WI The British win the war of 1812

A slightly more clear result than the historical one seems to be the most likely outcome featuring a real British victory. Occupying all the rather extensive territory you mention seems rather difficult. I would also take into account the chance that those colonial upstarts will be smarting for a rematch, maybe pretty soon, intended to take all of that back.



The problem was the same as in the 1775 war, US was too primitive, power too distributed, there is no central important place, no vital center.
 
The most you could probably ask for is Britain accepting Maine into Canada as part of the peace treaty if the people of Maine asked for it. That's even a stretch I think because it seems pretty unlikely barring some outstanding circumstances, but it could happen.

The simple truth is that the Americans just didn't warrant the attention Napoleon did, and that's why the British were never so interested in a) extorting them for territory or b) prosecuting the war more vigorously.
 
The British did win the war of 1812. The only reason that it's remembered as a draw is the Battle of New Orleans which took place after the peace. The British repelled the US assault on Canada, burned DC to the ground and despite some small but embarrassing defeats at sea, ruled there as well.

The British war goal was basically to put the Americans in their place. They didn't particularly want to fight the Americans at all and the best British generals turned down the position in both the Revolution and War of 1812. A peace in which England attempted to block US expansion west would only lead to another war a few years down the road and by then the US would be much much stronger. The British weren't fools, they won the war and then gave the US nearly everything they'd asked for since it really didn't cost England much at all and would help keep the peace for years. Even if they had much more success I doubt Britain would have demanded territorial concessions.

But as I have repeatedly explained, they *did* so demand in August 1814 when they thought they were winning. https://www.alternatehistory.com/discussion/showpost.php?p=8573584
 
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