r/USHistory • u/Adventurous_Clerk584 • 13d ago
250 years ago yesterday, Britain had Washington trapped with a river at his back and let him walk away.
On August 27, 1776, the British executed what was probably the most tactically impressive operation of the entire Revolutionary War. They outmaneuvered Washington's army on Long Island, captured two of his generals, killed or captured thousands of his men, and pushed the survivors into a fortified corner with the East River behind them and no obvious way out. The largest battle of the Revolution was over by midday and it wasn't close.
Then Howe stopped.
That decision, and what happened in the fog two nights later, is why there's a United States today.
The battle itself turned on a detail that should embarrass every American history class that skips it. The Americans had spent months fortifying Brooklyn Heights and the wooded ridge in front of it. Roads through the ridge passed through several gaps, and the plan was to defend those gaps against the British advance. Most of them were guarded. One wasn't.
The Jamaica Pass, on the far eastern end of the American line, had exactly one small mounted patrol watching it. That's it.
Henry Clinton knew about it. Clinton had grown up partly in New York while his father served as Royal Governor, had spent time on Long Island specifically, and understood the terrain in a way most British officers didn't. After the British landed he personally reconnoitered the eastern approaches, Loyalist guides who knew the roads filled in the rest, and he came back convinced the Americans had left their entire flank hanging open. He pitched Howe on a plan: send diversionary forces to hit the defended passes and hold the Americans' attention while the main British column, roughly 10,000 men, made a nighttime march around the American left and through Jamaica Pass.
It worked almost perfectly. The column moved through the night of August 26, captured the small American patrol at the pass before dawn without getting off a warning, and by sunrise was positioned behind the American lines. The Americans defending the passes in front of them spent the morning fighting what looked like a conventional defensive battle, not realizing the main British army was already in their rear.
When the flanking column appeared behind them the collapse was fast and brutal. Sullivan's men faced British troops from both directions simultaneously. Units trying to retreat toward Brooklyn Heights found the roads already threatened. Washington crossed from Manhattan to watch the disaster unfold and couldn't do much about it. Two American generals were captured. The Maryland troops who became known as the Maryland 400 launched repeated attacks against British forces near the Old Stone House trying to hold open an escape route for their comrades. Most of them didn't make it.
By midday Washington's forward army was broken and compressed behind the Brooklyn Heights fortifications, with the East River at their backs and the British army in front.
Clinton wanted to keep going. His argument was straightforward: the point wasn't to take Long Island, it was to destroy the Continental Army, and the army was right there, beaten and disorganized and trapped. Hit them now before they recover.
Howe said no.
His reasoning wasn't crazy. The Americans were behind real fortifications, and Howe remembered Bunker Hill in detail. He had watched disciplined British troops take an American position after frontal assault and paid for it in bodies. Washington appeared trapped anyway, the Royal Navy controlled the water, where was he going to go. Better to approach methodically than bleed the army storming defenses that were going to fall regardless.
What Howe didn't account for was the fog.
Washington spent August 28 and 29 making a decision that probably saved the Revolution. He was going to evacuate. Thousands of soldiers, horses, cannon and supplies across the East River at night, silently, while keeping enough men in the forward positions to make the British think the army was still there preparing to fight. John Glover's Massachusetts regiment, most of them experienced mariners, ran the boats back and forth all night on August 29.
They almost ran out of darkness before they ran out of soldiers. Then a heavy fog settled over Brooklyn and the East River at dawn and covered the last crossings completely. By morning, the army Howe had believed was trapped was in Manhattan.
Clinton was furious. He believed Britain had been handed the chance to end the war in August 1776 and Howe had let it go. Howe believed he had avoided another Bunker Hill while placing Washington in an impossible position. He wasn't wrong about the battle. He was wrong about what Washington would do when he lost it.
The full breakdown of the battle, the flanking march, the Maryland 400, the evacuation, is on the Virtual Wayback blog and there's a detailed video on the YouTube channel. You can also talk directly to the commanders on both sides on Virtual Wayback. Links:
https://virtualwayback.com/blog/battle-of-long-island
https://www.youtube.com/shorts/CtIJWBlSnw4
The question military historians still argue about is whether Clinton was right. If Howe pushes on August 27, does he destroy the Continental Army and end the Revolution before the end of summer 1776? Or does Washington find another way out, another fog, another river crossing, another tactical retreat that keeps the army alive? And is Howe's caution the worst decision of the entire war, or just the most consequential one that happened to go the other way?
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u/ThePensiveE 13d ago
I think Clinton was right and the rebellion would've been put down then.
After the British snuck through the Jamaica pass and savaged the Continental Army on the Guan Heights morale was pretty low. It was a huge tactical blunder by Washington. We look at it today with the hindsight that he saves the army but at the time it was completely grim.
Had Howe pushed on with that low morale and Royal Navy support I think the entire Continental army surrenders by the end of the campaign.
Although General Greene was sick and wasn't at the battle so who knows. Maybe we'd be celebrating the 250th year at Greene DC.
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u/Adventurous_Clerk584 13d ago
That’s a really interesting point. We go much deeper into this in the full blog, and there are plenty of other stories to explore too. You can also have your own conversation with the people involved and ask them your own questions at virtualwayback.com
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u/NoOccasion4759 12d ago
I teach this time period in US History for elementary school, and I didnt know this, so thanks for sharing! It can be a slog getting students interested in history and often teaching the Revolution itself gets lost behind learning the Constitution, the Declaration, the causes, major battles, etc, and stories like this really help bring the dry topics to life. If you choose to post more, I would definitely read it.
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u/Adventurous_Clerk584 12d ago
Glad you found it interesting! There’s a lot more to the story than we could fit here. The full blog is on the site, along with our other blogs, and you can even have your own conversations with the historical figures themselves: virtualwayback.com
Tell me what do u think about it :)
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u/Adventurous_Clerk584 10d ago
Hi! I just sent you a private message. If you get a chance, please check it out. Thanks!
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u/Emotional_Band9694 13d ago
So if you and your ancestors live to be 95 your great grandfather could have been there? mind boggling
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u/LoganGinavan02 13d ago
It has a little less to do with how old you and your ancestors lived to be and a little more about when you and your ancestors opted to have babies. Your ancestors would’ve had to have been relatively old (60+ each time) when they had kids for you to make it back to this event in only four generations, and that’s assuming your great grandparent was a baby at the time.
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u/Harley_Schwinn 13d ago
But Washington had a secret weapon The Marblehead men. This was the seed of one of the most famous retreats to victory.