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WI: Pro-Slavery Forces Victorious in Kansas

I came up with this thought when learning that the state allowed segregation after emancipation, but what if William Quantrill and the pro-slavery forces emerged victorious in Kansas during the skirmish infamously known as "Bleeding Kansas"? Obviously KS would be admitted to the union as a pro-slavery state. When the American Civil War would come around, do you think a pro-slavery KS would secede or remain in the Union as a Border State?


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Your odds of that happening are between slim and none. The Lecompton Constitution, which permitted slavery, was promulgated because 10,000 Missouri border ruffians came to Kansas and voted even though they were citizens from another state. The anti-slavery forces in the state were very strong. Remember, this is the state where John Brown goes from being a failed tanner to the terror of Pottawatomie Creek. The best result that could be hoped for would be that Kansas becomes a Kentucky or a Missouri, neutral one way or another. Maybe you get 5 or 6 regiments of infantry or cavalry serving with the Confederacy, no more than that.
At the time of the Lecompton Constitution, the free-staters had already won control of the territorial legislature. They could not abolish slavery in Kansas--one of the tricks in the Lecompton Constitution was to forbid its being amended for several years--but I doubt that many slaveholders would want to come to a state with a hostile legislature.
Not happening unless something big changes. Pro-slavery settlers were vastly outnumbered by Free-State settlers. The only reason the Lecompton Constitution happened at all was because of extreme voter fraud when people literally crossed the border from slave state Missouri to cast a vote for slavery, then headed back once they had cast their ballots. It was so blatant that even Stephen Douglas turned against it when it came up for approval by Congress. The only way Kansas becomes a slave state is if there is increased immigration from Southern states such that they have the numbers. Otherwise, it was never going to happen.
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Kansas wasn't good for slavery anyways. The farms being bought up were too small and there were too many people who wanted them for slavery to have too much structural success. Not to mention the demographics of who was coming in. The majority were clearly northerners not amenable to slavery, particularly New Englanders.

For the pro-Slavery forces to have success, you will need to drastically alter the proportion of northerners to southerners coming into the territory, and have Missourians wage a more severe and longlasting campaign of terror to drive out the abolitionists.

Of course, even if Kansas does become a slave territory, it will be blocked from admission to the US, or would be admitted alongside Minnesota to keep the balance, pushing back Minnesota's statehood. And it will, if it secedes, find itself under military occupation by spring 1862 at the latest.