08/28/2026
This Week in 1776: August 28
THE GREATER GOOD
**The Revolution Nearly Ends in Brooklyn**
Seven weeks after declaring independence, the United States faced an uncomfortable discovery.
Declaring a nation was considerably easier than defending one.
On Aug. 27, 1776, British and American forces fought the Battle of Long Island, also known as the Battle of Brooklyn—the first major battle following the Declaration of Independence and the largest engagement of the Revolutionary War.
It went badly for the Americans.
British Gen. William Howe had landed thousands of British and Hessian troops on Long Island several days earlier. Gen. George Washington knew an attack was coming, but the wooded terrain and several roads through the heights surrounding Brooklyn made it difficult to determine exactly where.
Howe found the weakness.
During the night of Aug. 26, a large British force quietly marched east and then north through the poorly guarded Jamaica Pass. Local Loyalists helped guide them through the unfamiliar terrain.
By morning, British troops were behind the American left flank.
The result was devastating.
American units suddenly found themselves attacked from multiple directions. Some fought desperately to escape encirclement. Others were captured. Hundreds were killed or wounded, and more than 1,000 Americans were taken prisoner.
Among those who distinguished themselves were soldiers of the Maryland Line. A few hundred Marylanders repeatedly attacked a much larger British force near the Old Stone House, helping other Americans escape toward the defenses at Brooklyn Heights.
Watching the fighting, Washington reportedly asked, “Good God! What brave fellows I must this day lose!”
By the evening of Aug. 27, the surviving American army had retreated behind its fortifications at Brooklyn Heights.
And there it was trapped.
The British army stood in front of Washington. Behind him was the East River. British warships controlled the surrounding waters.
The revolution was barely a month old, and a substantial portion of the army defending it was in danger of capture.
Yet Howe did not immediately storm the American defenses.
Perhaps remembering the enormous British casualties suffered while attacking fortified Americans at Bunker Hill the previous year, he chose instead to tighten his siege.
That decision gave Washington something extraordinarily valuable:
Time.
During the next two nights, Washington would make one of the most consequential decisions of his career.
Rather than defend Brooklyn for political pride or sacrifice his army simply to demonstrate resolve, he would abandon the position.
On the night of Aug. 29-30, under remarkable secrecy and aided by favorable weather and fog, Washington's army would cross the East River to Manhattan. Thousands of soldiers, horses, artillery pieces and supplies would escape before the British realized what had happened.
It was not a victory.
It was something the young republic needed even more at that moment: survival.
The episode also revealed something about Washington that would become increasingly important during the war. He could learn from failure.
The Americans could not defeat the British by defending every city, road or hill at any cost. Britain possessed too many soldiers, too much money and overwhelming naval superiority.
Washington's most important responsibility was therefore not always to hold territory.
It was to preserve the army—and with it, the revolution.
That lesson reaches beyond military history.
The men who had signed the Declaration did not create a functioning republic on July 4. They created an extraordinarily ambitious political experiment that would survive only through adaptation, compromise, competent leadership and, occasionally, the willingness to admit that a plan had failed.
On Aug. 27, 1776, the United States suffered a crushing defeat.
But the American experiment did not require its leaders to be infallible.
It required them to recover from being wrong.