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It's not really material how this happens. Suffice to say that in the War of 1812 the U.S. manages to fluke itself way into victory. Perhaps Napoleon does better in Russia forcing the British to focus more and longer on Europe. It doesn't really matter.

However, having won it's simply not as easy as annexing the Mexican cession. Unlike the prewar predictions the Canadians did not welcome the Americans as liberators. They fought them wholeheartedly. The Maritimes and Upper Canada are inhabited by white anglo-saxon protestants. They simply can not be oppressed, disposed of their land, etc like the Mexicans and Native Americans. The political culture of the United States at this time can not bear this. The expulsion of loyalists after the revolution is simply not comparable. For one thing there is no significant class of elites to favor in opposition to the loyalists, they were all loyalists in Canada. Secondly the American political climate had changed since that time. There is not the personal enmity that was characterized by decades of political and open warfare that engendered the reprisals against the loyalists after the Revolution. The New England states which were lukewarm on the war in the first won't support harsh measures that are likely to disrupt trade and I don't think the South could possibly have the stomach for such a widespread usurpation of private property of a white upper class, it sets a very bad precedent. Nor can they be occupied by a standing army for more than a decade after the war like the south after reconstruction, a standing army of such size and power was politically anathema to America at the time, so much so that they went to war with one of the two strongest nations in the world with virtually nothing but state militia.

Simply put the Maritimes and Upper Canada must be given statehood if they come under U.S. rule, and the states having much more sovereign power at that time, what is to stop them from jumping ship and seceding at the first opportunity. How could they be trusted not to conspire with foreign powers, particularly Great Britain? It is a Civil War waiting to happen.

I don't see how these problems could be overcome and the people in charge would understand that. If the US somehow won in 1812 they would at most demand the cession of the Oregon Country and Rupert's Land.
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