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Lessons from the Battle of Long Island
The appearance of a British fleet in the waters off Long Island in late June 1776 did not come as a surprise to Continental Army Gen. George Washington. The size of the fleet did, however.
Three months earlier the king’s army had evacuated Boston after unsuccessful attempts to suppress Patriot forces in the area. Bloodied during their return march from Concord and decimated by their pyrrhic victory at Bunker Hill, British Maj. Gen. Sir William Howe and his 9,000-strong army had sailed to Halifax, Nova Scotia, to regroup.
Washington had correctly assumed the British would next target New York City, and he redeployed the army accordingly. Unfortunately, from Washington’s perspective, Manhattan was difficult to defend—especially against an enemy with unchallenged amphibious capability. Essential to its defense was Brooklyn Heights, prominent Long Island high ground on the opposite bank of the East River overlooking the city, the river and the harbor.
On July 2 the vanguard of the British fleet began disembarking on Staten Island. By mid-August Howe had landed an army of 32,000 British and Hessian troops. Reinforced by militia units, Washington commanded scarcely 20,000 men in and around New York City. He split the force, sending half of the army to Long Island under Maj. Gen. Nathanael Greene. He began fortifying Brooklyn Heights but fell ill and was replaced by Maj. Gen. Israel Putnam, who was unfamiliar with the Long Island terrain. On August 22 Howe led more than 15,000 men and 40 artillery pieces across the Narrows from Staten Island to Long Island, coming ashore unopposed just 7 miles from Brooklyn Heights.
Keeping most of his 10,000-strong army atop Brooklyn Heights, Putnam pushed out strong covering forces of some 3,000 men along a ridge 2 miles south of the main position. Passes through the ridge were identified and covered—with the exception of Jamaica Pass, on the far east end of the American position. Local Tories informed Howe, who led 10,000 men at night through the pass and into position on the American rear and left flank. Howe launched a single massive assault on the morning of August 27. Patriot forces were overwhelmed.
Howe’s forces swept to the base of Brooklyn Heights, from which Washington observed the unfolding disaster. The Americans had lost more than 2,000 men (1,000 captured), while British losses were around 400. At that point, however, Howe halted the attack. Likely shaken by the sharp British losses at Bunker Hill and unwilling to risk an immediate assault, he opted instead to besiege the cornered Patriots.
Two days later Washington took advantage of darkness, fog and bad weather to ferry his surviving men and most of their materiel across the river to Manhattan. Though outgeneraled, outmaneuvered and outfought, Washington extracted most of his army, thus saving it and the Patriot cause.
Know the terrain. When your enemy knows more about the terrain you occupy than you do, expect the worst. Putnam’s dereliction regarding Jamaica Pass led to a rout of the entire forward position.
A reeling army will respond to inspired leadership. Washington steadied the survivors of the routed covering force, stabilized the position atop Brooklyn Heights and snatched his army from the jaws of destruction through his successful retreat across the East River.
Beware of applying previous “lessons learned.” Howe’s fears of another Bunker Hill–style bloodletting stayed his hand. He forfeited the opportunity to possibly bag the Patriot forces (including Washington) on Brooklyn Heights and end the Revolutionary War that afternoon. MH
This article appeared in the November 2020 issue of Military History magazine. For more stories, subscribe here and visit us on Facebook:
The Battle of Long Island
The battle of Long Island, a British victory, began just after the Siege of Boston. As the British fled from their defeat, General George Washington anticipated they would go south and try to attack New York. He and his army traveled southward, in an attempt to cut them off before the attack.
As it turns out, the British had fled North and camped out in Halifax, Nova Scotia. They continued North, reaching the Hudson River on June 29, 1776. Four days later British General William Howe arrived on Staten Island to prepare an attack. The next day (July 4, 1776) was the day that the America’s Continental Congress declared the independence of America.
The Delaware Regiment at the Battle of Long Island | Public domain image.
While all of this was happening, George Washington had been preparing for battle in New York. He had created a wall of men with guns to defend the city from any attacks from the sea and placed 10,000 men on Brooklyn Heights to defend Manhattan. He was ready for anyone who would attack New York. There was just one problem: the British would be attacking Long Island, not New York.
On August 27, 1776 the British landed on Long Island, which is south of New York. Two days later, General Howe learned that the Americans had no one guarding the road leading North from Long Island into New York, but had defenses set up on all the other roads.
“The British fleet in the lower bay” depicts the invasion fleet under Admiral Howe assembling in lower New York Harbor in the summer of 1776, in preparation for the Battle of Long Island.
Using this information, Howe led his men up the North road. He then proceeded around to attack the Americans guarding the left road, who were led by General John Sullivan. While Howe’s army attacked Sullivan’s from behind, a German troop, which was in league with the British, attacked from the front. Sullivan fought as well as he could, but he was soon overpowered and forced to retreat behind the Brooklyn walls.
Howe, feeling proud of his victory, led his men and attacked the men guarding the right road, using the same technique. They, like Sullivan’s men, fought hard but were forced to retreat to Brooklyn.
On August 28, Washington heard of this attack and, in a panic, tried to come with reinforcements. However, the British forces were too strong and they forced the Americans to evacuate the city of Brooklyn entirely. In a frenzy, the American army fled. General Howe, blinded with pride, let them escape, thus missing an opportunity to take General Washington captive.
Later on that month, the British attacked New York and the Americans were once again forced to evacuate. Howe let yet another opportunity to take Washington captive pass, and this time he could have taken most of the American army as well. Had he done this, he might have greatly changed the outcome of the war.
George Washington and the Battle of Long Island
In the summer of 1776 the British Monarchy sought to put a quick and decisive end to the rebellion in the American colonies. King George sent the British Navy, the most powerful military force the world had ever known, to destroy the upstart army of George Washington. News that the colonists had officially declared independence only steeled the English resolve against the rebels who they saw as supremely disloyal to England and the Crown.
The British Arrive In New York
General William Howe was in command of the huge armada that began arriving in New York in early July. The thousands of British and Hessian troops on board found themselves welcomed by American loyalists who were living a comfortable life and who did not side with the rebels in the fight for independence.
Howe’s adversary, George Washington, challenged him with an army made up of American citizens who had no formal training or experience at soldiering. Washington himself had never commanded an army on the battlefield and in addition to being inexperienced, many of the soldiers he depended on were sick due to disease and poor hygiene. General Howe was confident the fight against the rebels would be decisive and victory swift.
The British Buildup on Long Island
Throughout July and into August, more and more British warships sailed into American waters. While Washington was aware of the odds against him, he felt New York had to be defended against the British invasion or the Continental Army would have no credibility. Convinced Howe’s true plan was to attack Manhattan Island, Washington split his forces, leaving about half of his 18,000 troops on Manhattan while the other half manned fortifications in Brooklyn on Long Island.
The buildup of British forces arriving by ship continued until Howe had over 20,000 troops at his command. On August 22 the English invaders stormed the beaches of Long Island uncontested by Washington’s army. There they established a huge encampment where Washington was able to observe them during an inspection visit he made of his own troop fortifications in the Brooklyn heights four days later.
Washington was appalled to find his forward lines unguarded and reprimanded his general, Israel Putnam for the overall lack of discipline displayed by the troops. Things did not bode well for the Continental Army.
The Battle of Long Island
Washington’s misgivings about the readiness of his men was confirmed when General Howe, employing a plan devised by General Henry Clinton, attacked the American army’s positions in Brooklyn under cover of darkness during the early morning hours of August 27.
The British General James Grant attacked the Americans on their right flank while the Hessian General von Hiester fired his artillery at the center of the American lines. At daybreak the remainder of Howe’s soldiers caught the Americans off guard by attacking from the rear. The Hessians charged forward and the inexperienced Continental Army having to deal with highly trained, professional soldiers, was routed into a disorganized retreat.
It was only after hearing about the early morning British attack that Washington sent his troops stationed on Manhattan Island to reinforce those on Long Island. But it was too late. Washington and his army had suffered a terrible defeat in a battle that had lasted about six hours.
The remaining soldiers of the Continental Army regrouped at the Brooklyn fortifications where they expected the British to make a final attack and finish the job. But General Howe, proving to be a cautious commander, chose to regroup his own forces before pursuing the rebels.
This decision allowed Washington the opportunity he needed to make a daring evacuation from Long Island to Manhattan, saving the Continental Army and America’s fight for independence.
The Battle Begins
On August 27, just after midnight, Grant led his 5,000-man column north along the Gowanus Road and began skirmishing with the Patriots.
At 3:00 A.M., Putnam was told of the British movement and he ordered Alexander to advance to the far right with reinforcements. Alexander deployed about 1,600 troops to meet Grant's troops. Grant stopped in front of the Patriot line and began firing his artillery. Meanwhile, Gen. Sullivan had reached the center of the line near Flatbush Pass, where he found Gen. von Heister's Hessians firing artillery. Sullivan sent troops west to reinforce Alexander.
At 8:00 A.M., Washington arrived on Long Island. When the British attacked the Patriot right and center, Colonel Samuel Miles moved west toward the attacking British. This left the Jamacia Pass without any defenders. Learning that the pass was not defended anymore, Miles was ordered back. He arrived just in time to spot the tail end of Howe's column of baggage trains moving through the pass. Realizing the dangerous situation, Miles sent half of his men (250 troops) toward the main line to warn them and escape. With the other 250 troops, Miles attacked the baggage train. Almost all of them were captured, including Miles.
At 8:30 A.M., the British turning column reached Bedford. They had managed to march completely undetected behind Putnam's line.
At 9:00 A.M., Howe fired a pair of signal guns to alert Grant and von Heister to attack the front of the heights while Howe advanced against the rear. Unfortunately for Howe, only von Heister made their attack. He moved north up the main road in the middle of the battlefield. He ran into Sullivan's troops and attacked them. Within a few minutes, the Patriot line unraveled as the troops fled to the main Brooklyn line. Sullivan organized many of his men and made a defensive stand at Baker's Tavern. They were soon captured by von Heister's Hessians.
Battle of Long Island 1776
By 11:30 AM, Alexander's troops were overwhelmed by Grant's superior numbers. Grant had moved forward in a decisive attack that broke apart the Patriot line. Most of the Patriots tried to escape and fled toward Gowanus Creek. When Alexander learned that General Charles Cornwallis was blocking his retreat, Alexander launched a series of counterattacks with about 250 Maryland troops, commanded by Major Mordecai Gist. Unable to clear a large enough path, most of the Patriots, including Alexander, was captured.
After sweeping Putnam's troops off the Brooklyn Heights high ground, Howe's senior commanders wanted to continue their advance and attack the last line of Patriot defenses. Instead, Howe halted his troops, reorganized his command, and ordered entrenchments dug facing the Patriot defensive works. With control of the East River, he believed that Washington was trapped and had nowhere to go.
On August 28, severe rain storms prevented any fighting between Washington and Howe. Both sides stayed in place. Also, because of the high winds, Howe was unable to move his warships behind Washington's position.
On August 29, during the evening, Washington called a council-of-war to consult on the proper measures to be taken. It was determined that moving across the river was the only way to escape. He ordered that all boats that could be found to be gathered up. The plan was to use the boats to ferry his troops across the river to safety. This way, they could escape the British trap and withdraw undetected from Brooklyn Heights. A heavy rain and fog kept the Patriot escape from being seen from Howe. Heavy winds continued to keep the British ships from advancing to Washington's position.
The Battle of Long Island
The withdrawal started soon after it was dark from two points, the upper and lower ferries, on the East River. The intention of evacuating the island had been so prudently concealed from the troops that they did not know where they were going. The field artillery, tents, baggage, and about 9,000 men were conveyed over East River, more than a mile wide, in less than 13 hours. Being only 600 yards away, Howe and the British army had no knowledge of the Patriot withdrawal that was proceeding.
On August 30, around 6:00 AM, the last of the Patriots left the shore of Long island. The withdrawal had worked without the British finding out.
At 11:00 AM, the heavy winds finally died down enough for the British warships to begin to move upriver.
At 11:30 AM, the fog lifted. Howe ordered his troops to advance and take the Patriot works. When they arrived, they discovered that the Patriots were nowhere to be seen. Howe realized that he had let Washington and the Patriots slip through his grasp. The British warships were finally able to move upriver, just a few hours too late to stop the Patriots. If Howe could have captured Washington and his troops, this would have effectively ended the war.
The defeat at Long Island cost Washington 312 killed, 1,407 wounded, and 1,186 captured. Among those captured were Lord Stirling and Brigadier General John Sullivan. British losses were a relatively light 392 killed and wounded. A disaster for American fortunes in New York, the defeat at Long Island was the first in a string of reverses which culminated in the British capture of the city and surrounding area. Badly defeated, Washington was forced retreat across New Jersey that fall, finally escaping into Pennsylvania. American fortunes finally changed for the better that Christmas when Washington won a needed victory at the Battle of Trenton.
Battle of Long Island - HISTORY
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"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 houses and farms are to be pillaged and destroyed, and themselves consigned to a state of wretchedness from which no human efforts will deliver them. The fate of unborn millions will now depend, under God, on the courage and conduct of this army. Our cruel and unrelenting enemy leaves us only the choice of brave resistance, or the most abject submission. We have, therefore, to resolve to conquer or die."
Address to the Continental Army before the Battle of Long Island | Tuesday, August 27, 1776
When Washington deliver this address, his soldiers could look out into New York Harbor and see the largest British expeditionary force in that nation's history until the First World War. With the United States having recently declared formal independence, the stakes for the Continental Army soldiers could hardly have been higher.
4. Makeup of the Forces
The Battle of Long Island was fought between the British and the American Armies. It was the first battle that involved the American Army after the independence. The British army was under the command of Major General William Howe while the American troops were under the command of General George Washington. The British troops numbering 34,000 were under the operational command of Sir Henry Clinton and Major General Charles Cornwallis. The British also got reinforcement from the Hessian troops.
6 The Battle of Long Island Decided by Sudden, Inexplicable Fog
On Aug. 27, 1776, just weeks after the signing of the Declaration of Independence, the British forces already had George Washington and his Continental Army on the ropes in New York City. There was no escape across the East River, as the Brooklyn Bridge hadn't been invented yet, and the water was thick with British warships -- the start of a long tradition of the East River being full of debris.
As the British closed in, it looked very much like the American Revolution was over just a few weeks in.
The weather took an unseasonable turn for the worse in New York on Aug. 29, and for the Continental Army, this seemed like another element to add to a long list of grievances, being that they were trapped, outnumbered, ill-equipped, poorly trained, freezing and starving, and it was raining. It seemed as if God was punishing the Americans with the same weather that usually makes everyone hate England in the first place.
But this rain turned out to be one of the best-disguised blessings in history, as it was so foggy the next morning that one could "scarcely discern a man from six yards' distance," which meant the Brits had to sit on their thumbs until the fog passed. What was more, for some freak reason, the fog "concealed from the British the operations of the Americans, while at New York the atmosphere was perfectly clear." In other words, the only parts of the city that were foggy were the parts the Brits needed to see through to figure out what the hell Washington was up to.
Washington did not need to shoot the British the next morning he just needed to get the hell out of Brooklyn with enough of his army to continue and win the war with. This fog provided him with precisely the time and the cover he needed to successfully sneak all 9,000 of his men into Manhattan while the British sat back and reminisced about this jolly good London weather. It was like Washington shouted, "Cover me!" at God, and God had complied like world's greatest buddy cop. There was not a single loss of life, and Washington was the last one to leave Long Island . immediately after he snatched his whole army and the Revolution straight out of the British Empire's back pocket.
December of 1776
December 7, 1776 at Tappan, New York
On December 7, a force of Tories and British marauders, known as "cowboys," pillaged the town of Tappan. They tormented local patriots and cut down their liberty pole.
Conclusion: British Victory
December 8, 1776 at Newport, Rhode Island
Gen. Sir Henry Clinton, under orders from Gen. William Howe, who had found Clinton's insistent advice aggrevating, sailed into Newport with 6,000 soldiers and took possession of Newport without any resistance.
Conclusion: British Victory
December 13, 1776 at Basking Ridge, New Jersey
On December 12, Maj. Gen. Charles Lee made camp a few miles south of Morristown. He was on his way to join Gen. George Washington's force. For reasons unknown, Lee did not stay at the camp but instead, he went to White's Tavern near Basking Ridge, about 3 miles from the American camp. Lee brought along a guard detachment of 19 troops with him.
Gen. James Cornwallis had learned that there was an American force close to his rear. He sent a cavalry detachment to patrol from his headquarters at Pennington, which was about 30 miles south of Lee's camp, to locate the American camp. Lt. Col. William Harcourt, with 29 cavalrymen from the 16th Light Horse and Lt. Col. Banastre Tarleton, headed north that night.
On December 13, after a brief rest, the British patrol headed towards Morristown. When they were about 5 miles from Basking Ridge, a local Tory gave them information that stated where the location of the main American camp was. After capturing 2 American sentry's, they sentry's told Harcourt that Lee and his guard detachment were located at the tavern.
Not knowing if this information was correct, Harcourt sent Tarleton and 2 cavalrymen to a small hilltop nearby for some observation. Once Tarleton captured an American soldier and reported back to Harcourt, stating that the information was indeed correct.
At 8:00 A.M., Lee ordered his force to move forward but he stayed back at the tavern to finish some paperwork.
At 10:00 A.M., just after finishing up his paperwork, the British attacked the tavern from 2 sides. The British overwhelmed the guard detachment, which lee observed from an upstairs window. The British then opened fire on the tavern. Lee had waited for 15 minutes before deciding to send his Aide de Camp, Maj. William Bradford, to the door to give himself up.
The British gathered up the wounded and the prisoners and headed back to Pennington. They forgot to search the tavern and a few American soldiers escaped and returned to the American lines, informing Washington of Lee's capture. A search party was sent but by this time, the British forces had lee back at their headquarters.
Conclusion: British Victory
December 15, 1781 at Hackensack, New Jersey
Gens. William Heath and George Clinton raid Hackensack, snaring several British soldiers and arresting 509 Loyalists. A quantity of military supplies is also removed before British reinforcements arrive.
Conclusion: American Victory