George Washington's Secret Six

by Brian Kilmeade

  The petition went unanswered. In April 1775, combat broke out between colonists and British troops at Lexington and Concord in Massachusetts; the following month, the Second Continental Congress convened to prepare for a full-scale war. Among the delegates from Virginia was the tall, soft-spoken surveyor, farmer, and former spy widely regarded for his valor in battle and exemplary leadership in the militia during the previous war: George Washington.

  HOW TO WIN A WAR

  Following his brief stint as a spy, Washington had led thousands of troops into battle, riding tall and remaining calm through even the heaviest bombardment. Later myths grew up around Washington—that he was spoken of in native prophesies as a man favored by the gods, that no arrows could touch him. If not actually invincible, he was at least regarded as unflappable by his peers, a sober-minded man of vision, wisdom, humility, and experience. For these reasons Washington was asked to serve as the commander in chief of the Continental Army. Now, two decades after his first spying mission, he would be engaged in a battle of his own to drive from that same land the British government he had once faithfully served. Who could have imagined such an outcome? But life was a strange pageant; he understood that well enough. And Washington knew that espionage would play a more important role in this new war.

  In traditional wars that pitted monarch against monarch, there was a mutual respect for the authority of the crown even if there was a deep hatred for the person who wore it or the land claims he or she recognized. In those battles, it was all about might; the armies fought until someone was finally overpowered. Or, as had happened so often in new territories, one army fought with weapons, manpower, disease—whatever they had—until the other population was simply eradicated. Washington quickly realized that this revolution was different. King George respected no one and recognized no authority, certainly not whatever makeshift government the colonies could cobble together. His increasingly oppressive laws and his silence in the face of organized protests had made that clear. Yet the king would not seek to completely decimate the population of the colonies; dead subjects cannot pay taxes.

  No, this war would be different from any other that had come before it. Of that Washington felt sure. It would not be a fight to the death, nor could it be simply a clash of armies. If the Americans wanted to emerge victorious from this conflict, they would not try to overpower their enemy; they would simply refuse to back down or go away. They didn’t need to be conquering heroes—they just needed to survive.

  As New York slipped from his grasp, Washington saw that the Patriots would need to outmaneuver, not overpower, the enemy. And, by learning the enemy’s secrets, spies would play a crucial role in undermining British attacks through anticipating the redcoats’ next moves. It would be the only way to counter the superior numbers, training, supplies, and equipment of the British army and navy. This was especially true in the more populous cities, where the enemy had stationed large pockets of troops. There was little hope of defeating the British in head-to-head combat unless their battle plans and their weaknesses were already known.

  Unfortunately for the rough-hewn Patriot army, spying required far more accuracy and delicacy than simply aiming a cannon, and it also took more time. Unlike waging a traditional battle, wherein two armies took to a field and fired at each other for several hours or days until one side declared victory, gathering useful intelligence might take weeks or months before combat even began. Developing the sophistication and buying the time necessary to grow an effective spy ring would be difficult—especially in the locations where it mattered most.

  Recognizing the difficulty of setting up a good espionage network, Washington began converting his wartime strategy from relying on nonexistent combat strength to placing his trust in intelligence gathering even before the catastrophic loss of New York was complete. To begin, he needed one good man.

  NATHAN HALE STEPS FORWARD

  Captain Nathan Hale felt his heart leap when he learned of General Washington’s request that September. The general needed a man to venture behind enemy lines disguised as a Loyalist. He would make casual inquiries and investigations into the troop movements and supply stores and report back to Washington. His work would inform the general’s plans to take back New York City, its harbor, and the neighboring areas.

  Lieutenant Colonel Thomas Knowlton had assembled a select group of officers to inform them of the need. Each was brave, each was trustworthy, and each was silent as he stood before them asking for a volunteer. Finally, twenty-one-year-old Nathan Hale stepped forward.

  “Are you a native of Long Island?” Colonel Knowlton questioned the eager young man as they met in Knowlton’s makeshift office to discuss the particulars of the mission.

  “No, sir. Coventry, Connecticut, and from there to Yale College.”

  “Then you must have visited Long Island as a boy?”

  “No, sir. I have never been, though I do have some distant cousins there.” Hale neglected to add that those cousins were Loyalists, rightly assuming such information would give no boost to his petition.

  “Have you even a passing familiarity with the land? Perhaps from studying its geography or the surveyors’ charts?”

  “Well, sir, my good friend from college, Lieutenant Benjamin Tallmadge, often urged me to visit his family there during the summer and sometimes showed me on maps where his home was located and which were the best coves for watching the ships come in.”

  “Nothing more?”

  “No, sir.”

  The colonel shifted in his camp chair. This interview was growing uncomfortable. “How did you occupy your time at Yale?”

  “With my studies, astronomy, debates—and theatricals, sir.”

  Theatricals. Well, that was something, Knowlton thought. At least Hale would have some ability to assume a role and play it convincingly. Then again, he also knew that college plays tended to be either overwrought classical dramas of the Greeks and Romans or else hilarious farces featuring boisterous young actors more interested in laughing as their friends donned ladies’ dresses and wigs than in conveying any part of an intelligible story.

  “I see that your unit of the Connecticut militia participated in the victorious Siege of Boston last year; am I correct to assume, then, that you are a seasoned soldier acquainted with the deprivations of supplies and the stress of battle?”

  Hale blinked rapidly and color rose in his face. “No, sir. I was a schoolmaster in New London and my teaching contract did not end until that July. The siege was already over by the time I was released from my obligations. I have been involved in some small actions, but nothing of much significance. However”—he fumbled in his pocket and drew out a letter—“Lieutenant Tallmadge took it upon himself to write to me last summer when I was preparing to leave the school and join up with the Seventh Connecticut Regiment, and his words . . . well, they inspired me, sir.”

  The older man eyed Hale warily. That Tallmadge was a rising star in the Continental Army was undeniable, but Tallmadge’s own shrewdness and ability did not automatically transfer to his idealistic young friend. “What did he say that could have possibly stirred your soul so much that you would volunteer to be the lone operative in a dangerous mission?”

  “With your permission, sir?” Hale held up the letter.

  Knowlton nodded.

  “‘I am informed that you are honored by the Assembly with a Lieutenant’s commission,’” Hale began reading in a clear, strong voice that both surprised and impressed his lone audience member. Maybe the young man had been a promising thespian on the Yale stage after all. “‘I think the more extensive Service would be my choice. Our holy Religion, the honour of our God, a glorious country, & a happy constitution is what we have to defend. Some indeed may say there are others who may supply your place. True there are men who would gladly accept such a proposal but are we certain that they would be likely to answer just as good an end? . . .
We all should be ready to step forth in the common cause.’”

  The taper on the wax candle atop Knowlton’s desk sputtered a little as tiny flecks of ash fell onto the wood; otherwise, the room was silent. He weighed the conflicting thoughts in his mind. Hale certainly seemed intelligent, if wet behind the ears, and his conviction was undeniable and moving—inspiring, even. True, he knew nothing of Long Island, but a quick study on local geography and customs would be sufficient. Besides, who else had stepped up? There were no other volunteers as far as he knew, and Washington needed his man as quickly as possible. “You truly believe you can do this?”

  “I have no doubt, sir, that I am the right man.”

  “And you have no concerns about espionage being a breach of honor?”

  Hale took a deep breath, then voiced a sentiment he had clearly been mulling for some time: “I wish to be useful, and every kind of service necessary to the public good becomes honorable by being necessary. If the exigencies of my country demand a peculiar service, its claims to the performance of that service are imperious.”

  Knowlton hid a smile at the earnestness of this prepared speech but had to admire Hale’s seriousness. “How soon can you travel, Lieutenant?”

  Hale grinned. “Right away, sir.”

  “I shall inform General Washington of the fact, and of your eagerness to undertake the task at hand.” Colonel Knowlton rose to his feet, closing the interview. “Speak to no one of our meeting. You will be called upon in due time if needed. You are dismissed.”

  With a sharp salute, Hale turned on his heel and strode buoyantly out the door.

  AN ARMY OF ONE

  Washington immediately approved Hale’s assignment. On September 12, the young man was ferried across the water from Stamford, Connecticut, to Long Island. He would pose as a schoolmaster looking for work, a cover that would give him an excuse to meet leading townsmen and ask questions about the area.

  But the move was too late. As September advanced, so had the British troops, capturing the lower end of Manhattan on September 15, just three days after Hale landed. The defeat had been inevitable and Washington was prepared for the blow, but the timing could not have been worse.

  Hale had little chance to establish his identity, let alone transmit any helpful intelligence to Washington, before the attack came and changed the entire purpose of his mission. Instead of gathering clues for how the Americans might defend their last stronghold, he now had to equip them with the knowledge of how they might win back the city. Washington feared the fledgling spy would not be able to adapt.

  Not that Washington hadn’t been impressed with Hale. Quite the opposite, in fact. The passion, boldness, and just a touch of cockiness that Hale had demonstrated seemed to Washington to perfectly encapsulate the Patriot movement. But just as many questioned the wisdom of the Americans’ challenge to the British Crown, Washington, too, found himself wondering whether Hale’s fervor, while certainly admirable, was not also a little naive. Did he really know what he was getting into? Then again, did any of them? The Americans had yanked the lion’s mane, and now Hale had walked into one of its lairs.

  Washington felt keenly the responsibility for Hale’s safety, having had the final say on whether or not the mission would go forward. There was no way of knowing how the young man was coping, and this concerned Washington even more. Where was he staying? With whom was he speaking? Had he stumbled into any situations that might put him in harm’s way—more so than the mission itself, that is? Every time he heard the rapid hooves of a post-rider’s horse, he had to fight the urge to run out and seize the letters from the courier’s hands. Just as much as he craved the information Hale would be sending, Washington wanted the assurance that the young lieutenant still maintained his cover and felt confident in his ability to quietly exit Long Island when the right moment came.

  Long Island was enemy territory. Its farmland crawled with soldiers determined to hold on to their slice of land and eager to arrest anyone who might threaten their prospects of gaining more. Because the British were so firmly entrenched in their prize real estate, it was a perfect holding pen for the British army awaiting the next offensive strike, and the troops poured in. By the time Hale landed, the island was full of redcoats armed and itching for a fight with anyone who had even a whiff of Patriot sentiments about him.

  But just as potentially damning to Hale’s mission was the civilian population. While a few Patriots suffered through the occupation, the sympathies of most Long Islanders lay with King George. Even if a farmer was a Patriot, with a British military officer taking quarter in his house he was very likely to shout “God save the king!” if it kept his children safe and his fields unscathed. For this reason alone, Washington worried that a seemingly trustworthy contact might be tempted to report a suspected spy, whether out of true loyalty to the Crown or in the hopes of procuring some additional protection for his own family and property.

  Any number of innocent situations could blow Hale’s cover to a suspicious local: an ignorance of the proximity of one town to the next, the mispronunciation of a word peculiar to that region, a slip of the tongue that betrayed him as a mainlander. The flimsy nature of Hale’s cover story might easily be blown as well—what school would be looking for a teacher this far into September? Perhaps he might be spotted by an old friend and hailed with a familiarity that would be impossible to deny. A Loyalist relative might do the same thing, but with less innocent intentions. Or maybe even Hale’s own Patriotic zeal would do him in, were he unable to remain silent in the face of insults to his cause or so trusting that he shared his true feelings with someone masquerading as a sympathetic ear.

  A week passed with no disaster, and Washington breathed a sigh of relief. While the danger was still intense, he hoped Hale had established a solid cover and was out of direct suspicion. Unfortunately, his relief was premature.

  FAILURE

  On September 21, Washington spent most of the day studying maps and potential battle plans and, in the evening, writing a few letters. He had no way of knowing that at the tip of the peninsula, Nathan Hale was, at that very moment, being arrested, charged with spying, and sentenced to “be hanged by the neck until dead” the following morning.

  As if to highlight Hale’s lonely experience on Long Island, no one can say with certainty exactly where he was detected and captured, or even what activities he was engaged in before that fateful event. Somehow he made his way westward to Brooklyn, then crossed over into lower Manhattan, though no records show exactly when or how. Perhaps he only made that crossing later, as a prisoner. By some reports, he was recognized by some Loyalist cousins and reported to the British; by other reports, he mistook a British boat as the ferry sent to return him to safety; by still others, he was lulled into a false sense of security and shared the details of his plans with some Loyalist locals at a tavern and they turned him in. Whatever the case, he was captured, tried, and hanged all in the span of roughly twelve hours.

  Shortly after Hale’s body ceased to swing like a pendulum in the Park of Artillery, Captain John Montresor of His Majesty’s army set out for the American camp under a flag of truce. He was granted an audience with a young Patriot captain and aide to General Washington named Alexander Hamilton to explain the purpose of his visit and inform the Americans of the execution of Lieutenant Hale. The visit was not only a formal courtesy but also a thinly veiled warning that their sad little attempt at espionage had been an embarrassing failure.

  The news cut Washington deeply. Casualties were an unavoidable part of the ugly business of war, but had the general not known the futility of the effort even before sending Hale on his mission? Had he not immediately detected a dozen problems with the plan? Did he not sense, deep down, that it had been doomed from the start when one brave but untried young man had taken all of the responsibility upon himself? Hale’s death was a tragedy for its own sake, for the fact that Washington now had
no agent to feed him the information he desperately needed from Long Island, and because of how unnecessary it was. Had there only been a more knowledgeable, less conspicuous ring in place whose members could not only gather the necessary information but also protect one another even as they operated in anonymity, things might have gone very differently.

  Hale’s attempt to gather and convey information had been an utter failure, but he had given his beloved general something just as valuable: the recognition that Washington needed more than just one brave man on Long Island; he needed an entire network.

  A TURN AT TRENTON

  As the autumn of 1776 progressed to winter, General George Washington found himself marching from New York to New Jersey to Pennsylvania in a series of disheartening campaigns. His troops were demoralized and the civilian population even more so, as many who were formerly enthusiastic supporters of the Patriotic cause took oaths of fidelity to the king or else simply quietly withdrew their support for liberty. In October, Washington met up with reinforcements, but found their number a mere half of the five thousand troops he had anticipated. Supplies were low and he could no longer count on the local populace to show their support by selling food and other necessary supplies to the Continental Army. The British troops, on the other hand, were well supplied and their numbers bolstered by the Hessians, German mercenaries with a reputation for being boulders of men and unflappable in battle.

  Just before the celebration of Christmas, Washington was eyeing a return to New Jersey. He had to regain control of the mid-Atlantic after the disappointing autumn or lose the war, so he began to formulate a plan to attack the Hessian encampment at Trenton—a daring raid requiring yet another treacherous ferrying of men and supplies across water. Braving large masses of ice and winter winds that could easily overturn the small boats, his men would cross the river and capture the city in an attempt to break a stronghold of British control in the region.