The British Flank: General Howe Traps Washington's Army at Long Island 1776

Added: 2026-05-30

[00:00:00]On August 26th, at 9:00 p.m., under cover of darkness, 10,000 British troops begin a night march toward the Jamaica Pass.

[00:00:10]It is one of the most audacious gambles of the war.

[00:00:13]The column stretches over 2 miles.

[00:00:16]An advanced party is led by Clinton, followed by Cornwallis, and General Howe.

[00:00:22]They leave their campfires burning behind them to deceive the Americans.

[00:00:27]If discovered, the whole operation would collapse.

[00:00:30]10,000 men strung out in the darkness on a narrow country road, unable to form battle lines, [music] left them vulnerable.

[00:00:39]But the Americans had no idea.

[00:00:42]Around 2:00 a.m. on August 27th, they reach Howard's Tavern, just outside the Jamaica Pass.

[00:00:49]British soldiers dragged tavern keeper William Howard and his son from their beds at gunpoint.

[00:00:55]General Howe needed a guide.

[00:00:57]William Howard refused.

[00:00:59]"We belong to the other side, General, and can't serve you against our duty."

[00:01:05]Howe's response was calm and cold.

[00:01:07]"You have no alternative. If you refuse, I shall shoot you through the head."

[00:01:13]Howard guides them to the pass.

[00:01:15]Minutes later, the four American militia guarding the pass are captured without a shot, mistaking the approaching troops as fellow Americans.

[00:01:24]General Howe has maintained the element of surprise.

[00:01:28]He has flanked the entire American army.

[00:01:31]Back on the east part of Long Island, at around 1:00 a.m., 4,000 British troops under General Grant launch a diversionary assault on Stirling's Marylanders at Gowanus Pass, holding them in place.

[00:01:44]Commanded on the ground by Major Mordecai Gist, twice the British attack the hill, and twice they are repulsed.

[00:01:52]At 6:00 a.m., in the center, Hessian artillery begin pounding the heights, but the German troops don't advance.

[00:01:59]They just sit there waiting.

[00:02:02]The Americans think Grant's attack is the main assault.

[00:02:06]General Sullivan sends 400 men west to [music] reinforce Sterling.

[00:02:10]The Americans think they are winning.

[00:02:14]Back in New York, Washington finally realizes his mistake.

[00:02:18]This wasn't a faint.

[00:02:20]He races across the East River to Brooklyn Heights to take command.

[00:02:23]By 7:00 a.m. Cornwallis's flanking column silently rounds the American position and crushes Colonel Miles's small force, scattering them instantly.

[00:02:34]Then at 9:00 a.m. the situation dramatically changes.

[00:02:39]General Howe fires two heavy cannons, the signal for the Hessian troops to begin their frontal assault against Sullivan.

[00:02:48]Soon the 10,000 British troops who'd marched through Jamaica Pass appear on the hilltops behind Sullivan's position.

[00:02:55]Panic.

[00:02:57]Sullivan's men are hit from two directions at once.

[00:03:00]Hessians in front, British regulars from behind.

[00:03:04]The line shatters instantly. Officers scream orders that no one could hear.

[00:03:09]Men throw down their weapons and run.

[00:03:12]Others froze, unsure which way to go, and are shot where they stood.

[00:03:17]The Hessians, driven by rumors that Americans take no prisoners, bayonet groups of surrendering soldiers.

[00:03:25]Major General Sullivan and many of his troops are captured.

[00:03:29]Private Joseph Plumb Martin, who witnessed the carnage, would later write, "The demons of fear and disorder seemed to take full possession [music] of all and everything that day."

[00:03:42]By noon, the American middle and left flank had been annihilated. [music] Thousands of Continental soldiers, disorganized, terrified, separated from their officers, [music] fled toward the only sanctuary left, the distant fortifications at Brooklyn Heights.

[00:04:00]But Cornwallis was faster.

[00:04:02]His elite regiments, the Black Watch of the 42nd Highlanders, and his Grenadiers, raced down Gowanus Road and seized the [music] Old Stone House, the last escape route.

[00:04:14]Thousands of American soldiers are trapped in what is known as >> [music] >> the killing box.

[00:04:20]Behind them, Gowanus Creek, a tidal salt marsh, where the mud could swallow a man to his chest. In front, Cornwallis and 2,000 veteran British soldiers blocking the only road to safety.

[00:04:35]On their flanks, 25,000 more enemy troops are closing in.

[00:04:40]Major Gist recounts, "Surrounded on all sides, the result was a bloodbath as the Hessians and British Highlanders methodically gave no quarter or mercy."

[00:04:53]The American Revolution, just 52 days old, is dying on a Brooklyn battlefield.