Sunday, June 30, 2019

Episode 103: The Battle of Brooklyn

When we last left New York, General Howe commanded a combined force of about 32,000 British and Hessian soldiers on Staten Island, supported by his brother Admiral Howe, with over 10,000 sailors on over 400 ships.  The regulars had had time to recover from their sea voyages, and were in top condition after living on Staten Island for weeks, with plenty of fresh food and exercise.

Opposing them General Washington has less than 10,000 Continental soldiers and perhaps another 10,000 or so militia that might be available.  Even most of the Continental soldiers had no combat experience nor even much drilling for combat.  Most of the veterans of Concord and Bunker Hill had left the army at the end of 1775, replaced by new recruits.  As at Boston, disease continued to ravage the army, with smallpox, dysentery, and other diseases filling military hospital camps with nearly 6000 soldiers unfit for duty.  Among the sick was General Nathanael Greene who had been in command of the Long Island defenses until he fell ill.  In his place, Washington gave command to General John Sullivan, just back from losing Canada.

Washington’s army had spent the past nearly six months improving their defenses and anticipating possible enemy attacks.  Washington was not sure if the British would make a direct assault on New York City, or attack on Long Island or Northern New Jersey and then come at Washington from one of the sides.  The British fleet might also sail up the Hudson, land behind Washington's forces, and cut him off from retreat.  As a result, Washington spread his army all over the region to be ready for any of these possibilities.

Landing on Long Island

On the night of August 21, a brutal thunderstorm struck the region.  Witnesses reported a torrential downpour lasting over three hours, with nearly continuous lightning strikes.  Along the East River, a single strike killed ten soldiers encamped along the bank.  In town another strike killed three officers.  Dozens of homes caught fire and burned during the storm.  Many saw the violent storm as an omen of terrible things to come.

The next morning, the skies were clear and all had returned to normal.  British warships deployed along the coast of Long Island to cover the troop transports soon to follow.  The first group of 4000 soldiers under Generals Clinton and Cornwallis crossed from Staten Island to Long Island across Gravesend Bay, just south of where the Verrazano Narrows Bridge now stands.  The handful of Pennsylvania riflemen assigned to the area, fled without engaging the enemy, driving off cattle to deny them the enemy.

British Fleet in NY Harbor (from revolutionary-war)
The well planned landing went off flawlessly.  By noon the British had landed 15,000 men, with another 5000 still on the way.  Rather than attacking immediately, the British set up camp and began to establish defenses.  Again, they were in no hurry.

Back in New York, General Washington received reports that around 8000 British had landed at Long Island.  Concerned that this was still a feint, Washington kept the bulk of his forces in the city, prepared for a frontal assault. He deployed only around 1500 reinforcements across the East River to Brooklyn, bringing total the total number of defenders on Long Island to a little under 6000.  Washington also appeared to be unhappy with General Sullivan’s leadership, and the lack of order and discipline among the soldiers on Long Island.  On August 24, two days after the regulars had landed, Washington sent General Israel Putnam as field commander over Sullivan on Long Island.

For reasons, I have never completely understood, the British Navy did not bother to move up the East River.  If they had, they would have prevented Washington from deploying reinforcements and also cutting off the most obvious line of retreat for the forces on Long Island.  It could be that Admiral Howe feared damage from the shore batteries.  For several days, the winds blew unfavorably for moving up river.  Trying to run past the batteries against the wind might have been too great a danger for the fleet.

It could also be that the Howes did not want to cut off the lines of retreat.  That is why they also rejected General Henry Clinton’s plan to land forces up the Hudson River, north of the city, and cut off the Continental Army from any retreat.  Leaving open a line of retreat would reduce the will of the enemy to stand and fight.  If they took New York easily, perhaps the rebels would be more inclined to consider a negotiated peace.

Whatever the reason, the British took no action in the Hudson or East Rivers.  They landed their army on Long Island and set up camp.  Local Tories flocked to the army, greeting them as liberators.  Although the patriots had made some efforts to destroy crops and drive off livestock, there was still plenty for the regulars to enjoy.

The regulars also saw how well the colonists were living.  The standard of living in New York was far higher than that of most commoners in England or in the German States where the soldiers had grown up.  Many officers confirmed their views that the colonists were a bunch of whiners who did not realize how good they had it.  It made them all the more eager to crush this rebellion, and perhaps be rewarded with lands of their own in this prosperous countryside.

The Lines

For several days, the British Army camped on Long Island, in no particular hurry to do anything.  This gave Washington plenty of time to assess the numbers he faced and to send over additional reinforcements.  Even so, he only had a total of between 9000 and 10,000 soldiers to face over 20,000 attackers supported by navy cannons.  The Continentals concentrated the bulk of their forces around the forts they had built in Brooklyn.  They deployed only around 3000 inexperienced soldiers to defend the Gowanus Heights, the hilly defenses stretching along nearly six miles.

The Continentals had no cavalry to keep an eye on enemy deployments, and not much in the way of civilian spies willing to help them.  Washington still kept his best generals in New York, still fearing a direct assault on the city.  General Israel Putnam controlled Long Island from Brooklyn.  On the front lines, he relied on General Sullivan, who had never impressed him, and General William Alexander (Lord Stirling) who had only just joined the Continental Army.

The Continentals seemed to hope that the British and Hessians would make a frontal assault on their entrenched lines.  Even if they did overwhelm the American lines with superior numbers, Washington hoped they could be bloodied in the assault, just like they had done at Bunker Hill.

Jamaica Pass

In the British Camp, Washington’s hope seemed to be a realistic one.  General Howe seemed to favor a direct assault on the Continental lines, overwhelming the enemy and pushing them back against the East River.  Second in command General Clinton, though, had other ideas.  Clinton had grown up on Long Island when his father was governor of the colony.  He knew the land probably better than any other general on either side.

Map of British landing (from Wikimedia)
In evaluating the land and speaking with locals, Clinton discovered that the Continentals had placed defenses at the three mains passes through the Gowanus Heights.  But for some reason, they had left a fourth pass, known as the Jamaica Pass, unprotected, perhaps because they thought it was too far to the east and that no one would bother to go that far around.  Clinton decided it was the perfect place to move his army and then roll up the Gowanus Heights defenders from behind in a flanking maneuver.

Clinton was always proposing such flanking maneuvers and Howe always rejected them.  He had rejected such a plan at Bunker Hill and also a similar plan to attack New York City from behind.  Howe also rejected Clinton’s plan for Long Island. Clinton realized that arguing with Howe directly was pointless.  The two men had come to loathe one another, and Clinton’s reputation had taken a big hit after the his failure to accomplish anything during his brief independent command in the Carolinas.  Instead of arguing the point with Howe directly, Clinton sent several of his respected junior officers to plead with Howe to give more consideration to the plan.  Perhaps out of a fear of another Bunker Hill, Howe relented and gave Clinton permission to take his army out to the Jamaica Pass and run his flanking maneuver.

On the evening of August 26, Clinton led 10,000 soldiers, about half of the British force on Long Island, on the six mile march to the Jamaica pass.  To keep the march a secret, they took prisoner anyone they met along the way.  Unlike Massachusetts, Long Island did not have any patriot riders ready to alert anyone to the night march.  When they arrived at the Jamaica Pass, five Continental officers on horseback approached them, thinking they were Continental forces.  The British captured them without firing a shot.  Under interrogation, they learned that these five men were the only soldiers deployed to cover the pass.  By dawn, Clinton had led his army through the pass and had crossed the Gowanus Heights without encountering any enemy fire.

The Battle of Brooklyn

On the morning of August 27, General Howe deployed his remaining forces on a direct march against the rebel forces at Brooklyn.  The army moved forward slowly, with its lines in place by dawn.  British artillery opened fire.  British regulars and Hessians marched forward to test the Continental lines on the heights.  Lord Stirling commanded the Continentals defending the heights, among his soldiers were the famed Smallwood's Maryland Regiment and Haslet’s Delaware Regiment.  These were two of the Continental Army’s best equipped and trained regiments.  In both of their cases, their regimental commanders were missing, having been called to New York for court martial duty. But the regiments fought with distinction, along with others from Connecticut and Pennsylvania, 1600 Continental soldiers held back the advancing British and Hessians for hours.

Haslet's Delaware Blues on Long Island (from Wikimedia)
General Sullivan also arrived at the battlefield with additional reinforcements. For much of the morning, the enemy would approach within about 200 yards, but then pull back in the face of enemy fire.  The Continental officers were impressed with the ability of their army to stand toe to toe with the enemy in open field.

Then at around 9:00 AM, Howe fired a special signal gun, at which point Clinton’s forces, which had taken all of the Gowanus Heights defenders from behind, now descended on the main Continental forces at Brooklyn.  Sullivan and Stirling now faced not only 10,000 enemy in front of them, but another 10,000 attacking them from behind.  They eventually realized the British and Hessians in their front were not attempting to overwhelm them, but simply had been distracting them while Clinton’s army came around behind them.

The Americans defended themselves admirably in the face of the overwhelming assault.  Some soldiers covered the retreat of others, who had nowhere to go but into the Gowanus swamp.  Some drowned, but many eventually made their way back to the Continental forts at Brooklyn.

The Maryland regiment under the command of Stirling continued to hold off the enemy, giving other Continentals time to withdraw, but were soon overwhelmed.  The attacking Hessian soldiers attacked without mercy, bayoneting soldiers who tried to surrender.  The British did take hundreds of prisoners, including Generals Sullivan, Stirling, and Nathaniel Woodhull.  Stirling refused to surrender his sword.  Instead, he fought his way through the British lines to hand is sword to the Hessian General Von Heister.  I had not mentioned General Woodhull until now.  He was a militia general, not part of the Continental Army.  After his capture, an officer slashed him on his head and arm for refusing to say “God Save the King.”  The wounds led to an infection which killed him about two weeks later.

Washington crossed the East River from Manhattan to Brooklyn that morning, and worked with Putnam to restore order.  By 10:00 AM Washington and Putnam watched hundreds of fleeing soldiers straggling into their lines.  At the same time, the British Navy attempted to move up the East River, thus cutting off more reinforcements from New York and also the only line of retreat against the advancing British Army.

The Battle Ends

Then, around noon, with the British entirely in control of the field of battle, General Howe called a halt to the advance.  Many of the officers and men, wanting to push forward and deliver the final death blow to the Continental army, grew frustrated with the orders to stop pursuing the fleeing rebels.  Again, it is hard to guess Howe’s true motives, but the best argument is that he did not want to run uncontrolled into a concentrated and embedded enemy that could end up driving back the British or inflicting terrible casualties on the British as they overran the forts.

Despite ending early, the British had won the day by any measure.  They held the field that they planned to take, with only about 400 casualties.  By comparison the patriots had taken about 1100 casualties and about an equal number taken prisoner.


The next morning August 28, Washington found the remainder of his army facing the British lines, and with his back against the East River.  He brought over another 1200 reinforcements from New York, but even with reinforcements, he had only around 9000 soldiers while facing about 15,000 of the enemy with another 5000 or so in reserve.

The British began digging a series of trenches, moving slowly toward the patriot lines.  This was the traditional slow and safe way to take an enemy fort with a minimum of casualties.  With the numbers on their side, the British would almost certainly move close enough to blast the fort walls with their cannon and then take the fort if the patriots still refused to surrender.

Later in the day though, the weather changed.  A downpour soaked both sides.  They attempted to continue their fire at one another with increasing frustration at their waterlogged weapons.  The British continued to advance their trenches, slowly pushing toward the patriot position for a final assault.

The following day, August 29, it seemed like the continuing bad weather was the only thing holding back the final British assault.  If Howe managed to capture Washington’s 9000 man army that likely would have been the end of the war.  The remaining troops in New York almost certainly would have fled and scattered.
Thomas Mifflin
(from Wikimedia)

Washington held a council of war with his senior officers.  They agreed that they needed to retreat across the river to New York before the winds changed and the British Navy moved up the East River.  General Thomas Mifflin proposed the retreat, but also volunteered his Pennsylvania regiment to serve as the rear guard, meaning they would cover the retreat and be the last to leave Long Island.

The problem was getting an army of 9000 across the river without the British noticing.  Washington’s best bet would have been to have his men rush over the Brooklyn Bridge back to Manhattan.  The major flaw with that plan was that the bridge would not be built for another century, and they could not wait that long.  Rowing and army across the river in small boats in the face of the enemy would be nearly impossible.  Even if the navy could not move up the East River yet, Howe’s army could easily overrun the Continentals as they waited on the river bank.

They decided to move the men in secret that night, getting as many over as possible before the British discovered what they were doing.  Colonel John Glover’s Marblehead regiment, all experienced mariners, gathered all the boats they could find.  Washington issued orders that the men should be ready to move that evening for a night attack on the enemy.  Many soldiers thought it was crazy to mount a night attack, and were greatly relieved when they found out it was a ruse to keep secret the fact that they were being marched down to the river to retreat to New York.

Retreat from Brooklyn (from HistoryNet)
As soon as the sun went down, Glover’s regiment began ferrying the army across the river, starting with the wounded and least experience fighters.  Others kept campfires burning and made as much noise as possible so that the British would think the whole army remained in camp.  The wind and rain though, made crossing the mile wide river impossible.  The crews informed Washington that a they could not make the retreat.  Then, around 11:00 PM, the winds suddenly died down and they began transporting the troops back to New York.

Everyone worked in silence, the biggest fear being the British would discover the retreat and launch an attack on the remaining forces.  General Mifflin, still covering the front lines heard the British digging trenches all night, always moving closer toward the American lines.

Finally, around 4:00 AM a major came to inform Mifflin that they were ready to evacuate his troops.  Mifflin was shocked that Washington was able to get his army across the river that fast.  He even questioned the Major’s orders.  But the Major was adamant that the had just been over all the Continental lines and that Mifflin’s men were the last to go.  Mifflin took his troops down to the river, only to find that there were still thousands of soldiers waiting to cross.  Washington rode up and told Mifflin he had ruined everything.  By abandoning the lines, the British would realize the retreat was afoot and would march in and capture all the soldiers waiting to cross.

Mifflin, of course, angrily responded that he was following orders he was told were from Washington.  They soon realized the major had been mistaken in telling Mifflin to leave his post.  Mifflin marched his regiment back to the front lines, fortunately, without the enemy noticing its absence.

When dawn came, much of the army remained in Brooklyn waiting to cross.  At any moment, the British would discover the retreat and capture the remaining army, including Washington, who would not cross before the rest of his men did.  As the sun rose, the army experienced yet another miracle of weather.  A heavy fog set in, making it impossible for anyone to see more than a few feet in front of them.  The retreat continued that morning under fog, just as effectively as it did under the cover of darkness.

By early morning, Mifflin’s final regiment pulled off the line and crossed into New York.  Washington took one of the last boats across the river.  Within an hour of the final crossing the fog lifted and the British discovered the enemy had vanished.  All 9000 soldiers had escaped.  Although Washington had lost the battle, his army lived to fight another day.

Next Week: The Americans build a submarine and attack the British Navy.

- - -

Next  Episode 104: Submarine Warfare

Previous  Episode 102: Cherokee War in the South

Click here to donate
American Revolution Podcast is distributed 100% free of charge. If you can chip in to help defray my costs, I'd appreciate whatever you can give.  Make a one time donation through my PayPal account. 
Mike Troy

Click here to see my Patreon Page
You can support the American Revolution Podcast as a Patreon subscriber.  This is an option for people who want to make monthly pledges.  Patreon support will give you access to Podcast extras and help make the podcast a sustainable project.  Thanks again!

Further Reading


Kennedy, Roger The Battle For Brooklyn, 1776, Hudson Park Library, 2009:

Roger, J. David and Watkins, Conor Washington’s Escape from Brooklyn Heights Aug 1776:'s%20Escape%20from%20Brooklyn-Oct24-2006.pdf

Cohn, Benjamin The Legend Of General Nathaniel Woodhull, 2016:

Free eBooks
(from unless noted)

The Detail and Conduct of the American War, under Generals Gage, Howe, Burgoyne, and Vice Admiral Lord Howe, (original reports and letters) The Royal Exchange, 1780

Long Island in the American Revolution, NY State Am. Rev. Bicentennial Comm. (1976).

Adams, Charles Francis "The Battle of Long Island Vol 1", American Historical Review, 1896.

Carrington, Henry Battles of the American Revolution, 1775-1781, A.S. Barnes & Co. 1876.

Field, Thomas Warren The Battle of Long Island: With Connected Preceding Events, and the Subsequent American Retreat, Long Island Historical Society, 1869.

Force, Peter American Archives, Series 5, Vol 1, M. St. Claire Clarks, 1837.

Force, Peter American Archives, Series 5, Vol 2, M. St. Claire Clarks, 1837.

Fraser, Georgia The Stone House at Gowanus, Scene of the Battle of Long Island, Witter & Kintner, 1909.

Johnston, Henry The Campaign of 1776 Around New York and Brooklyn, Long Island Historical Society, 1878.

Martin, Joseph Plumb The Adventures of a Revolutionary Soldier, 1830 (This is a copy of the original print, but in poor quality.  You can borrow a better quality copy or listen to a free audio copy of the book).

Onderdonk, Henry Revolutionary Incidents of Suffolk and Kings Counties: with an account of the Battle of Long Island and the British prisons and prison-ships at New York, Leavitt & Co. 1849.

Smith Eugénie Marie Rayé The Battle of Brooklyn (Poem), National Society DAR, 1913.

Tomlinson, Abraham; Dawson, Henry B. New York city during the American revolution : Being a collection of original papers (now first published) from the manuscripts in the possession of the Mercantile library association, of New York city by New York (N.Y.). Mercantile Library Association;
Privately printed for the Association, 1861.

Ward, Samuel The Battle of Long-Island: a lecture, William Osborne 1839.

Books Worth Buying
(links to unless otherwise noted)*

Daughan, George C. Revolution on the Hudson: New York City and the Hudson River Valley in the American War of Independence, New York: W.W. Norton & Co. 2016.

Ellis, Joseph Revolutionary Summer: The Birth of American Independence, New York: Alfred A. Knopf, 2013.

Fleming, Thomas 1776: Year of Illusions, New York: W.W. Norton & Co., 1975.

Gallagher, John J. Battle Of Brooklyn, 1776,  Da Capo Press, 1995 (book recommendation of the week).

Grasso, Joanne S. The American Revolution on Long Island,  History Press, 2016

McCullough, David 1776, New York: Simon & Schuster, 2005.

Schecter, Barnet The Battle for New York, New York: Walker Publishing, 2002.

Wheeler, Richard Voices of 1776: The Story of the American Revolution in the Words of Those Who Were There, 1997.

* As an Amazon Associate I earn from qualifying purchases.

No comments:

Post a Comment