New York was LTG George Washington’s nightmare: the city was on the southern tip of Manhattan Island and dominated by the western tip of another island, the Brooklyn Heights on Long Island, and he had no navy. In July, Washington politely rejected Lord Howe’s offer of pardons, just after Howe’s adjutant pointed out these exact inconvenient facts. He also dismissed Nathaniel Greene’s suggestion to burn the wretched hive of loyalists to the ground and fight somewhere else. Washington understood that the Continental Army had to be seen defending all Americans, not just particular groups. Despite the difficulties, a defense of New York would at least be attempted. Washington had 22,000 men but Howe had 35,000 so he split his army: half on Manhattan, 1/10 in forts blocking the Hudson (Forts Lee and Washington. We will speak of them later), and 2/5 on Long Island.
On 21 August 1776, Washington’s spy network determined that Brooklyn would be Howe’s next target. That night Washington rushed reinforcements to Long Island, where MG Sullivan discerned that the best place to meet Howe would be the Guan Heights south of Brooklyn Village. The Guan Heights were a series of hills and passes which was thought would negate Howe’s advantage of superior numbers. But the defensive preparations were muddled. It was clear that Washington and his subordinate commanders and staffs were still having difficulty with all aspects of running the army, particularly one so large as the Continental Army in the summer of 1776. The three western passes were defended, but far to the east, the Jamaica Pass, was thought too far away for use by the British. They were wrong.
On 22 August the first British and Hessian troops landed at Gravesend Bay on Long Island. By 25 August Howe had 20,000 men on the island. On the evening of 26 August, Howe led a night march of 10,000 guided by loyalist farmers around the American defenses through the Jamaica Pass. At 0300, Cornwallis and Clinton attacked the Guan Heights to fix Washington, and at dawn Howe crashed into Sullivan’s unprotected flank and rear. The entire left of the Continental Army broke. Washington ordered a retreat for the fortifications of the Brooklyn Heights but the entire army was in chaos. That so many men would escape was solely the result of the defense and counterattacks of the 1st Maryland Line, led by MAJ Mordecai Gist, known to history as “The Maryland 400”.
MG William Alexander Lord Stirling, in command of the Washington’s right on Battle Hill thought he was winning the day against the Hessians and Royal Marines to his front until British regulars appeared behind him. He ordered most of his troops back but stayed with Gist and the rearguard of Marylanders. The Maryland 400 had never been in a fight together before that morning and took on 2500 British and two cannon. They alternated between breaking up attacks and counterattacking with bayonets, which they did six times, twice to capture an old stone house, before being destroyed. 256 Marylanders were killed, the rest wounded and captured, including Gist and Stirling. Washington watching from a nearby hill, said of them “Good God, what brave fellows I must this day lose.” Only twelve made it back to the Brooklyn Heights.
That afternoon, Washington and his commanders scrambled to reorganize the shattered army to defend the Brooklyn Heights for Howe’s inevitable assault that evening.
But it never came. Nonetheless, as soon as the Royal Navy entered the East River the next morning, Washington would be trapped, and there was nothing he could do about it.