08/27/2026
On this date in 1776 - The Patriots Lose the Largest Battle of the Revolutionary War
Following the British retreat from Boston in 1776, George Washington knew it was only a matter of time before the enemy headed to New York. While he urged his soldiers to strengthen their batteries and build forts to repel the British, his fatal mistake was stretching and dividing his fighting forces. He split his army into two: one protecting Manhattan and the other protecting Brooklyn.
The British had 20,000 forces, while the Continental Army only had half that number. With the army halved, they couldn’t defend the Jamaica Pass, a rarely used path between a formation of hills that the British had heard from Loyalists was unguarded. The British attacked on two fronts. One half of the battle happened at Brooklyn Heights while a Hessian general attacked the Heights of Guan.
On August 27, British soldiers began firing on American soldiers near the Red Lion Tavern in Brooklyn. Washington’s generals realized they were surrounded, and ordered retreats, else the entirety of the Continental Army would be captured. British General Howe smelled victory and ordered his men to dig a trench around the American army. It was then that Washington made the difficult decision to evacuate Long Island, forfeiting the city to the British.
As the soldiers rowed across the river, fortune smiled upon the Continental Army, and a fog settled over the water, allowing them to escape unseen by the British. When the British begin probing the American lines, they found that Washington’s army had vanished.
While losing New York was devastating, Washington’s decision to retreat was the only thing that saved the Patriot cause. Had he not ordered the retreat, the entire army would have been forced to surrender, the British would have effectively won the war, and the United States would not exist today.
📷 Battle of Long Island, a National Guard Heritage Painting by Domenick D'Andrea, courtesy the National Guard Bureau.
