How can there be an American victory at Long Island

In OTL the battle of Long Island was a major defeat mostly due to superior British tactics and the failure of the Continental Army to defend Jamaica Pass. But what would have led the Americans to win? Would it have been Greene not getting sick or Jamaica Road being defended?
 
Generals Howe and Clinton are fired along with General Gage following Bunker Hill and the loss of Boston. They are replaced by an incompetent political appointee General X who dismisses any possibility of the Colonials representing any threat, and invades New York City with a fraction of the forces used IOTL.
 
The best-case scenario for the Continental Army would be to delay the British and inflict signficant casualties before retreating. Given the military technology of the time, New York was indefensible against an attacker with naval supremecy, since any position could be outflanked by a naval landing.

IOTL, both sides initially overestimated the effectiveness of American shore batteries. This is why the Americans attempted to defend forward positions and the British obliged by attacking them rather than just landing upstream, until British probing attacks demonstrated later in the New York campaign demonstrated that they could easily run past the guns.

If the Americans put up a better show at Long Island, the British would have risked running the guns earlier, then simply bypassed the defenses and landed in Manhattan.
 

Redhand

Banned
The best-case scenario for the Continental Army would be to delay the British and inflict signficant casualties before retreating. Given the military technology of the time, New York was indefensible against an attacker with naval supremecy, since any position could be outflanked by a naval landing.

IOTL, both sides initially overestimated the effectiveness of American shore batteries. This is why the Americans attempted to defend forward positions and the British obliged by attacking them rather than just landing upstream, until British probing attacks demonstrated later in the New York campaign demonstrated that they could easily run past the guns.

If the Americans put up a better show at Long Island, the British would have risked running the guns earlier, then simply bypassed the defenses and landed in Manhattan.

The shore batteries were fine until the disaster at Kips Bay, in which the shore batteries under Knox accounted for themselves quite well in turning back the navy on the Hudson while army fell apart on the East River. When the Americans held Governors Island, the batteries really were quite a nuisance. The retreat from New York City led to a lot of cannons and more importantly ammunition being abandoned as the entire garrison of the city under Putnam fled to avoid being cut off. Later on in the campaign, the successes you referenced came from the American units being at the poit of disintegration both logistically and in terms of manpower.
 

Redhand

Banned
In OTL the battle of Long Island was a major defeat mostly due to superior British tactics and the failure of the Continental Army to defend Jamaica Pass. But what would have led the Americans to win? Would it have been Greene not getting sick or Jamaica Road being defended?

Greene would have helped, but the truth was that even had Howe attacked straight on and not found the flank, he still would have won. The American forces facing them were outnumbered 3 to 1 and of the troops present, most had not seen combat and nearly half of them were completely untrained and were likely armed with scythes or fowling pieces. It wasnt a fair fight.

Conceding Long Island was probably a good idea but then again so would conceding and burning New York, neither of which were politically feasible.

Possibly building an extensive trench network on the Gowanus Heights along with putting up a ton of obstacles on Long Island months in advance (caltrops, ditches, felled trees) and having the British not march on Jamaica Pass, along with having for once ammunition in abundance might lead to a chance at victory.
 
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