What If…The Revolution’s Dunkirk, August 29, 1776


For all that can be said for a deterministic view of history—for the inevitability of what T. S. Elliot called “vast impersonal forces”—chance and luck (two related but altogether different phenomena) also play a part. How else to explain the events of mid-August 1776, when, badly beaten at the Battle of Long Island (Brooklyn, actually), George Washington and his small army faced what seemed to be certain annihilation by a larger British army, one of the world’s best. As David McCullough points out, nothing less than the independence of the United States was at stake. But the whims of weather were beyond prediction then, as they often still are. Perhaps in this case the most you can say about inevitability is that Washington almost always had the knack of seizing the right moment.


The day of the trial, which will in some measure decide the fate of America, is near at hand,” wrote General George Washington in mid-August 1776 from his headquarters in New York. The Declaration of Independence had been signed in Philadelphia only days before, on August 8—not July 4, as commonly believed—and for six weeks an enormous British expeditionary force, the largest ever sent to dispense with a distant foe, had been arriving in lower New York Harbor.

The first British sails had been sighted at the end of June, a great fleet looking, as one man said, like “all London afloat.” It was a spectacle such as had never been seen in American waters. And the ships had kept coming all summer. On August 13, Washington reported an “augmentation” of ninety-six ships on a single day. The day after, another twenty dropped anchor, making a total of more than 400, counting ten ships-of-the-time, twenty frigates, and several hundred transports. Fully thirty-two thousand well-equipped British and hired German troops, some of the best in the world, had landed without opposition on Staten Island—an enemy force, that is, greater than the whole population of Philadelphia, the largest city in the newly proclaimed United States of America.

The defense of New York was considered essential by Congress, largely for political reasons, but also by General Washington, who welcomed the chance for a climactic battle—a “day of trial,” as he said. Yet he had scarcely 20,000 troops and no naval force, not one fighting ship or proper transport. His was an army of volunteers, raw recruits, poorly armed, poorly supplied. The men had no tents—to cite one glaring deficiency—and few were equipped with bayonets, the weapon employed by the British with such terrifying effectiveness. As a surgeon with Washington’s army wrote, “In point of numbers, or discipline, experience in war . . . the enemy possessed the most decided advantage; beside the importance of assistance afforded by a powerful fleet.”

Among the considerable number of the men who were too sick to fight was Washington’s ablest field commander, Nathaniel Greene. Few American officers were experienced in large-scale warfare. Washington himself until now had never led an army in the field. The battle to come was to be his first as a commander.

With no way of knowing where the British might strike, Washington had chosen to split his troops, keeping half on the island of Manhattan, while the rest crossed the East River to Long Island, to dig in on the high bluffs on the river known as Brooklyn Heights—all this carried out in disregard of the old cardinal rule of never dividing an army in the face of a superior foe. When, on August 22, the British began ferrying troops across the Narrows to land further south on Long Island, about eight miles from the little village of Brooklyn, Washington responded by sending still more of his army across the East River, which, it should be noted, is not really a river at all, but a tidal strait, a mile-wide arm of the sea with especially strong currents.

“I have no doubt but a little time will produce some important events,” Washington wrote in classic understatement to the president of Congress, John Hancock.

In fact, it was a situation made for an American catastrophe. With at most 12,000 troops on Long Island, Washington faced an army of perhaps 20,000. Should there be no stopping such a force, he and his amateur soldiers would have to retreat with the river to their backs. Which is just what happened.

The furious battle of Long Island was fought several miles inland from Brooklyn Heights on Tuesday, August 27, 1776. The British, under General William Howe, outflanked, out-fought, and routed the Americans in little time. The British officers under Howe included James Grant, Henry Clinton, Lords Cornwallis and Percy, and all performed expertly. As John Adams was to conclude succinctly, “In general, our generals were outgeneralled.”

Astride a big gray horse, watching from a hillside, Washington is supposed to have said in anguish, “Good God! What brave fellows I must this day lose!” By later estimates, his losses were higher than he knew; more than 1,400 killed, wounded, or captured. Two of his generals had been taken captive. Many of his best officers were killed or missing. British use of the bayonet had been savage and on men who had surrendered as well, as one British officer proudly recorded, explaining, “You know all stratagems are lawful in war, especially against such vile enemies of the King and country.” Washington and his exhausted men fell back to the fortifications on the Heights, waiting as night fell for a final British assault, the river to the rear.

And right there and then the American cause hung in the balance. The British, as Washington seems not to have realized—or allowed himself to think—had him in a perfect trap. They had only to move a few warships into the East River and all escape would be sealed. Indeed, but for the caprices of weather, the outcome would have been altogether different.

What actually happened was extraordinary. What so obviously could have happened, and with the most far-reaching consequences, is not hard to picture.

To be sure, the individual makeup of the two commanders played a part. On the day following the battle, influenced no doubt by his experience of the year before at Bunker Hill, General Howe chose not to follow up his victory by storming the American lines on Brooklyn Heights. He saw no reason to lose any more of his army than absolutely necessary, nor any cause to hurry. William Howe almost never saw cause for hurry, but in this case with reason—he had, after all, Washington right where he wanted him.

For his part, Washington appears to have given no thought to a withdrawal, the only sensible recourse. All his instincts were to fight. On Wednesday, August 28, and again on Thursday, August 29, his food supplies nearly gone, his time clearly running out, he ordered that still more reinforcements be rowed over from New York, a decision that seems almost incomprehensible.

His men, for all their bravery and devotion to him, were worn out, hungry, and dispirited. And it had begun to rain. On August 29, the temperature dropped sharply and the rain came in torrents on the unsheltered army. During the afternoon, according to a diary kept by a local Brooklyn pastor, “Such heavy rain fell again as can hardly be remembered.” Muskets and powder were soaked. In some places men stood in flooded trenches in water up to their waists. Expecting the enemy to attack at any moment, they had to keep a constant watch. Many had not slept for days. A New York man who saw them after it was all over said he never in his life saw such wretched, exhausted-looking human beings.

Washington’s presence along the lines and his concern for the men were felt day and night. Seldom was he out of the saddle. On both August 28 and August 29, he appears to have had no rest at all.

But in their misery was their salvation. The driving rain and cold were part of a fitful, at times violent, nor’easter that had been blowing off and on for better than a week, and for all the punishment it inflicted, the wind had kept the British ships from coming upriver with the tide. For the new nation, it was an ill wind that blew great good, so long as it held.

Meantime, as the British historian Sir George Otto Trevelyan would write, “Nine thousand [or more] disheartened soldiers, the last hope of their country, were penned up, with the sea behind them and a triumphant enemy in front, shelterless and famished on a square mile of open ground swept by fierce and cold northeasterly gale . . .”

In a letter to John Hancock written at four o’clock in the morning, August 29, the crucial day, Washington reported only on the severity of the weather and the lack of tents that Congress had failed to supply, but said nothing of a retreat. He had seen five British ships attempt to come up the river and fail; and so he appears to have been banking on no change in the wind. Possibly he believed, too, that obstructions in the harbor—hulks sunk as hazards—had truly blocked the passage of all but small craft, a notion that was to prove quite wrong. In any event, having been outflanked on land, he stood perilously close to being outflanked by water.

The decision that so obviously had to be made came only later in the day, after it was learned that the British, under the cover of dark, were advancing by “regular approaches”—working through the night, throwing up entrenchments nearer and nearer the American lines—and after Washington at last accepted the likelihood of the British fleet at his back. Importantly, as he himself was to emphasize, the decision came on “the advice of my general officers.”

According to one first-hand observer, it was General Thomas Mifflin, a self-assured thirty-two-year-old “fighting Quaker” from Philadelphia, who was the most emphatic. Mifflin, who had come over from New York with the last reinforcements only the day before, had been the one who, on his night rounds, discovered that the British were digging their way forward. Immediate retreat was imperative, the only remaining choice, he told Washington. Lest anyone question his character for making such a proposal, Mifflin asked that he be put in command of the rear guard, by far the most dangerous of assignments in a retreat.

With the rain still pounding down, Washington and his generals gathered for a council of war in the Brooklyn Heights summer home of Philip Livingston, a signer of the Declaration of Independence, who was in Philadelphia attending Congress. The time was early afternoon. The purpose of the meeting, as stated in the official minutes, was “whether under all circumstances it would not be eligible to leave Long Island.” Two of the reasons given for an affirmative resolution were that the northeast wind might shift and that the consoling thought of obstructions in the harbor was now considered erroneous.

So it was decided. Preparations were set immediately in motion. An order from Washington went over to New York to collect every boat “from Hellgate on the [Long Island] Sound to Spuyten Duyvil Creek [on the Hudson] that could be kept afloat and that had either sails or oars, and have them all in the east harbor of the city by dark.”

It was said the boats were needed to transport the sick and bring still greater reinforcements over to Brooklyn. Officers on the Heights, meanwhile, were to be ready to “parade their men with their arms, accoutrements and knapsacks at 7 o’clock at the head of their encampments and there wait for orders.”

In all, it was a straightaway lie by Washington, intended to keep the truth from the men until the last moment—and thereby reduce the chance of panic—and hopefully to deceive the British—and the innumerable British spies in New York—once the roundup of boats was under way.

Most of the troops took the order to mean they were to go on the attack. A young captain of Pennsylvania volunteers, Alexander Graydon, would recall men taking time to write their wills. He, however, sensed something else was afoot. “It suddenly flashed upon my mind that a retreat was the object, and that the order . . . was but a cover to the real design.” Yet who was to say? None of the other officers who listened to his theory dared believe it. Never in years to come could he recall the long wait without thinking of the chorus in Shakespeare’s Henry V, describing the “weary and all-watched night” before Agincourt.

The first boats began crossing as soon as it turned dark. How it was all managed is almost beyond imagination. Every conceivable kind of small craft was employed, manned by Massachusetts men—soldiers from the ranks but sailors and fisherman by trade—from Marblehead and Salem, under the command of General John Glover and Colonel Israel Hutchinson. It can be said that the fate of the American army was in their hands. How readily the night could turn disastrous on the water, no less than on land, was more apparent to them than to anyone.

Everything was to be carried across—men, stores, horses, cannon. Every possible precaution had to be taken to keep silent—oars and wagon wheels were muffled with rags; orders were passed on in whispers. Every boat that pushed off, every crossing, was a race against time, and in black night and rain.

At one point, all seemed lost. Sometime near nine, the northeast wind picked up at ebb tide. The wind and current were more than sail could cope with, even in expert hands, and there were too few rowboats to carry everyone across before daylight. But in another hour or so, the wind mercifully fell off and shifted southwest, becoming the most favorable wind possible; and so the exodus resumed, all boats in service.

It went on hour after hour almost without a hitch. If ever fortune favored the brave, it was that night on the East River. Washington, who had proven considerably less than impressive in his first battle command, handled this, his first great retreat, with a steadiness and dispatch that were masterful. As untrained and inexperienced as his men may have been, however wet and miserable, they more than rose to the occasion. They stood for hours waiting their turns, then when told, moved off as silent ghosts, heading down the slopes to the river in pitch darkness, to the Brooklyn ferry landing, which was about where the Brooklyn Bridge now stands.

As the night progressed, and one regiment after another was withdrawn, the front lines grew perilously thin, to the point where there was almost no one left to stop an attack, should the enemy discover what was happening. It was the rear guard under Mifflin that had to stay to the last, keeping campfires burning and making sufficient noise to maintain the illusion of the full army in position.

The one hitch happened about two in the morning, when somehow Mifflin received orders to withdraw, only to learn on the way to the landing that it had been a dreadful mistake and that he and his men must return at once to their posts. “This was a trying business to young soldiers,” one of them later wrote. “It was nevertheless complied with.” They were back on the line before their absence was detected.

Another officer, Colonel Benjamin Tallmadge would recall, “As the dawn of the next day approached, those of us who remained in the trenches became very anxious for our own safety . . .”

Troops in substantial numbers had still to be evacuated and at the rate things were going, it appeared day would dawn before everyone was safely removed. But again “the elements” interceded, this time in the form of pea-soup fog.

It was called “a peculiar providential occurrence,” “manifestly providential,” “very favorable to the design,” “an unusual fog,” “a friendly fog,” “an American fog.” “So very dense was the atmosphere,” remembered Benjamin Tallmadge, “that I could scarcely discern a man at six yards’ distance.” And as daylight came, the fog held, covering the entire operation no less than had the night.

Tallmadge would recall that when the rear guard at last received word to pull out, and “we very joyfully bid those trenches adieu,” the fog was still “as dense as ever.”

When we reached Brooklyn ferry, the boats had not returned from their last trip, but they very soon appeared and took the whole regiment over to New York; and I think saw General Washington on the ferry stairs when I stepped into one of the last boats . . .

When the fog lifted at about seven o’clock, the British saw to their astonishment that the Americans had vanished.

Amazingly, the entire force, at least 9,000 troops, possibly more, plus baggage, provisions, horses, field guns, everything but five heavy cannon that were too deep in the mud to budge, had been transported over the river in a single night with a makeshift emergency armada assembled in a matter of hours. Not a life was lost. It is not even known that anyone was injured. And as Tallmadge remembered, Washington, risking capture, had stayed until the last boat pushed off. As it was, the only Americans captured by the British were three who stayed behind to plunder.

The “day of trial” that Washington had foreseen deciding the fate of America had turned out to be a night of trial, and one that did truly decide the fate of America as much as any battle.

It was the Dunkirk of the American Revolution—by daring amphibious rescue a beleaguered army had been saved to fight another day—and tributes to Washington would come from all quarters, from those in the ranks, from officers, delegates in Congress, and from military observers and historians then and later. A British officer of the time called the retreat “particularly glorious.” A latter-day scholar would write that, “A more skillful operation of this kind was never conducted.”

But what a very close call it had been. How readily it could have all gone wrong—had there been no northeast wind to hold the British fleet in check through the day the Battle of Long Island was fought, not to say the days immediately afterward. Or had the wind not turned southwest the night of August 29. Or had there been no fortuitous fog as a final safeguard when day broke.

What the effect would have been had British naval forces come into play off Brooklyn Heights was to be vividly demonstrated just weeks later, when, with favorable wind and tide, five warships, including the Renown with fifty guns, sailed up the East River as far as Kips Bay and from 200 yards offshore, commenced a thunderous point-blank bombardment of American defenses on Manhattan. “So terrible and so incessant a roar of guns few even in the army and navy had ever heard before,” wrote a British naval officer. Earthworks and entrenchments were destroyed in an instant, blasted to dust, while American troops fled in terror.

Had such overwhelming power been brought to bear at Brooklyn, the trap would have been closed tight. Washington and half the Continental Army would have been in the bag, captured, and the American Revolution all but finished. Without Washington there almost certainly would have been no revolution, as events were to show time and again. As the historian Trevelyan would write, “When once the wind changed and leading British frigates had . . . taken Brooklyn in the rear, the independence of the United States would have been indefinitely postponed.”

Significantly, the same circumstances as at Brooklyn were to pertain again five years later, in 1783, except that the sides were switched, when American and French armies under Washington and Rochambeau had the British trapped at Yorktown, a French fleet at their back, sealing off any possible escape and leaving the British commander, Cornwallis, and more than 7,000 men no choice but to surrender.

“Oh God! It is all over!” Lord North, the British prime minister, is said to have exclaimed on hearing the news from Yorktown. It is what might well have been heard in the halls of Congress or any number of places the summer of 1776 had there been no fateful wind and fog at Brooklyn.


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