What's the earliest the US can win a war of secession?

It seems to be conventional wisdom around here that a Civil War even ten years earlier is likely to go in favor of the *CSA, but how ironclad is this?

This is in relation to my Shared Worlds Game, where the US has so far elected

1. George Washington
2. John Jay
3. Levi Lincoln
4. John Quincy Adams

Never mind how plausible that is, if the US keeps electing northern liberals, at what point does the South break off, and what are the odds that an earlier secession will stick? How much does Virginia's choice affect the outcome?
 
Pretty early. 1850+ sees the balance wildly in "the North's" favor, but even earlier on still sees the national government having well, the national government - the regular army (and most of its officers), the navy, the areas that developed industry fastest . . .
 
1848 with the conclusion of the Mexican-American war. Before this it would probably be a fairly even match, but with industrialization moving quickly and railways developing across the northern US it becomes ever more difficult for the South to leave.
 
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