You specifically referred to "states where the US implemented the control measures of a long containment strategy that has nurtured the rise of the majority of the states that top the "least free" list". That is demonstrably not true.
I won't take the time to break down the 47 but on a quick scan it does not at all seem to be dominated by US allies or regimes the US nurtured as part of a strategy of containment. I suspect that on a global basis you'd find that more of those "US-nurtured" despotisms have made the transition to democracy than those of the many despots we didn't nurture.
Who exactly is showing up to "help the populace gain freedom"?
We should not be so naive as to think that anyone who fights a despot is fighting for freedom. Often they've simply spotted a weak regime that they think they can replace with their own despotism. Often the populace is quite aware of this: why do you think the populaces of Saudi Arabia and the Gulf States have shown so little interest in AQ's attempts to lead them into a new form of despotism? I doubt that it's because they love their rulers: they just see that AQ has nothing better to offer.
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