I think this is a naive perspective, historically speaking. For starters, Cuba was a dictatorship already before Castro rose to power, but Batista was backed by

I think this is a naive perspective, historically speaking. For starters, Cuba was a dictatorship already before Castro rose to power, but Batista was backed by the US. Around the same time, Chile's Pinochet overthrew the democratically elected socialist government with CIA's aid. Currently, the US backs a handful of dictatorships, of which some are former democracies. Egypt may be an example of former democracy, albeit flawed, turned into a military dictatorship. And among de facto dictatorships that the US still maintain perfectly open relationships are Thailand, Myanmar, and Morocco.