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Hold New York, Win the War
New York, without exaggeration, is the pivot on which the entire Revolutionary War turns.
The execution of Nathan Hale on September 22, 1776, was the lowest point in a month of low points for General George Washington. First, the British had taken New York City and Long Island—the cornerstones of Washington’s strategy because of their valuable geographic and economic positions at the heart of the North American colonies. Now, Washington’s attempt at building an intelligence network to recoup that loss had failed spectacularly. Just two months after the fledgling country’s declaration of independence, there seemed to be no future for the new nation.
And yet there had been so much hope just a season ago, in spring. After successfully sending the British packing from Boston in March after a prolonged siege, Washington had begun ordering troops toward New York City, whose harbor was of tremendous tactical—and psychological—importance. If the Patriots could hold that other great port of the Northeast, victory might be within reach.
As Washington left Massachusetts on April 4, 1776, to begin his own march southward to rejoin his men, the cheerful reports sent back by the advance parties were confirmed: Farmers and tradesmen were greeting the American troops as they passed through rural villages, pressing gifts of food and drink on the soldiers who had displayed such courage and pluck fighting the redcoats.
“Enjoy this bacon,” urged local butchers, heaving slabs of salted meat onto the supply wagons.
“Fresh milk!” announced the housewives who scrambled out of their cottages wielding buckets and dippers.
Gaggles of little boys wearing homespun blue jackets gathered to parade in front of the men as they traversed through town—one child held up a twig as if playing a fife; another pretended to beat a drum in a marching rhythm; the rest chanted the popular refrain “Join or die!” as they reveled in the Patriotic fervor and holiday atmosphere.
Even the sophisticated city crowd, usually much more reserved in their displays of celebration than the country folk, had cheered in the streets as Washington crossed into Providence, Rhode Island. In roadside taverns and stylish urban coffeehouses across Connecticut, toasts were raised to the unlikely homegrown heroes and their quiet but imposing leader. As word spread up the Hudson Valley that the Continental Army was on the move, settlers who now considered themselves Americans, rather than Dutch or German or British subjects, had whispered prayers for the protection and advancement of the cause of independence.
Throughout his nine-day journey spanning four states and nearly three hundred miles of forest roads soggy with springtime mud, Washington had seen increasing hope among the people. There were dissenting voices—those whose closed shutters and drawn shades as the Continental Army passed bespoke their loyalty to King George III and the motherland. But it was clear that there was a sense of growing excitement that this wild, untested experiment in personal freedom and individual rights just might prove more powerful than the most disciplined and well-equipped fighting force on earth.
Despite the buoyant spirits of the people, Washington’s own hope was kept in check by a sober view of facts. While the Patriots had enjoyed some early victories in Massachusetts, these wins came at a high cost when compared with their tactical significance. The Battle of Bunker Hill in June 1775, however, had gone to the British, though with heavy loss of life and limb on both sides. The Siege of Boston, which ended the following March, had been a win for the Patriots, but their success was due more to the position and strength of the American fortifications than any great offensive maneuvers to rout the enemy. In the end, the British gave up on the city, leaving voluntarily rather than fleeing in an all-out retreat. General William Howe, commander in chief of the British army in North America, had his sights set on a much bigger and more agreeable prize than belligerent Boston.
New York, tenuously held by a few American troops, was desired by both sides. In the north, the Americans had secured Boston for the moment. To the south, the action had not yet reached a critical point, though its time was coming. Right now, the most pressing concern was in the middle states, where Philadelphia and New York lay vulnerable. Philadelphia was the largest city in the colonies at the time and held great symbolic status as a seat of innovation, boasting one of the first hospitals and public libraries, as well as hosting the meetings of the Continental Congress. Capturing the seat of the fledgling nation’s government would be a great victory for the British. And New York City was the linchpin—if the British won it they could bring the colonies to their knees.
As the second-most-populous city in the colonies, New York was their northern economic hub. But even more significant was New York’s location and situation—right in the center of Britain’s North American settlements and home to both a large deep-water harbor and access to the Hudson River. The army that held New York City and its waterways had a strategic advantage not only in controlling the import and export of foodstuffs and dry goods (which, in turn, affected the economic stability of the region) but also in securing a key foothold for transporting troops up and down the coast.
Maintaining control of New York would give the American fighting corps and the colonial populace a tremendous boost in confidence. Failing to capture and hold New York City and New York Harbor would certainly be an embarrassment to the British army and navy, but they would survive the blow. For the Americans, however, losing the region would be a tragedy, destroying morale, cutting off trade, and drastically lowering the odds that the Patriots would win the war.
New York’s strategic significance, from a trade perspective, was not lost on General Howe. The loss in Massachusetts was a disappointment, but Boston was not the ultimate prize for the British. Howe wanted to choke off the Revolution by isolating the northern colonies from the southern ones. If the political radicals in the somewhat geographically clustered northern cities were segregated from their counterparts in the more spread-out south, they could not cross-pollinate ideologies, and the various factions might be more easily eliminated. It was a classic case of divide and conquer, with New York City as the essential element in creating the chasm.
After regrouping in Halifax, Nova Scotia, following their defeat in Boston, the British set out for New York. On June 29, 1776, three British ships sailed into lower New York Harbor, with General Howe aboard one of them. Both sides knew a battle was imminent.
As Washington marched south in anticipation of Howe’s attack, he must have nursed the hope that the Continental Army’s muscle and moxie were enough to outfight the British and hold Manhattan. Being a seasoned fighter and a brilliant strategist, he would have understood, perhaps better than anyone else in North America at the time, that control of New York City was essential for the cause of liberty—and that keeping the city would be a daunting task.
Washington and his men arrived in New York in mid-April 1776 and settled in Manhattan. That summer news arrived that both cheered and sobered them. Fifty-six delegates had convened in the midst of stifling July heat in Philadelphia to form the Second Continental Congress, and had forged the Declaration of Independence. If ever there was a point of no return, this was it.
Knowing the attack on New York would not be long delayed, Washington made a short trip to New Jersey and Pennsylvania to meet with his generals. They discussed New York’s defenses and supplies—all while trying to anticipate the exact mode of attack. The British, meanwhile, began amassing troops on undefended Staten Island in advance of storming the American positions just across the water in Brooklyn and Manhattan.
As August dragged on, tensions mounted. A copy of the July fourth declaration had been put before the Crown, which meant that King George finally understood the seriousness of the colonists’ determination to fight. No longer would King George order his generals to show restraint in their efforts to squelch the rebels or maintain that a mere show of force would be enough to subdue the Revolution. He would not hold back. He would not show mercy. Of this Washington felt sure, and the weight of the “lives, fortunes, and sacred honor” pledged in the name of freedom rested heavily upon his shoulders.
Across the river from Washington, General Henry Clinton had arrived to help lead the attack upon the American positions in New York. As August waned, the British ships loomed large in the harbor, the growing number of redcoats on Staten Island intimidating the sparse American troops.
Faced with an impending attack, Washington sighed one August day as he surveyed the undisciplined, ragtag army at his command in lower Manhattan; his aide-de-camp shifted nervously behind him. The general cleared his throat. “General Howe is rumored to have more than thirty thousand men in the Royal Navy assembled offshore, and twenty thousand men amassed on Staten Island. And we have . . . ?”
His aide was reluctant to reply: “Ten thousand.”
If the number was a blow to Washington, he did not show it. Ever the stoic, he refused to allow this dismal news to throw him into despair. Washington was famed as a man who never lost his nerve in battle. The sound of musket fire, the crash of cannonballs, the smell of smoke—none of that seemed to shake his calm, measured way of surveying the chaos and keeping his wits about him as he led his men forward.
But despite Washington’s steely nerve, the Americans were in grave trouble. Even substantial numbers of troops meant little without proper training and equipment, and Washington’s men lacked both. Washington had the utmost confidence in his officers, but to say that the rank and file of the Continental Army was rough around the edges was an understatement. City men who had never before wielded a rifle stood with country folk who had never had a day of formal schooling. Hardy homesteaders struggled to cooperate with young men of landed wealth who had never known a moment of discomfort or hunger in their lives. Old men lined up with boys who had lied about their age to join the rebels in pursuit of adventure. They came from all over the country: from as far north as the mountains of New Hampshire and as far south as the swamps of Georgia. Many of Washington’s men had never before been more than fifty miles from the place of their birth, let alone met anyone with such a strange accent as could be found in the hills of Virginia or the Puritan settlements of Massachusetts. They were all on the side of liberty, but there the unity ended.
Most were brave, to be sure, and loyal—perhaps to a fault. And they were all passionate about their liberty. Washington knew he had the hearts of his men, but whether the passion of an undisciplined few could hold New York against the meticulously trained British forces was another question.
“Hang together or we all hang separately,” Washington mused, reciting one of the familiar mantras of the Patriot cause, as he caught a few strains of a bawdy pub song led by the Marylanders sitting around a campfire. All possible preparations against the British onslaught had been made, and he and his men would have to trust it would be enough.
Knowing that an attack was imminent, Washington had made the strategic decision to divide his men into five groups. One had already crossed the harbor to Long Island, and another was stationed in northern Manhattan to fend off a British encroachment from that direction. The other three groups were situated to defend the lower end of Manhattan. There were several land routes the British might take, but Washington felt confident that all but the least likely and somewhat untraveled route, through Jamaica Pass, were secure. And now . . . they waited.
BETRAYAL AT JAMAICA PASS
The battle was swift and devastating.
Tipped off by someone—whether a spy within Washington’s own ranks or a disgruntled Loyalist in New York was unclear—the British learned that Jamaica Pass was guarded by only five men and set out in that direction.
William Howard Jr., a young Patriot who ran a tavern with his father near Jamaica Pass, Long Island, woke about two hours after midnight on the morning of August 27 to a British soldier standing beside his bed. The soldier ordered him to get up, dress, and go downstairs. He quickly obeyed and found his father cornered by three redcoats pointing their muskets with fixed bayonets at him. A glance out the window revealed that a whole fighting unit stood at the ready upon the grounds.
General Howe waited for the two men in the barroom. Sipping a glass of commandeered liquor, he attempted, rather absurdly, to make small talk with the terrified father and son before finally getting to the point. “I must have some one of you to show me over the Rockaway Path around the pass,” he remarked, setting down his empty glass.
“We belong to the other side, General,” the father replied, “and can’t serve you against our duty.”
Howe’s reply was kind but curt. “That is all very well; stick to your country or stick to your principles when you are free to do so. But tonight, Howard, you are my prisoner, and must guide my men over the hill.”
The senior Howard began to protest, but Howe cut him off: “You have no alternative. If you refuse you will be shot.”
Shaking, and unaware of just how damaging their compliance would prove, the Howards directed General Howe safely up the winding footpath. Behind them marched ten thousand men through the vulnerable pass, arriving at the other side in time to effectively flank the Patriot general Nathan Woodhull and his men, who were occupied with the frontal assault waged against their defenses in Manhattan when daylight came. As the battle continued throughout the day, Washington recognized his miscalculation that the full contingent of British troops would storm Manhattan—the redcoats were also bringing heavy force to bear on Brooklyn. Washington shifted more men and matériel to Brooklyn, but it was too late for the Americans to recover and hold their ground. By day’s end, Brooklyn and the surrounding area was largely in British hands, with the retreating Patriots trapped in Brooklyn Heights. Manhattan alone still held, but Washington was sure it was only a matter of time until the British overtook it, too.
Washington’s troops were decimated. All told, the Americans had lost more than 300 men that day, in addition to nearly 700 wounded and 1,000 captured. The British (and their German mercenaries, the Hessians) had lost a mere 64 men, with 31 reported as missing, and 293 wounded.
A MIRACLE IN THE MIST
Things could not have gone more badly for the Continental Army, and both sides knew it. And it wasn’t over, though the cannons had ceased to fire. The fighting had taken Washington across the East River, but now he was essentially trapped in Brooklyn Heights, surrounded by the British and with no way to escape. If his troops pursued a retreat by land, they would walk directly into the British camps and be either shot on sight or captured and hanged for treason. If they took to the water to escape to Patriot-held Manhattan, they would be sitting ducks as the British fired cannonballs into the rowboats. Then again, that was likely too messy—the British prided themselves on their extreme pragmatism. No, they would probably take the more gentlemanly route of allowing their marksmen to pick off the retreating Americans one by one.
Just like that, the Revolution was all but over. Washington must have reeled at the turn of events. Maybe it was inevitable; after all, who were the colonists to think they had a chance against the mighty king of England and an empire that encircled the globe? Washington had been entrusted with the hopes, dreams, lives, and futures of every American Patriot—and he was standing on the brink of failure.
The Americans needed to get out and get out fast. If the bedraggled and punch-drunk Patriot soldiers could somehow manage to escape, they could regroup with the friendly troops waiting in American-controlled territory. It was a big “if.”
“We have no other options?” Washington asked the officers assembled with him at his makeshift headquarters in Brooklyn Heights.
There was a pause as each man looked around the table with raised eyebrows, as if asking his comrades, “Have you got any miracles to spare?”
But Washington already knew the answer. Unless he could somehow ferry nine thousand men undetected across New York Harbor, currently patrolled by the might of the Royal Navy, he would be forced to surrender or ask his men to die in a siege from which there was no foreseeable escape. And with the betrayal regarding their vulnerability at Jamaica Pass, and no individual able to convey intelligence from the British positions, there was no way to anticipate what the redcoats’ next move might be.
Washington was near despair, but he was also a man of faith. No one knows what prayers passed his lips during those tense two days as he faced almost certain defeat. As night fell on the evening of August 29, he peered over New York Harbor and knew he had no other hope. Escape by water was the only chance—and even that would take a miracle. Ordering a hasty retreat, Washington oversaw the efforts to ferry his army and their possessions—every man, beast, cannon, and rifle—safely across the water under the cover of darkness. To his relief, the British sentinels failed to spot the shadowy silhouettes of the escaping soldiers. But as the sky began to lighten, there were still men to move—and it was then that Washington’s prayers proved effective. A thick fog began to roll in, like the benevolent breath of God, providing cover and protection until every last soldier and piece of equipment reached safety on the other side. Washington’s boots were the last to leave the Brooklyn Heights side of the harbor, and the last to alight in Manhattan, which the Patriots still held.
By the time the fog had fully lifted and the British realized what had happened, the Americans were already out of the reach of British cannons. They were down, but not out—though just barely. Washington knew it would be only a matter of days before General Howe ordered an attack on the remaining American fortifications in Manhattan, which would surely fall.
Moving north to Connecticut, Washington and his men rejoiced in their escape, though the all-but-complete loss of New York was a serious blow. Gone was the optimism created by the Boston victory. Troop morale was low. Backed into a corner, Washington now realized what every small child comes to recognize when faced with the brute strength of a school-yard bully: He could not defeat his foe with manpower, arms, or any other show of force. He would have to beat the British in a battle of wits.
The Need for a Spy Ring
As if the loss of most of New York weren’t bad enough, Washington’s autumn was about to get worse. While the defeat at the Battle of Brooklyn had been a blow, the retreat had gone better than planned. Washington’s next endeavor would not be so fortunate, ending instead in disaster.
The few American troops still holding Manhattan were hanging on by a thread, and Washington was desperate to strengthen their position. To do so, he would need a spy to collect information on British plans. Espionage was not a new activity to Washington. Having fought in the French and Indian War and served as a spy himself, he understood the roots of the present conflict—an insight that would frame his use of an intelligence network in the Revolution.
THE FRENCH AND INDIAN WAR
Two decades earlier, in 1754, the British army (consisting of both soldiers from the motherland and local colonial militias) had launched a war in North America against the French army and native tribes who were attacking British citizens in regions granted in previous treaties to the British government. For the next nine years, the continent was embroiled in battles to control the various outposts and forts sprinkled across the wilderness regions of the Ohio River and Appalachian Mountains.
The previous year, Washington, just twenty-one years old, volunteered to engage with the French soldiers and learn whatever he could about their intentions and fortifications through leading conversations, as well as whatever was carelessly shared over wine bottles. As it did throughout his life, Washington’s temperate nature had served him well on that mission; he maintained his sobriety and clearheadedness so that he could report back to his superiors that the French had no intentions of quitting the country without a fight.
This conflict, in which Washington came of age, was part of the international unrest rooted in ancient rivalries and grudges resurrected by modern ambitions. But world attitudes had changed following the Treaty of Paris in 1763, and Washington’s role would change, too. France’s claims to its overseas colonies were devastated. Britain gained several of France’s North American colonies along the northern Atlantic and in the Caribbean, as well as the Florida territory held by Spain. People suddenly found themselves subject to a new crown and a new flag—sometimes even those of a former enemy. For the American colonists, who had long been subjects of the king of England (despite their Dutch, German, Irish, Scottish, Welsh, or West African ancestry) and necessarily viewed his enemies as their own, the expulsion of the French and Spanish from bordering regions lifted much of their fear of invasion and need for protection. Now they could focus more on their own interests. Recognizing that their rights and freedoms were being neither defended nor advanced by the king they had faithfully served, they began to rebel against the very government they had once relied upon for security.
ACTS OF AGGRESSION
In 1764, the British Parliament determined that the cost of the French and Indian War had been too high. Troops remained stationed in the colonies, adding to the financial strain, so additional revenues were needed to pay for their presence, as well as to tighten trade restrictions on the colonies. Over the next few years, Parliament voted to levy a series of taxes against the American colonists. The Sugar Act and the Currency Act restricted trade and the issuance of colonial money. Then Parliament expanded its reach in 1765 with the Stamp Act, which required that all printed matter—newspapers, legal contracts, pamphlets—must be produced with paper from London and embossed with a seal of verification.
This action was, in itself, not unreasonable—the colonists could be expected to help pay for their own defense. But the independent-minded colonists reacted angrily because of the act’s broader implications. All English citizens were supposed to be afforded the right of representation in Parliament, but there were no members of Parliament for the American colonies to agree to the taxation and insist that it be reasonable. The cry of “no taxation without representation” was sounded, and a Stamp Act Congress convened in New York City in October 1765 to protest the measure. The Stamp Act was eventually repealed, but others followed in its wake as King George continued to expand the power and grasp of the Crown, while simultaneously diminishing the rights of his colonial subjects.
In March 1770, the so-called Boston Massacre illustrated just how high tensions were running. British soldiers fired into a crowd of protesting Americans, killing five and wounding six. After the grassroots Sons of Liberty staged their famous Boston Tea Party in December 1773, dumping 342 chests of tea into Boston Harbor, London responded the following spring with harsh laws designed to make an example of Massachusetts as a warning to the other colonies not to challenge the Crown’s authority.
The warning was heard loud and clear, but it did not quell the fires of rebellion as Parliament had hoped. In fact, it had the opposite effect. In response to the Intolerable Acts, as the laws had been dubbed by the Americans, the First Continental Congress met in Philadelphia in September and October of 1774. Fifty-six men representing twelve of the thirteen colonies (Georgia opted not to attend) voted to unite in a series of boycotts against British goods; prominent Patriots, including Thomas Jefferson, Patrick Henry, and Henry Lee, were among the outspoken dissenters. They also resolved to send a petition of their grievances to King George in a last effort to prevent an escalation of hostilities.
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.