehended prisoner named John Anderson brought in that morning; something seemed strange about the story but so much had of late that it was hard to pinpoint what was so unsettling. As Tallmadge sat reviewing the letters that had accumulated in his absence, as well as those he had put aside before he left, he happened to spot a note from General Arnold sent some days previous, informing him of a certain man named John Anderson who might pass Tallmadge’s way: “I have to request that you will give him an escort of two Horse to bring him on this way to this place, and send an express to me that I may meet him.” Suddenly, it all made sense—the prisoner, the strange reports he was receiving from the Culpers in New York, and Arnold’s odd behavior.

  Tallmadge rushed to Jameson and demanded to see the prisoner, but the colonel informed him it was impossible: John Anderson was gone from North Castle on Jameson’s orders, escorted by a lieutenant with a letter explaining the situation, through the open country back to General Arnold at West Point.

  CHAPTER 14

  Another Spy at the Gallows

  Major Benjamin Tallmadge respected the chain of command and he respected his senior officers, but in this instance he knew that his commanding officer had made a perilous mistake. Colonel Jameson had sensed that something was amiss, because he had rushed the papers found on the prisoner to Washington for examination, but fear of displeasing Arnold had clouded his better judgment, prompting him to return the prisoner to Arnold as he requested. Chagrined, Jameson was willing to listen to his subordinate’s suggestions.

  Tallmadge was a spymaster and much more savvy about the backhanded operations of intelligence gathering than Jameson. Hearing a full account of the story, he recognized the seemingly disparate pieces and concluded that a major betrayal was at hand. His first thought was to suggest a daring mission designed to entrap all the involved parties. He proposed the scheme to Jameson, who found the plan much too bold. Tallmadge later wrote to a friend and historian: “[I] did not fail to state the glaring inconsistency of their conduct to Lt. Col. Jameson in a private and most friendly manner. He appeared greatly agitated, more especially when I suggested to him a plan which I wished to pursue, offering to take the entire responsibility on myself, and which, as he deemed it too perilous to permit, I will not further disclose.”

  With his first suggestion rejected, Tallmadge immediately pursued the next best way of intercepting the prisoner and returning him to their custody. Jameson remained hesitant, afraid of upsetting General Arnold, but Tallmadge finally managed to persuade him to rescind his order and bring André back to North Castle while they awaited word from Washington. Oddly enough, Jameson still insisted on informing Arnold of the turn of events. “Strange as it may seem,” Tallmadge wrote, “Lt. Col. J. would persist in his purpose of sending his letter to Gen. Arnold—The letter did go on, and was the first information that Arch Traitor received that his plot was blown up. The Officer returned [to Jameson’s camp] with his prisoner early the next morning.”

  Jameson’s decision to alert Arnold to the matter, while shocking in retrospect, was quite understandable, given Arnold’s
reputation. For one thing, Arnold was widely trusted by many officers of the Continental Army; even those who held him in contempt would generally not have anticipated that his imprudence could go so far as to commit treason. Tallmadge noted later that Jameson, in writing to Arnold about the matter, “expressed great confidence in him as I believe was the case thro’ the army. Until the papers were found on Anderson, I had no suspicion of his lack of patriotism or political integrity.” For another, Arnold was widely feared, and Jameson was willing to take extreme steps to protect himself from the man’s wrath for not following his directives. Had Tallmadge not been as acutely attuned to subtle clues and not been actively trying to piece together the Culper Ring’s reports, he, too, might have fallen under Arnold’s spell and failed to realize who John Anderson was.

  Even now, Tallmadge kept the spies in mind and realized that more than just the fate of Fort West Point was at stake. The surrender of the fort had to be stopped at all costs, but in a somewhat delicate way. André would not have broadcast his travel plans beyond a select circle, and the collapse of his plan could endanger the spies who had helped unravel the plot. If word reached the British that there was a mole in André’s inner circle, Agent 355 and any of her associates—like Townsend—could be quickly unmasked. The entire ring would collapse, and the gallows would become a little more crowded. Tallmadge would have to act swiftly but carefully.