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General Henry Clinton receives the news of the surrender of the British Army under Cornwallis at Yorktown. Realizing that the loss of that army will have an extremely negative impact on the British government and public likely breaking their will to continue the war he decides to make one last desperate throw of the dice. He realizes that to lay siege to Cornwallis General Washington has taken the bulk of the Northern Continental Army south to Yorktown and the French Forces under Rochambeau has traveled south with him. Realizing that the Highlands are severely undermanned he is going to strike north against West Point. Other than Arnold's treachery this was the one moment when the British had the best chance of success against the fortifications at West Point.

Washington left the the bulk of the Massachusetts line in the Hudson Highlands minus their light infantry companies that he took to Yorktown. The Massachusetts Line is one of the best equipped and well motivated of the various state lines but they were never as tested as say the Maryland or Delaware Lines. All total you have about 2,500 to 3,000 Continental troops in the Highlands plus state troops and militia. Clinton has 17,000 troops in NYC but he has to maintain his hold on NYC and leave enough troops to block any counterattack that the Washington will launch as he attempts to race his army back north to protect the Highlands. Assume that General Heath receives news of Clinton's intent and has time to move his troops into the fortifications at West Point and call for additional troops from the states and militia.

1) So can Clinton take West Point and control of the Hudson?

2) How murderous will his causalities be? Is there the potential that they might be so great that it would leave the British in a worse position at home then they were historically after the loss of Cornwallis Army?

3) Does taking and controlling West Point and the Hudson achieve enough for the British?

4) Can they hold it against the combined American and French force returning from Yorktown and also maintain control of NYC?

The trouble with this is British at Yorktown surrendered in late October 1781 and word of this would not have reached New York until the end of the month at the earliest. So an operation against West Point could not get underway before into November and that does not leave any time to mount a major campaign before winter sets in. Winter conditions could make the use of black powder arms almost impossible and would place a severe burden on moving British troops who had no prepared shelters. Disease and exposure killed several men for every one lost to a bullet back then. Clinton would not risk such an operation, which if it went poorly enough could turn the loss at Yorktown in the complete collapse of British forces in the thirteen colonies and could result in an all out invasion of Canada.

Now if he did go attack, and the snow held off, the forts at West Point were nothing very strong, and had not been well maintained, nor ever well garrisoned. They might fall to a strong assault after a fairly short siege. But its also easy to see losing a thousand men on the campaign or twice that even if the winter is bad enough, and another two thousand would be the minimal required for an acceptable garrison for an isolated set of mutually supporting forts. That’s not good; IIRC the British only had about 18,000 men in New York City. Take away 3,000 and that leaves 15,000, while the combined American-French Army at Yorktown was about 20,000 men strong and overwhelmed 7,000 British. When it comes back north it can grow even stronger and the British can't know if the French will send more troops or not. So this is certainly creating a serious risk to New York, and it would just not be possible to hold West Point against a spring or summer counter attack. So all the British gain is holding the Hudson for a winter. No doubt this is why it didn't happen.

The British needed another complete army 15-20,000 men strong sent to the colonies to accomplish anything more after Yorktown. No one back home wanted to pay for it, nor could the manpower be quickly mustered. All I see in this operation is potential for British losses, and gaining possession of West Point has no political and precious little economic or military value. Its certainly does court disaster, though I think one is unlikely.