A distinction: not "with-such-a-neighbour-how-could-he-do-different" but rather "with-such-a-neighbour-it's-not-too-surprising-he-didn't-do-better".

I'm sure it would have been possible to avoid a lot of the follies and worse-than-follies that have taken place in Cuba over the Castro years. In the same way it would have been possible for the United States to avoid its own follies and worse-than-follies.

And in regard to Cuba these have consistently been such as to push the regime there in the direction that undermined any hope of liberalisation and reform. Because that is not what is wanted by the people who have shaped US policies.