The questions you raise are too broad, and too important, to be addressed in a letter. As to what I think is going on -- pretty much what has been going on in the past. I've outlined what I think in recent publications, for example, in a chapter of a book "Year 501" published last year. I also try to show there (and elsewhere) that US policies towards Cuba are part of a far more general pattern, quite intelligible in terms of domestic power structures, and amply illustrated in the historical and documentary record, though quite inconsistent with the fairy tales that are preferred by the commissar class (to use an unkind but generally accurate term).
Very briefly, since the 1820s Cuba has been regarded by US elites as basically theirs, though they couldn't grasp the "ripe fruit" (as they put it then) until the British deterrent was removed. When it was, the US took the country over and turned it into a US plantation. No departure from obedience was tolerable. FDR's "good neighbor policy," for example, was shelved rapidly when it became necessary to reverse a deviation that threatened to allow some degree of independence and democracy. Within months of the success of the Castro revolution, Cuba was being bombed from US territory, and by March 1960 the US had secretly determined to overthrow the regime. This had nothing to do with Russia, Communism, dictatorship,... -- rather, with independence. There followed direct aggression, a huge terror campaign of unprecedented scale, economic warfare, and in fact, every possible means to get rid of this "rotten apple." Cuba was considered particularly dangerous because it sank so low as to direct resources to the benefit of the poor majority and, even worse, to support popular movements elsewhere that sought freedom from US-imposed or -backed monsters of one or another variety (what is called "subversion" or "aggression"). Another major crime was Cuba's contributions to health and welfare in poor and suffering countries, absolutely without precedent, and considered extremely dangerous, particularly in the light of the sordid record of those who have the wealth to confront and overcome those problems were they not to choose to exacerbate them -- us, in particular.
For decades, the pretext for the terror and economic warfare was that Cuba was an outpost of the evil empire, threatening our security. When the evil empire collapsed, that excuse was quickly shelved, as useless, and forgotten, and the noose was tightened, again by the Bush administration (under pressure from liberal Democrats and the Clinton campaign), now again. These policies have long been in defiance of such trivialities as international law, world opinion (votes in the UN, including our allies), etc. In brief, a continuation of what has been going on for 170 years, and a particularly clear instance of far more general patterns, invisible only to those who make a real effort not to see.
As for the regime, it's a dictatorship, often brutal though a teddy bear in comparison with numerous US friends and clients, with plenty of human rights violations, etc. The US hopes to increase these as much as possible, for obvious reasons: (1) that will increase internal disorder, and (2) it is ideologically useful as a weapon against the hated enemy. But it is trivial to demonstrate that Cuba's crimes, however you evaluate them, are irrelevant to US policy; the US happily supports and conducts itself far worse crimes, including its crimes against Cuba. Since the Russian collapse, the idea has been to tighten the stranglehold so as to impose maximal suffering and oppression, hence increased resistance and more repression and suffering, in the hope that sooner or later people will be desperate enough to welcome the Marines. Even loyal apologists generally concede what is obvious enough from the reporting that comes through: people are trying to get out because they are suffering from the collapsing economy. Naturally, no small country in the US sphere can survive such an attack by the superpower hegemon without extensive outside support, and there are few willing to brave the anger of the world's leading Mafia don.
A crucial requirement is that articulate opinion in the US efface completely what is happening before our eyes, however obvious it is, even (at the most extreme levels of servility, regularly attained) to portray us as victims of Castro -- standard in mainstream commentary. That this requirement will be amply fulfilled is scarcely in doubt, so policy can continue on course.
How should honest people react? First, with utter revulsion. Second, by doing what they can to allow Cubans to deal with their problems themselves, without our domination and control -- which, as history amply shows, will cause them endless pain and torture. Personally, I'd like to see the regime overthrown by an internal libertarian revolution (and not that one alone). But I don't expect the US to implement such initiatives any more than it does in the vast areas of the world in which it has enormous influence, including at home -- and if the US were to change so radically that that were a possibility, or if there were some other entity in the global system so noble that such possibilities could be contemplated without ridicule, I wouldn't want them to intervene either, nor would they choose to, if they had actually achieved this (unimaginable) level of honor. The reasons are those that have been familiar for centuries, articulated by Kant and other Enlightenment figures for example: freedom can only be won, not granted by a benevolent power. Those who are fighting for freedom can sometimes be helped, but only by those committed to freedom, that is, those who oppose terror, oppression, injustice, and domination honestly, beginning with the societies of which they are part (where they will find plenty).
At this level of extreme generality, anything said is bound to be inadequate and misleading, but a really serious effort to deal with the issues would overwhelm this medium, I think.
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