George Washington's Secret Six

by Brian Kilmeade

  “You’re saying I’d have license to work as I see fit—hire the men I want and carry out . . . the business the way I think it ought to go?” Woodhull asked gruffly.

  “Completely,” Tallmadge assured him. “General Washington wants the work carried out by men who know the land, the water, and the people—a local man, in other words.”

  “Who else knows about this? I don’t want my name and my business put out there to anyone I don’t know and trust.”

  “Everything would be guarded with the utmost confidence,” Tallmadge promised. “Only General Washington and I need know about your involvement.” Woodhull seemed twitchy, nervous—and not without cause. Tallmadge therefore felt there was no need to mention Brigadier General Scott, the spymaster for the Continental Army and a man with whom Tallmadge rarely saw eye-to-eye, as his hope was to bypass Scott as much as possible anyway.

  Woodhull turned the proposition over carefully in his mind. “But why me, of all the folks on Long Island you could have chosen? What are you to do if I decline your offer?”

  Tallmadge looked Woodhull in the eye. “You have a good estate with a good farm and a good income. Now, I know your sister Susannah is still living at home, but there are no wife and no children waiting at home for you whose welfare may cause you to check your daring. You know the countryside, the best places to pick up gossip, which roads to use. I’ve been away some years but you’ve stayed on at home, building a life and building relationships. I know things have been difficult since the British landed and I don’t envy what you have had to endure watching the redcoats loot and burn the places you love most. You know (God forbid!) the escape routes. But, most important, I know that no matter what mask you may wear in public right now, you believe that this war must be won for the sake of human dignity. And New York must be had if that is to happen.”

  There was a moment of silence before Woodhull spoke. “But it’s not just me. What about the others you want me to enlist? What makes you think they can be relied upon to carry out their jobs? To stay silent rather than panic the first time a lobsterback comes too near?”

  “I assume you would recruit only men you knew to be of stalwart disposition and courage commensurate to the task.”

  “So I must ask my closest friends to gamble their own fortunes and lives?”

  “We went over that already and took those concerns into account.” Tallmadge leaned forward. “Abraham, we’ve known each other for a long time. Our families have known each other for a long time. If you believe that”—he paused and checked his words—“those handful of names we’ve discussed can be trusted with a mission this important in pursuit of a cause so sacred, then so do I. I have the fullest faith in you to dispatch your duty as well as you and your assistants are able.”

  “And you promise I won’t have any dandified officers from Charleston or Boston or God knows where else landing on my sliver of land and trying to tell me about how things should work?” Woodhull insisted.

  Tallmadge raised an eyebrow. “Isn’t that exactly the sort of thing that started this war in the first place?”

  NEW IDENTITIES

  A few days later, on the afternoon of August 25, Major Tallmadge met with his commander in chief at his current encampment in White Plains, New York. The aim of this two-man congress was to allow Tallmadge to recount the meeting in Connecticut and assuage Washington’s concern on several fronts—whether Woodhull could be trusted, whether he was a skilled enough judge of character to recruit loyal men, and whether his primary aim was patriotism or profit. The other issue of utmost importance was the creation of pseudonyms. The stakes were far too high for Tallmadge and Woodhull to use their real names, especially in any kind of correspondence. In Tallmadge’s case, an intercepted letter would make him an even higher-value target should the British learn he was now dabbling in espionage. In Woodhull’s case, living in the midst of the enemy, identification meant immediate arrest likely followed by a trip to the gallows.

  The general and the major discussed the best approach to the assignment of names—at once specific enough to be clearly and instantly identifiable to the intended recipient, yet not so unusual as to obviously be a fake name nor so common that an innocent individual who happened to bear the same name might be hunted down by the enemy. Thus, Tallmadge was dubbed “John Bolton,” a mild and unassuming moniker with a surname that was among the oldest in the colonies. The genesis of Woodhull’s name was a little more creative. Charles Scott’s initials were inverted as a nod to his position as chief spymaster for the Continental Army, and Tallmadge selected “Samuel” for a first name, probably in honor of his younger brother, Samuel Tallmadge, who had done some courier work for Patriot efforts on Long Island. The last name, it has been suggested, became an adaptation of “Culpeper,” the county in Virginia that bordered the western edge of Washington’s boyhood home of Stafford County, and the region in which he did some of his early work as a surveyor. Thus, “Samuel Culper” was born.

  Pseudonyms were in place. Courier routes were set. Specifics as to the type of information Washington sought were established. The groundwork was laid for the ring to begin its work. The first two cogs, Tallmadge and Woodhull, were in place to begin turning the wheel that would steadily roll out the defeat of the British in New York. They would not disappear into their new identities and leave their old lives behind. Instead, their spy names would serve as their passports into a double life—Tallmadge as an intelligence officer with a closely guarded secret and a covert post in Connecticut where he would retrieve the latest news, and Woodhull as a man who must go unnoticed in the den while seeking ways to overthrow the lions.

  CHAPTER 5

  The Ring Springs into Action

  Woodhull had his sights set on Caleb Brewster as a fellow spy from the beginning. He had to admire the audacity of the brash longshoreman who was a bull of a man—physically huge and imposing—and was using his intimidating size and tremendous athletic skill to make himself a regular nuisance to the British. Ever the daredevil, he taunted them from his whaler laden with smuggled goods and then amazingly evaded capture. Just as Woodhull knew the landscape, Brewster knew the coves and the waterways, slipping out of reach of the British by ducking into one or another until the patrol gave up trying to catch him red-handed.

  But that had always been Brewster’s way. Back in June 1775, some local men had circulated a document declaring their determination to fight British oppression, swearing that they would never “become slaves.” Despite his usual caution, Woodhull had signed it, as had one of Benjamin Tallmadge’s brothers. So, too, had Caleb Brewster. Remembering Brewster’s signature and observing the man’s high spirits and taste for adventure, Woodhull knew that Brewster would be an easy convert to the mission.

  What Woodhull did not know was that Brewster had already embraced the thrill of espionage. The young man had been in correspondence with General Washington since July 1778—several weeks before Tallmadge had recruited Woodhull to manage the ring—reporting on the state of the British warships in New York Harbor, as well as troop movements and naval preparations around Long Island. His reports revealed little new information and were somewhat out-of-date by the time they reached Washington, but the gesture proved to the commander in chief that there were Patriots ready and willing to spy and that a well-organized ring of secret agents could yield real intelligence.

  While taking care not to be overheard, Woodhull was probably rather direct in his proposal to Brewster. The man’s vigor and fearlessness in openly defying the British navy on the Sound left little doubt about which way his sentiments lay. Already hooked on the adrenaline rush of espionage, Brewster was an easy sell. He enthusiastically agreed to ferry messages to Connecticut and even offered to add his own observations to the reports headed to Tallmadge.

  Woodhull supposed that his old friend Austin Roe, however, might prove somewhat more difficult to recruit. Roe was friends with B
rewster, and while he was jovial and spirited as well, Roe was also comfortably situated, married, firmly established in his business, and took no joy in evading arrest in a rowboat for sport. But unlike Woodhull, who could find ready buyers for his produce in the city even if he alienated his Loyalist neighbors, or Brewster, who could find work as a longshoreman at any dock that needed the hands, Roe was a tavern keeper. His livelihood was entirely dependent upon the loyal patronage of local folks and the occasional traveler who passed his way and needed a room for the night. Should the spies’ work be discovered, they could all expect something far worse than a loss of employment. But suspicions have a way of becoming whispers in small towns, and rumors about Roe’s activities could hurt his business even after the war.

  Despite initial concerns, Roe was pleased by the mission and eager to offer his service in any way he could. Now a team of three, Woodhull, Brewster, and Roe devised a plan by which their intelligence would make its way across land and water to reach General Washington. Woodhull would operate from Amos Underhill’s boardinghouse in Manhattan, a location unlikely to arouse suspicion because of Woodhull’s family connection and because he already made fairly regular visits. The information he gathered would leave the city in one of two ways. Either Roe would make the trip into the city on the pretense of purchasing provisions for his business, or else Woodhull himself would travel back to Setauket, where he would leave the papers at Roe’s tavern or a predetermined location in a field near Roe’s house so the two men would not be seen together. This “dead-drop” method was less likely to raise suspicions but presented a much higher risk of a stranger’s stumbling upon the papers before they had been picked up, so the men rarely employed it. The two families were known to be old friends—Roe’s father had purchased the building he used for his home and business from the Woodhulls back in 1759—so nothing would seem out of place even if the two men were to be seen together carrying letters for the folks at home or visiting in the city. But Roe and Woodhull took care to ensure that the patterns of their meetings would not become too predictable and seem shady to nosy locals or eagle-eyed British soldiers.

  Caleb Brewster, whose family lived just yards away from Roe, would wait for an opportunity to retrieve the papers from Roe. He would then dash across the water when the British navy had their backs turned. On the Connecticut side of the Sound, Tallmadge would be waiting for Brewster to dock and pass off the letters, which Tallmadge would then hand-deliver to the general.

  The whole process took approximately two weeks from beginning to end and offered several advantages over the more traditional method of a solitary spy slipping in to gather intelligence and then slipping back out again. Local men were less likely to raise suspicions than an outsider who suddenly appeared in the town, skulked about for a few days, and then disappeared again. Using existing routines also allowed for a longer-term observance that could note changes in patterns and procedures of the troops. And, of course, if one man attracted suspicion, the seemingly convoluted method of passing off information from one member to another would make it much more difficult for the enemy to intercept sensitive documents. The intervening step of entrusting the papers to Roe was a brilliant one. It minimized the connection between Woodhull’s frequent trips to and extended stays in the city and Brewster’s regular dashes across the water and allowed the men to avoid apparent contact. But the proximity of Brewster’s home to Roe’s made their familiarity far more natural.

  Even as the Culper Ring took shape, Tallmadge’s superior, Brigadier General Scott, still clung to the more conventional methods of dispatching spies. He had sent at least five men on separate scouting missions to Long Island, hoping to check their reports against one another for accuracy. He believed that even if one man was caught the others would not be compromised because each mission was conducted independently of the others. What Scott had failed to plan for was the capture of three of his five spies when their presence and suspicious behavior tipped off the British that all was not as it seemed.

  Washington preferred this traditional approach at first, but it soon became clear that Scott’s method cost lives, and Washington’s conscience would not allow him to keep paying that high price. Battles demanded sacrifice, but Washington could not stand to see any more spies go the way of Nathan Hale—and all for nothing. Soon after his Long Island spies were caught, Scott took a furlough and returned home to Virginia to sort out some personal business. Washington appointed Tallmadge as his replacement. At the tender age of twenty-four, Benjamin Tallmadge became the chief of intelligence, the role that would define his career and ultimately help secure the nascent country’s future.

  REPORTS BEGIN

  Almost immediately, Woodhull revealed himself to be a remarkably acute observer, as well as an extremely nervous operative. On November 23, 1778, Woodhull as Culper wrote to General Washington with a precise count of troops at various towns on Long Island, as well as a request for reimbursement for his expenses: “My business is expensive; so dangerous traveling that I am obliged to give my assistants high wages, but am as sparing as possible.”

  Washington was impressed with the detailed information he received and spoke with Tallmadge about arranging a face-to-face meeting with his brave new ringleader—a suggestion that rattled Woodhull no small amount. He thought he had made it abundantly clear to Tallmadge that he did not want his association with spying activities to be openly acknowledged in any public way. Of course, the general knew about the ring, but Woodhull felt that his personal appearance before Washington was unnecessary and would raise questions. Because he rarely traveled beyond the city, his neighbors might ask uncomfortable questions. Local friends or relatives in Washington’s camp might look askance at his presence there. Besides these objections, it is also likely that Woodhull resisted out of a sense of inferiority; later letters contain apologies for his simple and unschooled writing and his lack of a private fortune with which to bankroll the work. Even though his family held a sizable farm, they were land rich and cash poor, and Woodhull had received a practical education on growing sustainable crops rather than a classical one. Thus, a meeting with an esteemed “gentleman farmer,” an archetypal figure of both British and American mythology and of whom Washington was the ideal, would only highlight Woodhull’s own shortcomings of learning, culture, and person.

  The proposed meeting was abandoned, but Woodhull’s hackles remained raised. The more he thought about it, the more he became unnerved by the whole matter—and this agitation was not improved by a slight adjustment made to the delivery route just five weeks later, in January 1779. Instead of Tallmadge personally delivering the letters to General Washington’s hand, he was now going to pass them off to General Israel Putnam, who would then carry them and other dispatches from Danbury, Connecticut, to the commander in chief. Even though Putnam, a hero of Bunker Hill, knew nothing of the true identity of “Culper’” it was nerve-racking for Woodhull, who feared any involvement of strangers.

  Austin Roe also made a move that rankled Woodhull even further; he hired a young man named Jonas Hawkins as an occasional courier, both to dilute suspicion and to get letters into Tallmadge’s hands more quickly, because Hawkins could carry information at times when Roe’s business prevented him from traveling. Even if Hawkins was not privy to the full extent of the operation, another person now knew at least part of the secret, and this worried Woodhull. But the changes nearly halved the amount of time it took for Woodhull’s intelligence to reach Washington, from two weeks to only one. Woodhull couldn’t argue against the improvement.

  Despite his fraying nerves, Woodhull persisted with his meticulous scouting reports on Manhattan, detailing where British troops were situated and how strong their positions were. He also added a note of personal concern for the rapidly deteriorating state of affairs on Long Island. “I cannot bear the thoughts of the war continuing another year, as could wish to see an end of this great distress. Were I to undertake to give
an account of the sad destruction that the enemy makes within these lines I should fail. They have no regard to age, sex, whig or tory,” he lamented.

  Caleb Brewster supplemented the reports with his own reporting on shipbuilding activities and the particular ships in each Long Island inlet and harbor. “I have returned from the Island this day,” Brewster wrote:

  Genl. Erskine [quartermaster general of the British army] remains yet at Southampton. He has been reinforced to the number of 2500. They have three redoubts at South and East Hampton and are heaving up works at Canoe Place at a narrow pass before you get into South Hampton. They are building a number of flat bottom boats. There went a number of carpenters down last week to South Hampton. It is thought by the inhabitants that they will cross over to New London after the Continental Frigates. Col. Hewlet [of the Third Battalion, DeLancey’s brigade] remains yet on Lloyd’s Neck with 350, wood cutters included. Col. Simcoe [of the Queen’s Raiders] remains at Oyster bay with 300 Foot and Light Horse. There is no troops from Oyster Bay till you come to Jamaica. There is one Regt. of Highlanders and some at Flushing and Newtown, the numbers I cannot tell, but not a regiment at both places.

  Together, these reports began to create a rich and detailed picture of New York’s defenses, as well as provide important clues about the enemy’s future strategy.

  A SECRET WEAPON

  As the spring of 1779 crept into New York, Woodhull was near panic, obsessed with the fear that he was on the verge of being found out and arrested. He was certain that the British were suspicious of his frequent trips to Manhattan, perhaps even shadowing him to learn his whereabouts and activities in the city, and noting any patterns of behavior following his return from each trip. There was one promising development, however, which gave Woodhull a sense of relief: the long-awaited arrival of a particular concoction intended to give him an added layer of security. Washington had obtained a supply of invisible ink and issued Woodhull a vial of the precious substance for the writing of the Culper reports.