Blackwater might be strong enough to take over Cuba and hold it. Especially if they didn't care about the Geneva Convention or human rights. Never underestimate what people will do for the right amount of money. But they wouldn't fight against the US military. They know better than that. And I'm sure there would be enough support of the democratic process in the military to recognize the new commander in chief as elected by the states.
If you've ever seen the TV show Jericho, something like that would have to happen for Bush to stay in power past Jan 20. And even then, unless the President-elect died in a major attack or biological outbreak, they would want to take over anyways.
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