The Battle of Long Island

By Gabriel Smith

War is a mixture of brutal violence and a duel of the mind, one does not simply fight their way through a battle nor does one simply give orders. Both the mind of the officer and the might of men must work in unity to defeat an enemy of any strength. While the incompetence of one of these two core sides of war can be overcome by an excess of the other, when facing an enemy of greater skill and strength there is little room for the errors of an officer or the cowardice of those he commands. General George Washington had seen failures by those in command and had seen the cowardice of men but at the battle of Long Island, he would see both failures of command and cowardice of man on a level so high that it would nearly crush him and his army.

George Washington was a wise general, he knew that New York had to be held for the revolutionary cause to succeed. The British knew this also, and they set about to deal a crushing blow to the rebels.

In late April, Washington arrived in New York where he split his 20,000 man force in two, positioning over half on Manhattan Island and the remaining soldiers on Long Island. Washington believed that the main attack would most likely come on Manhattan Island, but even after positioning his men, he was still unsure if he had judged correctly.

Would the British indeed attack Long Island? Who could know?

Washington knew that even if the main attack came on Manhattan Island that Long Island could be used by the British to shell New York City and thus could not fall into the hands of the enemy. Knowing this, Washington put the very capable General Nathaniel Greene in charge of holding Long Island and ordered troops on both islands to dig in.

On Long Island, the region of hills known as the Brooklyn heights was to be the main position of defense. In the Heights, there were four roads that would allow enemy advancement. These roads thus had to be blocked. Three of these roads were blocked well but the fourth, known as Jamaica Pass, was guarded by only a small force of horsemen, which had little chance to be able to hold out against a British assault. Why did Washington choose to not fortify Jamaica further? Perhaps he expected any British assaults on the island to come towards other positions on the line, or maybe he thought that the position could be held with the force he had placed there.  

The British General William Howe positioned himself on Stanton Island. Howe got wind of the weakness on Jamaica Pass from people loyal to the British cause. This information would be vital to his planning for the battle.

On August 22, Howe lands 20,000 men on Long Island and prepares to assault the rebel positions. Green is out with illness and the British army does have greater size and greater experience than the American forces but there is little excuse for what was about to happen. 

The attack began on August 27. Howe splitting his men into three columns, the left and center engaging the Americans forced them to shift positions. The British right column, consisting of 10,000 men, found, as they had been told, Jamaica Pass practically unguarded. The right British column then advanced and attacked the American rear. The Americans surprised by the sudden attack ran in droves, a mere few standing to face the British advance, and those slaughtered. It was in this moment that Washington, now on Long Island himself, began to beat his own retreating officers with the blunt side of his saber yelling for them to stand and fight, but to little avail. The revolutionaries had failed.

If Long Island had been lost against greater odds this failure may have not looked as bad, but it had appeared as if the revolutionaries had actually stood a chance against the British. The Americans were not untrained militia anymore, and they had defensive positions. This battle would have been a much easier victory than many of the other battles Washington had and would engage in, yet somehow the revolutionaries lost. 

It was at this moment when the future of America could have collapsed. Washington could have let panic overtake him and the army could have been lost, but the mental fortitude of Washington and the patriotism of those few who stood saved the very nation. Then, Washington pulling his men back positioned them for battle. 

Along with the success of Washington and his men, Howe made the mistake of not pushing the attack. For the next two days, Howe would reform his men preparing for a final assault of the American positions.

Maybe Washington had lost the battle but he would not lose his army, he at this moment managed to perform one of the greatest retreats in American history. 

A storm arrived on the night of the 29th and Washington enacted his bold plan. Leaving a skeleton force of brave patriots behind to give the appearance of a desperate stand Washington, under the cover of the storm and darkness, snuck the majority of his army, most of which could not swim, to Manhatten Island by boat.

While the American army had failed in many ways and many lives were lost, along with the whole of the battle itself, in the end, General Washington, his officers, those who had stood their ground in the initial fight, and those who had remained bravely on Long Island so that their comrades could keep up the fight, had saved the army and in doing so they had saved the whole of the nation. 

Battlefield Map


Retreat at Long Island. Engraving by J.C. Armytage from painting by M.A. Wageman. 148-GW-l74