Jd Smith1
Hero
Brown was attacking in the wrong places.
Instead of having a whole mess of men in one place shooting people what he should have done was sent them around to different towns and then had them all sneak out and torch the local cotton fields on a predetermined day (the coordination of the times would be circumvent the widespread security increases that would no doubt come about if they set the fires one at a time)
EDIT:
More to the point the Union accomplished the same thing Brown was trying to using similar tactics to Brown. Now, this isn't particularly relevant to discussions of the real civil war since brown only had a few guys, but in a fantasy setting like we're discussing a few guys could be equal to the army of a large nation.
There has been exactly one successful slave revolt in history, and the only reason it succeeded was because local diseases crippled the troops, and the owning power had bigger problems.
You don't burn cotton in the field, you burn it after it is gathered and baled. All that would have accomplished is to further discredit the abolitionist movement. They had already suffered because of Bloody Kansas, and if Brown, a nutjob, had embarked on a program of destroying private property, it would have tarred the abolitionist movement with the same brush. As Celebrim noted, slavery was not a huge issue in the north, and Brown's historical nonsense only hurt the movement.
The key to slavery is that it is an economic institution. Slaves in the USA were expensive, and many large plantation owners had to take out loans to purchase them. The abolitionist movement make a very smart move when they got the importation of slaves banned (Jim Bowie got his start smuggling slaves in, on a side note); but they they made a very stupid one when they pushed for rendering slavery illegal, because would strip away a vast amount of capitol investment.
The smart move would have been to campaign to render slavery illegal, while providing the (now former) owners of slaves with compensation for the loss of their investments; some sort of tax deferment possibly. The British used a similar system with considerable success.
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