The embargo on Cuba is unbelievably silly in 2026:

- The Cold War is over and Cuba poses no security risk - Florida is no longer a swing state and appeasing Cuban Americans is not a worthwhile political move - We are willing to ally with much more oppressive regimes for less geopolitical benefits - Cuba was in the process of liberalizing and developing an independent middle class for the first time in half a century before Trump's last crackdown.

The jury is out on whether the "regime change" (or more like, junior dictator promotion) in Venezuela was worthwhile. It's certainly looking like a quagmire in Iran.

By hardballing GAESA, we're probably shooting ourselves in the foot by making the Cuban population more resentful of the US. "Regime change" is a less likely positive outcome than it was 8 years ago.

But we have plenty of models of military dictatorships slowly opening up to becoming stable economies through trade and access. More or less that's what happened with Vietnam, to name one.

My impression is that while the final outcome is yet to be seen, Syria's current administration is a decent example of a government that one would naively expect to be fairly regressive recognizing the power and prosperity granted by liberalization.