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George Washington: Defeated at the Battle of Long Island

Originally published by American History magazine. Published Online: June 12, 2006 
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General George Washington knew he had badly miscalculated. On August 27, 1776, British forces under a far more experienced military professional, General Sir William Howe, had soundly drubbed the American army in the Battle of Long Island and were now poised to finish it off. Outnumbered and out- generaled, with their backs to the East River and the British in front of them, the Americans appeared doomed. If Washington lost his army, it could mean the end of the Revolution.

Washington was well aware that his experience in the French and Indian War, 20 years earlier, hardly qualified him for his current position as commander in chief of the American armies. As a young colonial officer serving the British, Washington had lost a battle to the French at his hastily erected Fort Necessity in 1754. Serving as a militia colonel under British General Edward Braddock in 1755, the Virginian had fought gallantly at Fort Duquesne, but the British lost anyway. His one success had been a surprise attack against a small French party early in the war. 'I heard the bullets whistle,' Washington wrote to his brother Lawrence afterward; 'and believe me, there is something charming in the sound.' (After a London newspaper printed Washington's letter, King George II wryly remarked, 'He would not say so had he heard many.') The Americans were finding the sound somewhat less charming after the battles at Lexington, Concord, and Bunker Hill. Whether they were prepared for it or not, the colonies were now at war — a war requiring an army and a commander in chief to lead it.

Patriot leader John Adams and his cousin Samuel knew that finding a commander acceptable to all the colonies would be difficult. Charles Lee, Benjamin Church, Israel Putnam, and even John Hancock wanted the position. But the two Adams men decided Washington would lend dignity to the cause. Furthermore, placing a Virginian in the post would help deflect criticism that Massachusetts was dominating the Revolution. Although he did not lobby for the post, Washington signaled his willingness to accept it by wearing his scarlet and blue uniform of the Virginia militia to the meetings of the Second Continental Congress.

On June 15, 1775, the Congress approved the choice of Washington. The new commander in chief then read a letter of acceptance. 'Mr. President, tho' I am truly sensible of the high honour done me in this appointment, yet I feel distress from the consciousness that my abilities and Military experience may not be equal to the extensive and important Trust,' he said. 'However, as the Congress desires, I will enter upon the momentous duty and, exert every power I Possess in their service for the Support of the Glorious Cause . . . .' He also said he would keep an 'exact account' of his expenses and that he would accept no more than that for his service.

Washington achieved a quick victory in Boston when he placed cannon captured at Fort Ticonderoga atop Dorchester Heights and forced the British out of the city. Washington and his most experienced and trusted commander at that time, General Charles Lee, believed that the British would probably focus their efforts on the New York area. It was a logical assumption. If General Howe controlled New York City, he could send armies north or south while his brother, Admiral Richard 'Black Dick' Howe, could easily lend naval support wherever General Howe might need it.

Washington and Lee knew it would be difficult to defend New York, but it was a political necessity. At the very least the Americans had to make the British pay severely for the city, as they had made them pay at Bunker Hill. So with Lee back in the Boston area, Washington marched to New York to try to accomplish the nearly impossible. He planned to defend New York City by digging in and making earthworks for gun positions in Manhattan, in Brooklyn, and on the Battery. In addition, he intended to build Fort Washington up on Manhattan Island's northern tip. The fortifications themselves were well engineered and executed, but the plan was too ambitious and spread the Patriot forces too thin.

General Washington placed his largest contingent of troops, numbering 4,000 and commanded by Nathanael Greene, on Long Island's Brooklyn Heights, overlooking Brooklyn and New York City. He considered these soldiers to be his best units. On paper Washington probably had about 20,000 men in his army. But half of them were in various state militias, poorly trained, poorly equipped, and lacking discipline. Many in the regular army suffered from camp diseases and were too ill to fight. Facing them were General Howe and approximately 32,000 soldiers, including some 8,000 Hessians. Admiral Howe supported his brother with the largest expeditionary force Britain had ever dispatched — 10,000 sailors on 30 warships, with 1,200 guns and hundreds of supporting vessels. 'Every thing breathes the Appearance of War,' wrote the commander of one British frigate. 'The Number of Transports are incredible. I believe there are more than 500 of different kinds, besides the King's ships — a Force so formidable would make the first Power in Europe tremble . . . .'

On August 22 the British made their opening moves. In six hours Admiral Howe efficiently ferried his brother's troops from Staten Island to Long Island and landed them below Greene's position on Brooklyn Heights. Unfortunately for the Americans, Greene had become seriously ill, and Washington replaced him with John Sullivan of New Hampshire. Dissatisfied with Sullivan's performance, Washington put another New Englander, Israel Putnam of Connecticut, in his place. As a result, he had a commander in the field who had no knowledge of the local terrain.

Washington worried about how his largely untested army would stand up under fire. In an attempt to motivate his men, he wrote out general orders and had them read to his troops. 'The time is now near at hand, which must probably determine whether Americans are to be freemen or slaves; whether they are to have any property they can call their own; whether their homes and farms are to be pillaged and destroyed. The fate of unborn millions will now depend, under God, on the conduct and courage of this army . . . . We have therefore to resolve to conquer or die… ' General Putnam set up his line of defense on a wooded rise called the Heights of Guan. The ridge ran roughly parallel to the East River behind it. Four passes cut through the heights. The Americans were defending three of them, but in a colossal strategic blunder Putnam left the one on his left flank, Jamaica Pass, unprotected. It was all the advantage Howe needed. On the night of August 26 the British general personally took charge of a force of 10,000 troops under Sir Henry Clinton, Lord Charles Cornwallis, and Sir Hugh Percy and, guided by local Tories, moved through Jamaica Pass so he could fall upon the Americans from the rear. Early the next morning cannons signaled the British to begin their attack all along the American front. General Philip von Heister's Hessians kept the American center busy, while General James Grant's 5,000 troops hit the American right. Then Howe's 10,000 soldiers emerged from Jamaica Pass and wrapped up the unprotected left flank and the American rear. Howe's surprise was complete. '[W]e were ordered to attempt a retreat by fighting our way through the enemy, who had . . . nearly filled every field and road between us and our lines [at Brooklyn],' wrote an American soldier. 'We had not retreated a quarter of a mile before we were fired upon by an advanced part of the enemy, and those upon our rear were playing upon us with their artillery. Our men fought with more than Roman virtue . . . .' The Hessians moving in from the center attacked especially fiercely — sometimes bayoneting Americans trying to surrender. 'We took care to tell the Hessians that the Rebels had resolved to give no quarters to them in particular, which made them fight desperately and put all to death that fell into their hands,' a British soldier wrote.

The day proved to be a disaster for the Americans, but it would have been even worse if not for the action of William Smallwood's regiment of 400 to 500 men from Maryland, temporarily commanded by a young and capable major named Mordecai Gist. Although inexperienced, they were among the best and bravest troops that day. While under fierce attack they made an orderly retreat to the Cortelyou house, a stone structure that commanded the Mill Dam Road and bridge, the only escape route across the Gowanus Salt Marsh.

American General William Alexander (who claimed a Scottish title and called himself Lord Stirling) ordered Gist and 250 men to hold off the enemy while the other Americans withdrew across the Mill Dam Road. Not only did Gist's men hold off the British, they made six counterattacks before being forced to scatter and make their individual ways back to the American lines. Watching from afar, General Washington turned to Israel Putnam. 'Good God, what brave fellows I must this day lose,' he said. Those few surviving Marylanders who could swim and who were lucky made it back. 'There was in this action a regiment of Maryland troops (volunteers), all young gentlemen,' recalled Joseph Plumb Martin, then 17 years old and a member of the nearby Connecticut Fifth. 'When they came out of the water and mud to us, looking like water rats, it was a truly pitiful sight. Many of them were killed in the pond and many were drowned.' The British had soon backed the Americans into a defensive position two miles across and about one mile deep on the shore of the East River. Fortunately for Washington, the winds had prevented Admiral Howe from sailing his fleet up the river and using his great firepower to wreak havoc with the patriots. The general knew only too well what would happen if the wind changed.

Despite the urging of subordinates who wanted to complete their victory, General Howe stopped his attack. Perhaps he feared a repeat of the costly and bloody 'victory' he had won at Bunker Hill. In a report to the British Parliament, Howe later said that the American army 'could be had at a cheap price,' meaning through a siege. Whatever Howe thought, his delay helped save Washington and the American cause.

Washington now called on Colonel John Glover of Massachusetts, who commanded one of the army's crack regiments. Glover's 'Marvelous Men from Marblehead' were well trained and wore smart blue-and-white uniforms. They were seamen and fishermen, so they were accustomed to shipboard discipline and were quick to carry out orders. As one Pennsylvania officer wrote, '[T]he only exception I recollect to have seen to the miserably constituted bands [Massachusetts regiments] was the regiment of Glover. There was an appearance of discipline in this corps.' Washington had used Glover and his men before. The Hannah, the first ship to sail in the service of the new United States, was Colonel Glover's own schooner, for which he found cannons and trained a crew and then successfully harassed British shipping and captured supplies for the Continental Army. In the wake of Hannah's success, Washington asked Glover for two more ships to create what became known as 'Washington's Navy.'

John Glover is truly one of the forgotten men of American history. Born in 1732 a few houses away from the building where the accused Salem witches were imprisoned four decades earlier, he was apprenticed to a shoemaker and later moved to Marblehead, where he saved his money and bought a schooner. As a mariner he earned enough to purchase more ships. He joined the Marblehead militia in 1759 and soon worked his way up to the rank of captain of a 'Military company of foot in the town of Marblehead.' By 1776 he had become the regiment's colonel. Washington knew that Glover was just the man to get his army out of its desperate situation. He also knew that there were spies in the ranks — one soldier had already been tried and hanged for his treachery and several others had been found guilty and put in prison — so he sent a misleading message to General William Heath on Manhattan: 'We have many battalions from New Jersey which are coming over this evening to relieve those here. Order every flat-bottomed boat and other craft fit for transportation of troops down to New York as soon as possible.' Then he ordered his quartermaster 'to impress every kind of craft on either side of New York' that had oars or sails, and to have them in the East River by dark. Anyone intercepting the messages would think that Washington was planning to bring reinforcements to Long Island; in reality he hoped to evacuate his entire army before the British realized what he was doing.

The weather was still on Washington's side. A drenching storm kept 'Black Dick's' fleet out of the river and provided cover for the boat gathering. Late in the afternoon Washington met with his staff to tell them his real plans. As Colonel Benjamin Tallmadge wrote in a letter, 'to move so large a body of troops with all their necessary appendages across a river a full mile wide, with a rapid current, in the face of a victorious, well-disciplined army nearly three times as numerous seemed . . . to present most formidable obstacles.' The colonel was guilty of understatement.

The August nights were short, and Washington knew that if Glover had miscalculated the time required for the Herculean job, he would lose any troops unlucky enough to remain on the island at dawn. He had faith in the 'tough little terrier of a man,' and to help him he assigned a regiment of men from the Massachusetts towns of Salem, Lynn, and Danvers, sailors all.

The seamen began their work as soon as it was dark, about ten o'clock. The drenched Continentals left their entrenchments unit by unit and moved to the boats in darkness and in absolute silence. Each unit was told only that they were being relieved and were going back to Manhattan. They did not know that the entire army was doing the same thing. By the time any disloyal soldier discovered the truth, it would be too late for treachery. The quartermaster's men had found only a few sailing craft, so there was much rowing to be done that night. At first the winds were favorable and the boats swiftly made the round trip to Manhattan, despite darkness and unfamiliar waters. Seamen in the rowboats plied them back and forth without a stop, oars muffled, across the fast East River current.

Washington stayed in the saddle, weary though he must have been. For several hours the situation looked favorable, but then the wind changed, blowing in combination with the unusually strong ebb tide. The sails could not overcome the two combined forces. Washington's despair was partially alleviated when the men rigged the sailboats with temporary tholes, found oars, and rowed. But the tired general realized that many rearguard troops would still be on the island when dawn broke. Their loss would be a serious blow. Yet the seamen continued their race against time. 'It was one of the most anxious, busy nights that I ever recollect,' Benjamin Tallmadge recalled, 'and being the third in which hardly any of us had closed our eyes in sleep, we were all greatly fatigued.' At one point a rearguard unit under Colonel Edward Hand mistakenly received orders to move down to the water. Its movement left a gap in the lines that the British, had they been aware of it, could have used to smash through the American defenses. But the British didn't know, and Washington, when he saw what had happened, hurriedly ordered the unit back into place.

In a few more hours luck rejoined the patriots. The wind changed direction and Glover's men could again use their sails to speedily make the crossings and return. The tempo of the evacuation picked up, but the fickle wind had done its damage. As the dim first-light appeared in the cloudy, gray eastern sky, part of the rear guard was still on the wrong side of the river. As the sky lightened, however, a dense fog rolled in, obscuring the operation's final movements. Colonel Tallmadge was in one of the last units to leave, and with regret he left his horse tied on the Long Island shore. Safe in New York, the fog as thick as ever, Tallmadge said, 'I began to think of my favorite horse, and requested leave to return and bring him off. Having obtained permission, I called for a crew of volunteers to go with me, and guiding the boat myself, I obtained my horse and got some distance before the enemy appeared in Brooklyn.' When the morning fog began to lift and the British patrols warily came to check on the American breastworks, they found them empty. Washington and the last of the rear guard were aboard the boats and sailing to safety. George Washington's faith in John Glover and the seagoing soldiers had been vindicated. In about nine hours they had whisked 9,000 men and their supplies and cannon out from under the noses of the British. The Revolutionary cause lived on. Later that day, August 30, 10 British frigates and 20 gunboats and sloops finally sailed up the river. They were too late.



This article was written by J. Jay Myers and originally published in the June 2001 issue of American History Magazine. For more great articles, subscribe to American History magazine today!

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12 Responses to “George Washington: Defeated at the Battle of Long Island”


  1. 1
    Larry Foss says:

    I am so proud to be an American, and to see the hand of Providence
    blessing us with a wind to keep back the British ships and a heavy
    fog to cover the last movements. If Washington and his men did
    not make this retreat that would have been the end for us. The weather again and again figures so prominently in aiding our side. Consider the morale-building battle of Trenton in having a frozen Potomac River to cross. Does anyone know how often the Potomac freezes?

  2. 2
    uncleSam says:

    i am doing a report on the americanrev, battle of long island. this is the hardest paper i've ever written but i"m learning the most.
    if anyone knows the answers to any of these questions commment back.<3

    1.how did gen. william howe& georgeW. explain their feelings towards the war or the enemy's leadership.
    2. how did they prepare for battle. (both men)
    3.what influence did wheather have?
    4.what strategy was followed. (both)
    5.what was the army's greatest advantage(both)
    6. detailed account of their movements.
    7. what impact did winning/losing have on them.
    8. how did it effect mood of soldiers.
    9. did it bring colonies closer to independence?

    THANK YOU times infinity.

    • 2.1
      Brian Stephens says:

      A little late for your paper, perhaps others could use this finding in the Quebec Gazette dated October 24, 1776: (transcribed as written)

      Extract of a letter from a Gentleman to his friend in this town, dated at Long Island, near New-York, August 31, 1776.

      The 22d the army landed on Long Island about 8 o'clock in the morning; I was permitted with a number of Gentlemen to land with them; as an idle spectator I had nothing to do but to observe the motions of the Army; the shore on which they landed was fine, nothing to obstruct them, the land flat and mostly clear; my being in one of the first boats, gave me an opportunity of seeing the whole Army as they landed and formed; the grenadiers and light infantry landed first and formed three columns and then the train of artillery; after that followed three brigades forming three squares behind each column to complete the disposition of this grand army; 5000 men brought up the rear, extending from right to left, the whole covered the plain four miles in length and three in breadth. To give you a more perfect idea of this grand appearance, I here prick down the columns, Artillery, Brigades, and Rear Guard, as I took them on the spot with my pencil. This Army consisting of 16000, all landed within two hours under the cannon of four men of war and two bomb ships, such was the warlike appearance of this army, that not only the Rebels who were stationed there to oppose the landing of the troops, fled, leaving all behind them without firing a shot, but the same panic seized the poor inhabitants, they ran with their wives and children, until the advance guard overtook them, and advised them to return to their homes, assuring them that they were safe while under the protection of the Royal Army. Never did a people more readily embrace an opportunity with greater pleasure; joy sparkled in every countenance. The army encamped about five miles from were they landed; four days past without anything being done, except a few skirmishes; in that time the troops landed their baggage, and made preparations for marching.
      We now come to the fatal day of the Rebels. the 27th the troops began to march; after they had advanced about two miles into the woods, they met the Rebels strongly posted on the height in the woods: a general engagement ensued, with the advanced part of our army, about 5000; the Rebels were 10,000, by the account of Lord Sterling and General O'Sulivan, who were taken prisoners, the Rebels were drove form post to post, until General Howe ordered them to halt, (meaning his own troops) biut by the number of the Rebels that were stopt, some lying prostrate on the ground, other standing like statues begging for mercy, one would suppose both armies were under his control; not less than 3000 were killed and taken prisoners. Our loss is inconsiderable; I do not chose to mention for fear of not being credited. I leave that to those who may have a more certain account. Thus they were completely beaten in their own way, to complete their disgrace.

  3. 3
    melissa says:

    what early defeats did the patriots experience? and why domyou think the patriots were defeated in New York?

  4. 4
    Susannabananauglylittleturd says:

    hahahahahha this is sooooooooooo inaccurate

  5. 5
    sam says:

    what the hell

  6. 6
    richmond says:

    what early defeats did the patriots face? (history but not in sports)

  7. 7

    [...] He valued life; he knew when to fight and when to walk away. [...]

  8. 8

    [...] to Historynet.com, "General George Washington knew he had badly [...]

  9. 9

    [...] to Historynet.com, "General George Washington knew he had badly [...]

  10. 10

    [...] to Historynet.com, “General George Washington knew he had badly [...]

  11. 11

    [...] to Historynet.com, “General George Washington knew he had badly [...]



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