“We are in a very disaffected part of the Provence,” Washington wrote to his brothers John and Samuel in two telling and very nearly verbatim letters. Samuel’s version, dated December 18, 1776, reads:
And between you and me, I think our Affairs are in a very bad situation; not so much from the apprehension of Genl. Howe’s Army, as from the defection of New York, Jerseys, and Pennsylvania. In short, the Conduct of the Jerseys has been most Infamous. Instead of turning out to defend their Country and affording aid to our Army, they are making their submissions as fast as they can. If the Jerseys had given us any support, we might have made a stand at Hackensack and after that at Brunswick, but the few Militia that were in Arms, disbanded themselves or slunk off in such a manner upon the appearance of danger as to leave us quite unsupported and to make the best shifts we could without them and left the poor remains of our Army to make the best we could of it.
I have no doubt but that General Howe will still make an attempt upon Philadelphia this Winter. I see nothing to oppose him a fortnight hence, as the time of all the Troops, except those of Virginia (reduced almost to nothing,) and Smallwood’s Regiment of Maryland, (equally as bad) will expire in less than that time. In a word my dear Sir, if every nerve is not strain’d to recruit the New Army with all possible expedition, I think the game is pretty near up. . . .
You can form no Idea of the perplexity of my Situation. No Man, I believe, ever had a greater choice of difficulties and less means to extricate himself from them. However under a full persuasion of the justice of our Cause I cannot but think the prospect will brighten, although for a wise purpose it is, at present hid under a cloud entertain an Idea that it will finally sink tho’ it may remain for some time under a Cloud.
Washington had smiled a little, in spite of himself, as he closed the letter with greetings sent to his sister-in-law and her children. Yes, the past few months had been bleak and the future looked like it would be very much the same, but Washington clung to that shred of hope with which he had reassured his brother. Though the Patriot cause was cloaked by a cloud, his cautious optimism was rooted in something more solid than just a desperate hope that another miracle may yet come to his aid. Washington had a secret.
John Honeyman, a Scots-Irish immigrant who had served the British Crown faithfully during the French and Indian War, was now plying his trade as a weaver and butcher in Trenton, supplying the Hessian troops and making his allegiance to the Crown common knowledge. While wandering dangerously close to the American lines one day, Honeyman had been captured and questioned by none other than General Washington himself. A few days later, shortly after Washington had written to his brothers, Honeyman escaped back to Trenton under the cover of some small disturbance in the camp. Once again behind Hessian lines, he insisted upon an audience with Colonel Johann Rall, informing him of what he had observed while held by the Americans.
“There will be no attack,” Honeyman told Rall. “The American troops are so disheartened and so bedraggled, they have no plans of advancing any time soon.”
The big German laughed at the thought of the upstart colonials wasting away as they tried to put on a brave show: “Wir werden fröhliches Weihnachten schließlich haben!” (We will have a merry Christmas, after all!)
Colonel Rall dismissed the trusted tradesman with a hearty slap on the back, and went to inform his subordinates that they could stand down and commence with the Christmas celebrations. Someone had procured quite a few casks of ale, and they were all eager to toast the birth of the Christ child in roaring fashion even as the church tolled the bells marking Christmas Eve. Meanwhile, Honeyman quickly and quietly gathered his family and retreated eastward to New Brunswick, New Jersey . . . and Washington prepared to strike.
It had all been a beautifully orchestrated setup, from Honeyman’s position in Trenton to his capture, escape, and meeting with Rall. He had been a dedicated British soldier twenty years ago, but now he was Washington’s man. Learning from Hale’s death, the general had reached out to Honeyman earlier that fall, counting on his outstanding credentials from the previous war, unshakable bravery, and unsuspicious occupation to enable him to operate undetected. Sure enough, Honeyman casually questioned and carefully counted the men about the city and offered a full report of it back to Washington from his jail cell following his “capture.” Washington, having personally arranged for the means by which Honeyman could escape, had then asked his agent to plant the false story in Rall’s ear before spiriting himself and his family out of harm’s way when the attack came on the unsuspecting Hessians.
It was a perfect plan that went off without a hitch. Honeyman played his part beautifully, and the Hessian troops, all fighting massive hangovers from their raucous Christmas revelries, were caught completely off guard when the Patriots launched their attack in the wee hours of December 26. The victory was swift, decisive, and crucial for the American cause.
Washington’s espionage success further buoyed him and the troops. But the loss of Long Island and Manhattan still weighed heavily on the general’s mind. He didn’t think the war could be won without recapturing them and, like Trenton, they could not be taken without good, reliable intelligence. Honeyman’s efforts at Trenton had proved the value of a well-placed spy and taught two good lessons: Washington’s spies would have to blend in as Honeyman had (and Hale had not), and they would have to be absolutely convincing in their roles.
Washington would need a collection of agents—a ring of common men and women with unquestionable fidelity and unassuming identities. His first task would be to enlist two key individuals: (1) an officer familiar with the territory and well acquainted with the local families and customs, who could orchestrate the whole enterprise but remain close to Washington’s side, and (2) an agent on the ground who could recruit the other members, preferably a person who was well connected but had largely kept his political opinions to himself throughout the conflict thus far—a man who would not raise suspicions but would rather die than surrender his God-given liberties.
CHAPTER 3
Launching the Ring
In February 1777, Washington wrote to Nathaniel Sackett, a New York merchant, supplier to the Continental Army, and Patriot activist. The short letter got to the heart of the matter immediately. He offered Sackett fifty dollars a month—a generous sum from the cash-strapped American government—to establish a network of spies to learn “the earliest and best intelligence of the designs of the enemy.” Sackett’s efforts, while initially fruitful, collapsed a few months later in a series of unfortunate mishaps and failed missions that yielded few results of the impact Washington was seeking. Finding the right man to lead the New York ring was proving harder than planned.
In the fall of 1777, a year after Nathan Hale’s death, Washington still had no New York spy ring, mostly because the general’s attentions were diverted again from New York to Philadelphia, which the British had recently captured. For the next few months, Washington devoted most of his attention to regaining the City of Brotherly Love and placed the New York intelligence efforts on hold indefinitely.
A MISSION
As 1777 turned into 1778, the tide of the war changed. When Benjamin Franklin’s negotiations in France finally culminated in Louis XVI’s commitment to support the American cause in February 1778, the British strategy had to change. Despite a devastating winter at Valley Forge, the Americans were no longer fighting alone, scraping out victories from sheer luck, pluck, and whatever good fortune Providence threw their way. By June 1778, orders were issued for the British army in Philadelphia to abandon the city and set their sights on strengthening their all-important hold on New York.
Washington and his men prepared to follow suit, packing up the ragtag army to leave Valley Forge. The logistics of moving an army were all-consuming, but Washington was preoccupied with an even more important task—the time had come to focus his full attention on forming his spy network, and nothing w
ould distract him now.
Washington tapped Brigadier General Charles Scott, a rustic man from central Virginia, to serve as his chief of intelligence. It was a logical appointment; Scott was experienced and able, with an impressive record in command. He had distinguished himself as a scout during the French and Indian War and had served alongside Washington for the duration of the Pennsylvania campaign. But despite Scott’s capabilities and qualifications, he was abrasive and unimaginative. Even worse, his knowledge of the topography and waterways of Manhattan and Long Island was severely limited.
Quickly recognizing that Scott’s efforts could easily go the same way as Nathan Hale’s and Nathaniel Sackett’s, Washington scrambled to find another man to head up the actual infiltration of New York. He needed someone who knew not only the city and the various routes into and out of it but also enough trusted locals to recruit as spies. The candidate would also need to be nearly inexhaustible if he were to devote the time, strategy, and energy necessary to make the ring successful.
Fortunately for Washington, one of the rising young stars of the Continental Army fit the bill exactly. Benjamin Tallmadge, a gallant young major whose curls always seemed to be escaping beneath his sharp dragoon helmet, was still rather green, but his keenness of mind was apparent to everyone who met him, and he knew how to earn the respect and faith of his men despite the occasional misstep. Besides, his demonstrated courage, his imagination, and, most important, his background made him the perfect candidate.
A RISING STAR
Major Benjamin Tallmadge was a rather unlikely military man. He was born on February 25, 1754, the second son of the Reverend Benjamin and Susannah Smith Tallmadge, in a parsonage in Setauket, a hamlet in the region of Brookhaven, Suffolk County, Long Island. The son and grandson of a minister, young Benjamin seemed destined for the pulpit rather than the trenches.
Benjamin Junior was an extremely bright, precocious child. One of his father’s duties as parson was to instruct the young men of the village who were hoping to attend college, preparing them for the rigorous entrance exams by supplying them with the requisite knowledge of Latin, Greek, theology, and rhetoric. Energetic and enthusiastic about anything that seemed remotely challenging, young Benjamin was eager to join his father’s classes and thrived under increasingly difficult curricula. By the age of twelve or thirteen, he had proved so proficient that he was admitted to Yale by the college president, but the Reverend Tallmadge felt his son was too young. At his father’s bidding, Benjamin waited until he was fifteen to enroll. In the meantime, Susannah died, leaving the Tallmadge men alone in the parsonage. The sadness in the house following her passing was oppressive, and Benjamin found that leaving was something of a relief.
He was well prepared for college life. “Being so well versed in the Latin and Greek languages, I had not much occasion to study during the first two years of my collegiate life,” Tallmadge later admitted, “which I have always thought had a tendency to make me idle.” But his time was not wasted. He quickly became popular among his classmates, including Nathan Hale, who found Tallmadge’s intelligence, energy, and good nature fascinating.
Playhouses were very rare in the colonies at the time, and public opinion considered theater somewhere between frivolous and downright sinful. This irresistible combination of novelty and potential scandal made theatricals a favorite pastime among college students. Tallmadge and Hale were often at the center of these productions, and frequented several other clubs that explored the various disciplines future schoolmasters should master: astronomy, geometry, history, debate, and natural sciences. These subjects were also covered in classes, but this was the Age of Enlightenment and the pursuit of knowledge was all the rage—even among fun-loving young men.
Benjamin graduated from Yale in 1773 with a distinguished academic record, despite his somewhat lackadaisical freshman and sophomore years, and a severe bout of measles that marked part of his junior and senior years; he was even invited by the college president to speak at the commencement ceremony. Upon graduation, the position of superintendent of the high school in Wethersfield, Connecticut, was offered to him, and Tallmadge seized the opportunity to impart his enthusiasm for study to a younger generation. There, he served faithfully for three years, though his ambitions drew him toward the legal profession and he began to seriously consider studying law.
But in the spring of 1775, “the shot heard ’round the world” rang out at Lexington, Massachusetts, followed by a skirmish at Concord a few hours later. That one day, April 19, would mark an indelible change in the course of history, and Benjamin Tallmadge, like many other young men of his time, was swept up in Patriotic fervor as the War of Independence officially began. The bloody battle at Bunker Hill raged shortly afterward in June, and Tallmadge took advantage of his school’s summer holiday to ride the one hundred miles to Boston to learn of the latest news firsthand. He met with some Connecticut friends who had been involved in the combat, and their stories of heroism and zeal began to shift Tallmadge’s goal from fighting injustice in the courtroom to fighting tyranny on the battlefield.
He began the fall term at Wethersfield seriously weighing various courses for his future. With the arrival of 1776, the Continental Congress gave approval for the colonies to actively expand their fighting brigades. Captain John Chester, one of friends with whom Tallmadge had visited the previous summer, was elevated to the rank of colonel, and invited Tallmadge to join his regiment as a commissioned officer. Thus, Lieutenant Benjamin Tallmadge, his commission signed by Governor Jonathan Trumbull, took his leave of the school at the end of the term and officially became a member of Connecticut’s Continental Line on June 20, 1776.
It was a move that astonished Benjamin’s father and his second wife, the former Miss Zipporah Strong. As his unit marched toward Manhattan, Lieutenant Tallmadge gained leave to venture across the water to Long Island to see his family. His pious father was shocked to learn that both Benjamin and his older son, William, had enlisted, but he granted his blessing at Benjamin’s request.
Now a soldier, Tallmadge continued to distinguish himself with his boundless energy and uncanny knack for winning people over, but the art of war didn’t come easily to the new recruit. With August came the fateful Battle of Brooklyn and the betrayal of Brigadier General Nathaniel Woodhull and his branch of the Long Island militia at Jamaica Pass. The battle was Tallmadge’s first taste of war, and it shook him.
“This was the first time in my life that I had witnessed the awful scene of a battle, when man was engaged to destroy his fellow-man,” Tallmadge wrote more than fifty years later. “I well remember my sensations on the occasion, for they were solemn beyond description, and very hardly could I bring my mind to be willing to attempt the life of a fellow-creature.”
Their father’s blessing proved fruitful for Benjamin but not for his brother William. At the same time that Benjamin was experiencing such a conflict of conscience at the horror of killing, William was being hauled off as a prisoner, captured in battle by the British. In the desperate weeks that followed, Benjamin’s good nature and dogged determination failed him for perhaps the first time in his life. Together with some influential friends, he made repeated attempts to have provisions delivered to William in the British prison ship where he was being held, but all efforts were rebuffed, all food parcels and blankets denied. William starved to death at some point in the autumn of 1776, and his body was either thrown over the side of the ship into cold New York Harbor or buried in an unmarked grave on the shore.
Nathan Hale’s death, coinciding with William’s desperate plight, was a difficult blow. Tallmadge’s conscience shouted that he would have been a far better man for the job than poor Hale, who had never even set foot on Long Island. But the opportunity had not been offered to Tallmadge and he had precious little time to dwell on the tragedy. His unit continued to march with General Washington, engaging in the Battle of White Plains on October 28, when Be
njamin himself was very nearly captured by Hessian troops as he was ushering his men across the river.
In mid-December 1776, Benjamin Tallmadge was appointed captain of the Second Continental Light Dragoons by General George Washington himself, who had admired the young man’s abilities and conduct, not to mention his loyalty. The appointment was signed in the unmistakable hand of John Hancock, and Tallmadge accepted it willingly. He devoted the first third of 1777 to training men and horses for reconnaissance, scouting missions, and light raids ahead of the more heavily armed cavalry and artillery brigades, a job, Tallmadge later wrote, that he enjoyed thoroughly: “My own troop was composed entirely of dapple gray horses, which, with black straps and black bear-skin holster-covers, looked superb. I have no hesitation in acknowledging that I was very proud of this command.”
Tallmadge continued his dedicated and distinguished service, and a promotion to major followed in April 1777. At the end of that year, something happened that would change his career. After an attack on his troops, Tallmadge received word of an unusual nature. As he described it, “a country girl had gone into Philadelphia; with eggs, instructed to obtain some information respecting the enemy.” Arrangements were made that she should meet Tallmadge at the Rising Sun Tavern, where she quickly passed on all information about troop numbers and supply counts that she had been able to gather, likely from another sympathetic contact inside the city.
But the Rising Sun was not an ideal place for cover, as it was clearly visible from the British lines, and Tallmadge was spotted and identified entering the establishment. While the girl was still offering her report, the alarm was sounded that an armed British guard was fast approaching; Tallmadge dashed outside, swung the girl up behind him on his horse, and the two took off at full speed, streaking toward Germantown, a little more than three miles away, with the British in close pursuit. Once in the safety of town, the girl dismounted and disappeared, and Tallmadge began to make his way back to his unit.
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