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In the OTL battle of Long Island, General George Washington dug in at Brooklyn Heights to act as a last line of defense. The Continental Army and the militia got defeated on August 27th and retreated to Brooklyn Heights. The Patriots tried to decide between digging in further or retreating and eventually settled on retreating. On the night of August 29th, the Patriots retreated, taking with them almost everything. They took every man, almost all of their supplies, and most of their artillery. Actually the night didn't give them enough time, but a fog obscured the retreat in the morning of August 30th for the last few hours they needed.

Suppose that the Patriots did not get away so smoothly. The British were digging their way towards the American position and expected the Renaissance Era trench warfare these sieges offered.

Suppose in TTL, Howe authorizes his junior officers to make night raids as they deem fit, but reminds them they are on the hook for any that goes badly. The British still do not expect a retreat so there is no sense to urgently make a full assault to take the Americans.

At 3 AM August 30th, some of the British officers have units make probing attempts and find some areas where the defenses seem sparsely manned. Night raiders are sent, in the same style that they did in OTL Siege of Gibraltar. General Washington was with the Rearguard trying to keep morale up when fighting breaks out in his section. He is shot three times in the left leg, many Redcoats overrun his area in a bayonet charge, and Washington is knocked prone in hand to hang combat. In the darkness, they mistake him for unconscious and don't recognize him as the commander. Thomas Mifflin has other rearguard units drive out the raiders in this section and Washington is rescued. He is evacuated unconscious.

The problem is every time the American rearguard shifts, more British majors keep noticing opportunities in the thinning American line. Light infantry is awaken from their camps and told to be on standby, and every time weakness is sensed another raiding party is sent.

Eventually Howe is awakened and told that the Americans seem to be in disarray. Eventually he orders his cavalry into a place where another raiding party had already engaged the Americans. The American line was thinned by men retreating and by combat, and in many places night raiders had already gotten into the camp. Whole units start to rout, but are trapped by the sea.

In the aftermath, the result is the destruction of the rearguard and Thomas Mifflin later dies of infected wounds. The British lost 75 dead and 25 wounded. The Americans suffer 234 dead, 50 wounded, and 2940 captured. Almost all the horse artillery (evacuated in OTL) is captured, as well as the 5 heavy cannons (got stuck in the mud in OTL, same here probably). Instead of their entire supply train, the retreating army has 7 days worth of rations.

The casualty breakdown of the American side is 750 of the Continental Army, 1,370 of the new York Militia, 340 of the New Jersey Militia, and 764 of the Massachusetts Militia.

Oh those casualty breakdown are for the rearguard action at Brooklyn heights, not the whole battle. The OTL battle of the 27th happens in TTL.

General Washington recovers from his founds and he does not get a nasty infection. He's walking around in a week and there are tales of how he bravely fought the raids alongside his men. The majority of the army that was left after the August 27th battle managed to get away. On the other hand, they left more than 3,000 of their own behind as dead or captured.

What do you think the developments in the war might be. In OTL General Howe's plan after taking New York seemed to be just grabbing the small villages and hamlets in New Jersey and Pennsylvania and protecting Loyalists so they feel safe, winning over the population and restoring stability. After the reverse at Princeton, he changed his mind, decided his forces were too spread out, and concentrated them into a field army to take Philadelphia. Would Howe just continue his original plan in TTL?
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