The issues are complex.
Castro lived in the shadow of US aggression for 50 years.
But in summary, not in all cases does freedom of speech, free elections,'free market' etc favor national stability.
Singapore did very well under Lee kwan Yew in what was essentially a one party state. So did Libya so is modern Rwanda. Not every country will blossom under western democratic prescriptions. A friend of mine whom I had a conversation with a few years ago, pointed out that universal suffrage and free elections if adopted in China would be the fastest way to destroy the country.