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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: