Political freedoms come with a cost. For example, Iran had democratic political freedoms, and then the US and UK exploited those freedoms to launch a coup and rob the country. So when the Iranians finally likes them out again, they did so with the awareness that they couldn't just do another liberal democracy with political freedom, they actually had to clamp down in order to prevent losing their country again.

Cuba is in the same predicament. Political freedom when you're under a siege is very very difficult. The number of times the US tried to assassinate Cuban leaders alone is the reason for tighter political controls, but the US has also spent billions of dollars on propaganda and covert ops to overthrow Cuba and return it to the control of American organized crime. And it's even worse than the Iran situation because the US literally has a covert ops military torture prison on Cuba from which to launch, coordinate, and monitor any campaign of any type.

You wouldn't expect a city under medieval siege to have broad political freedoms, why would we expect weaker nations founded on anti-imperialism to have broad political freedoms when under active siege by the most psychotic beligerents in the world?