Sometimes counter factual reasoning from history can be interesting and possibly even interesting. For example, I find it interesting to think about what changes could have resulted in leaders in South Carolina or Virginia to have chosen to support the Union rather than secede.
On the other hand, it seems to me that the farther from historical fact that one strays, the more dangerous counter factual reasoning becomes. To continue the Civil War example, the Confederacy was crushed; it lost the war in a big way. Trying to figure out how it might have succeeded in secession seems to me to be intellectually perilous.
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