George Washington's Secret Six

by Brian Kilmeade

  But the experience of the young citizen-spy stayed with him. “During the whole ride,” he recorded in his memoirs, “although there was considerable firing of pistols, and not a little wheeling and charging, she remained unmoved, and never once complained for fear after she mounted my horse. I was delighted with this transaction, and received many compliments from those who became acquainted with it.”

  Bravery and resolve from the most unlikely corners could still be counted on to rise to the challenge and take on whatever mission was necessary for the sake of freedom. The safety of those souls was also a sacred trust. That much was clear to Tallmadge, and soon he would not only have another chance to see such courage in action but also be a willing player.

  During that brutal winter of 1777 and into January 1778, Tallmadge stayed close to General Washington at Valley Forge; in such cramped and miserable quarters, the young officer impressed his commander. He was still somewhat untested and not always as farsighted as more seasoned officers, but it was clear that both his input and his unsinkable enthusiasm were valued by both subordinates and superiors.

  When Washington tapped him to act as spymaster on Long Island, Tallmadge acted quickly. He knew right away whom he would approach to be his man on the ground.

  CHAPTER 4

  Crossing the Sound

  Growing up, Abraham Woodhull had been a neighbor of Tallmadge’s, and he shared many of the young officer’s ideals, but that’s where their resemblance ended. By all accounts, Woodhull was no bright-eyed, optimistic, jolly-young-man-turned-soldier who ran eagerly into the welcoming arms of the American cause. His sentiments lay with liberty, but as a confirmed bachelor and self-proclaimed old man before the age of thirty, he put such a premium on personal autonomy that he avoided official military service, where he would have been subject to the orders of superiors.

  Abraham was his parents’ third son, raised under the shadow of a prominent and celebrated family (which included the ill-fated General Nathan Woodhull, a cousin) to be neither the heir nor the spare to the paternal estate. While his older brothers, Richard V and Adam, were groomed to step into the role of American gentlemen, young Abraham was released to the freedom of the outdoors. It was a dismissal he neither minded nor resented, as he found the tedium of schoolwork uninspiring. While his brothers were laboring over passages of classical rhetoric, Abraham gained an intimate knowledge of the landscape of Long Island, connecting every topographical feature with its owner.

  The Woodhull girls, Susannah and Mary, doted on their baby brother, and Abraham was equally fond of them. When Mary married Amos Underhill and moved with him to Manhattan, Abraham made a habit of visiting them. Sometimes he traversed Long Island and then crossed the East River to Manhattan, and other times he caught a ride with a longshoreman rowing across Long Island Sound to Connecticut and then traveled southward to the city. He enjoyed these trips, but the family was soon to face difficult times. In 1768, at the age of twenty-one, Adam died; six years later, at the age of thirty, Richard V died. And so, in 1774, Abraham found himself suddenly and unexpectedly in position to inherit the Woodhull family’s homestead.

  It was a windfall he had neither hoped for when it was out of reach nor relished now that it was his. He had never considered himself cut from the same fabric as the rest of the prominent landowners, and had gone to some pains to distinguish himself from their upright and uptight behavior. Abraham Woodhull was proud of being the black sheep of his straitlaced family, and he assumed the burden of familial duty with reluctance; it smacked of Old World thinking. If he was to reject King George’s authority on the basis that the monarch had simply been born into his position, why could he not also reject his own family’s expectations for him to pick up the mantle of Woodhull respectability simply because he was the sole surviving son-of-a-son-of-a-son-of-a-son-of-a-son?

  OCCUPIED NEW YORK

  When war erupted the following year, Woodhull’s journeys to Manhattan by both the northern and the southern routes became more perilous, though he continued to visit his sister whenever he could. By 1777, New York had fallen from quite a height of Patriotic fervor. Manhattan and its surrounding areas had always leaned Loyalist, but in the early years of the conflict, there was still a significant Patriot population. When the newly penned Declaration of Independence was read publicly the summer before, the reaction had been wildly enthusiastic. Rowdy Patriots tore down a statue of King George in spontaneous protest and melted its four thousand pounds of lead for bullets. General George Washington, while appreciating the mettle (and resourcefulness) demonstrated, chastised some of his own officers involved in what he viewed as an undignified and disrespectful act.

  After the British proved victorious at the Battle of Brooklyn and then with the fall of Manhattan, in August and September of 1776, respectively, there was a demographic shift as many Patriots left the city for more like-minded locales and Loyalists flooded into the city that was viewed as a safe haven for those who sided with the Crown. The fire that raged through a significant portion of the city following the Americans’ retreat also contributed to the change in population. More than one Patriot lost his home or business to the fire. It might have been worth staying and rebuilding had the conquering army been a sympathetic one, but the loss of shelter, livelihood, and political power was too much for many people to bear all at once.

  What destruction and politics didn’t drive out, filth did. Nicholas Cresswell, an Englishman visiting New York, recorded his disgust with the state of the city following the winter thaw in the spring of 1777. He complained about the sheer number of people crowded into the city’s confines, “almost like herrings in a barrel, most of them very dirty and not a small number sick of some disease, the Itch, Pox, Fever, or Flux.” He further opined, “If any author had an inclination to write a treatise upon stinks and ill smells, he never could meet with more subject matter than in New York.”

  For those well-to-do Loyalists who stayed in the city because it was their home, the general squalor was of little concern; there was still a sparkling social scene full of dinner parties and balls, providing a glittering mask of denial. After all, such was urban life, and New York was certainly large enough to absorb whatever elements came its way. The British officers stationed there enjoyed the high life, only occasionally interrupted by the necessary evil of having to earn their pay by leading troops into battle. When the tents were struck and the cannon smoke cleared, they went back to living it up in the ballrooms, coffeehouses, and taverns of Manhattan.

  The common foot soldiers stationed there were hardly enjoying the same privileges as their commissioned leadership, but they, too, had the benefits of steady pay and the automatic authority conferred by their uniforms. Life for civilians who were less well-off was harder, as they competed for what resources were left over after the troops were supplied.

  For those Patriots who remained behind when the American troops withdrew, life became a kind of fragile maze; it could be successfully navigated if one trod carefully, but a wrong turn or false move could leave one isolated and alone, and a single errant step could cause an irreparable crack. The physical fighting between armies had subsided, but that did not mean peace had filled the vacuum.

  Yet despite the disease, stink, vice, and every other undesirable trait with which the city was plagued, New York was still the most desirable piece of real estate on the North American continent. As the geographical heart of the English eastern seaboard, it was strategically significant from both a naval and an economic perspective. And it was still solidly outside of General Washington’s grasp—but not out of reach of Abraham Woodhull. Whether or not he was transporting goods back and forth between Manhattan and Long Island without official British sanction was, by his own estimation, no one’s business but his own. After all, it was his neck on the line if he was caught.

  SMUGGLING

  Woodhull was infinitely practical and took pride in his pragmatism. What
use did a farmer have for frivolity? Unlike a merchant, whose profitability hinged on the art of accurately reading and predicting the social whims of the spending public, a farmer depended on the hard science of nature for his livelihood. But sometimes those worlds intersected—a farmer with a shrewd business sense could capitalize on the tastes and trends of the general population by trading his produce for luxury goods that he could sell for a hefty profit while never having to indulge in the trappings of fashionability himself. What could be more practical than that?

  Urbane, bustling New York imported exotic and high-end merchandise from around the globe; such trade was the basis of much of its economy. But its cobblestone streets and tightly packed homes and businesses left little earth for gardens, let alone large-scale farming. And yet the population needed to eat. North of the city, working farms dotted the Hudson Valley, but those areas were largely in Patriot hands. British soldiers closely monitored every road in and out of Manhattan, and farmers who brought in wagons of meats, grains, cheeses, and vegetables for sale in the city were likely to face taxes or even confiscation of part of their goods. Still, it was good business, even if some losses had to be factored in as part of the game.

  The farmers and fishermen on Long Island devised ways to get around the British taxes. Some took the ferry that ran between Brooklyn and Manhattan, carrying bundles of food disguised as ordinary goods of little interest to the authorities; others found their own means of transport. One or two men could cross the Sound due west to largely Patriot Connecticut, then travel by foot or else row south to Manhattan with a well-stocked whaleboat. After quickly and easily unloading their goods at high prices to city residents hungry for fresh, wholesome produce, they would fill the skiff up with tea, spices, foreign wines, and trinkets not available on Long Island that they could buy cheaply in the city. Some of these capitalists traded for their own gratification (or that of their families); others, like Woodhull, found they could sell the goods at exaggerated prices to the isolated and luxury-starved residents of Long Island. It was a simple case of supply and demand. Luxury goods were wanted and Woodhull was happy to supply them—in return for silver.

  But it was also risky business. The Sound was patrolled by the formidable British navy and, even though smuggling was accepted as common practice, an example was sometimes made of violators. Men who were caught could face anything from a stern warning to a heavy fine to imprisonment. Those who were not caught could expect to live rather comfortably.

  Woodhull found himself favoring the lower-risk route of the Brooklyn ferry as he once again began making his regular trips from his home in Setauket to visit his sister Mary and her husband, Amos Underhill, at their Manhattan boardinghouse. This family connection gave him a warm meal and a roof over his head for the night, possibly a built-in clientele (if not among boarders then among neighbors) for his smuggled goods, and, most important, a plausible reason to be headed for the city with regularity. New York was not in a state of siege, and private citizens could travel with some degree of freedom, but regulations were certainly tightened and the occupying army was always on the lookout for suspicious activity that might belie smuggling or even espionage. Of the former, Woodhull was certainly guilty; he had little thought of the latter yet.

  Woodhull held his political cards close to the vest; he knew what happened to the families of outspoken dissenters. Even if he chafed under a sense of inherited obligation, he still felt the weight of responsibility to care for his aging parents and his sister Susannah. He quickly squelched any burgeoning sense of Patriotic duty that tried to take root in his mind or in his heart. He couldn’t leave to join the army, even if his personality had been better suited for military service. Not with both of his brothers now dead.

  No, his place was in Setauket, even if it meant having to endure the inconvenience of the redcoats’ watchful eyes on all trade and commerce.

  ISLAND LIFE

  While New Yorkers were facing their own uncertain future, their friends and relations across the Sound were finding their lives even more disrupted. The soaring population, crime, and demand on resources may not have been anything new to Manhattan residents, but for Long Islanders, it was quite a change from their idyllic existence prior to the war.

  In the second half of the eighteenth century, Long Island was still largely rural and wooded, with the town green in front of the church often the only open area for acres in any direction, save for a few cleared patches for crops and pasturelands. Even the shorelines were dense with trees. Combined with the rugged topography of the land itself, that meant sweeping vistas of the sea were not nearly as common as boggy inlets that overlooked more forests or were situated at the foot of small, hilly farms. Fresh produce, meats, cheese, milk, and eggs from these small estates all fetched high prices in the city, though the trade was tightly regulated by the British.

  The farmers were supposed to be fairly compensated for whatever goods were procured for the occupying soldiers, but this was not always the case. Instead of cash, locals were often given promissory notes that later proved worthless; sometimes boisterous troops simply helped themselves to a farmer’s livestock or orchard, or to a tavern keeper’s ale. Even more concerning was the wanton disregard for land rights. The British disassembled fences and barns for the sake of lumber, which cost the owner time and money for repair and replacement and also threatened the future viability of the farm by allowing animals to get loose or exposing plowing equipment to the elements. If the landowner objected to being so grossly misused by the British, he was told to take his complaints to the officer in charge. Disciplinary measures and restitution were never guaranteed—consequences varied according to the moral character of the presiding officer.

  All around the British-occupied areas of New York and New Jersey, reports of attacks upon local women by both individual soldiers and groups of the garrisoned troops were made with startling regularity as early as the summer of 1776. Many cases were handled with a casual nonchalance as simply part of the collateral damage of war. On August 5, 1776, Lord Rawdon, a cavalry officer stationed on Staten Island, wrote a rather cavalier letter to his good friend Francis Hastings, tenth Earl of Huntingdon, back home in England, in which Rawdon declared:

  The fair nymphs of this isle are in wonderful tribulation, as the fresh meat our men have got here has made them as riotous as satyrs. A girl cannot step into the bushes to pluck a rose without running the most imminent risk of being ravished, and they are so little accustomed to these vigorous methods that they don’t bear them with the proper resignation, and of consequence we have most entertaining courts-martial every day.

  In the city, there was already a growing industry catering to the carnal urges of the occupying troops. As Woodhull’s sister Mary surely discovered, running a reputable boardinghouse in Manhattan was a growing challenge as the demand grew for rooms that offered more than just a cot, a basin for washing, and a hot meal. But on the more provincial Staten Island and on Long Island there were not nearly as many opportunities for paid pleasure—so women found themselves afraid for their safety even as upper- and middle-class families were often required to open their houses for quartering soldiers. With many men away fighting on either side, or being held as political prisoners, wives and daughters left behind to tend to a house full of strange men with muskets found themselves in a precarious situation. Even if most officers conducted themselves as befitted an English gentleman, there was a nervous tension, a constant fear and distrust that settled over each town where the king’s men made themselves at home.

  Woodhull had noticed it in the eyes of the men and women he passed on the street each day—that fear and weariness of a war that was still relatively young. Many islanders expressed little or no opinion as they went about their daily lives, but there were some who seemed to speak to one another through glances:

  “Did we not welcome the king’s army like loyal subjects? Is this how we are to be repaid?�
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  “Must we go without so they can live in abundance?”

  “They attack our farms and our daughters, and yet we are forced to keep silent or be branded a traitor.”

  “I am subject to King George with my land, my money, and my fidelity but—by God!—I am not subject to his men and certainly not under my own roof!”

  AN INTERVIEW

  How exactly Tallmadge and Woodhull reconnected and concocted the first phase of their plan is not exactly clear. It is almost certain that Tallmadge intercepted his old neighbor and family friend in Connecticut, as the risk of setting foot in occupied New York City or Long Island would have been too great. Most of Connecticut was still solidly in American hands in August 1778, providing a good meeting point for the two men.

  Under heavy cover, whether at a local watering hole or within the home of a well-vetted government official with proven allegiances, Tallmadge informed Woodhull of his charge from Washington. He was to install a ring of spies to convey information from Manhattan either directly over the border to Connecticut or, perhaps more safely, across the Sound to Long Island and from there to the more rural areas of Connecticut—and thus much farther from British inspectors who might possibly intercept the intelligence. There, Tallmadge could receive and analyze the sensitive information before spiriting it away to wherever Washington happened to be encamped at the time, which was almost always within just a few days’ ride of New York City.