Slate has a article yesterday on the Bush Administration's policy on Cuba. His policy is nothing new, hell its really Eisenhower's policy. When are we going to learn that embargoes do not work? 45 years of failed policy should teach you that. We have apparently decided that we are going to go this course until Castro dies. Then what?
Castro has not groomed a successor. It is widely viewed that Castro's younger brother Raul, would take control of Cuba upon Fidel's demise. Raul, however, isn't thought to be able to do the job for long. He's 72, and in poor health. So, soon after Fidel's death there is probably going to military junta. So, what are our options when this happens?
One other option is military intervention. Global Security estimates that would take 60,000 troops to pull this off. We don't have them right now, anyway. The Cuban military is the only stabilizing force in Cuba right now. So, an invasion would cause another Iraq type fuck up. Probably even worse as heavily armed exiles would return to forcibly attempt to reclaim their land.
Another option would be to provide air cover for pro democracy forces and let them try to take over. They would be slaughtered, though, and we would be right back where we started from.
I think the way for the US to go in the event of Fidels death would be to let the Cuban military sort it out, then engage the new government. This would be political suicide with 1st generation Cuban exiles, but with Florida going so decidedly red in the last election, this group shouldn't be able to exact as much power on Cuban foreign policy as in the past. Also, if you look at the regimes around the world that have had surges in democracy in the near past has all been in countries with western economic influence. Iraq doesn't count, by the way, while it is true we are dumping a ton of money in there, it doesn't help when you're also killing off their people.