There is a very good article in last Foreign Affairs about the failure of US foreign policy in Cuba, and the way ahead. It makes a comparison between failed US efforts at de-Baathification in Iraq, and any similar attempt at de-Fidelista purges that the US may wish to see post-Fidel. If this were to happen in Cuba, you would essentially be eliminating the entire white-collar work force of the country. It also points out the extraordinary influence ex-pats or ex-pat communities can have on the US government. While Ahmed Chalabi springs to mind, he fails in comparison with the influence the 1.5 million cuban ex-pat community has on federal policy.
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