The Cuban version of "Survivor" is the only one where the person NOT voted off the island loses.
Our Cuban policy has kept Castro in power. Unlike Eastern Europe, Cuba is far away from the Soviet Union. So unlike the Eastern communists, he was not kept in power with the threat of Soviet invasion. Rather, he kept himself in power by beggaring his nation. By making people turn their thoughts away from liberty and towards bare survival, he protected the regime. (Cuba in 1959 was not a poverty stricken island -- it was actually fairly prosperous. The Cuban Revolution was driven largely by the fact that the Cuban middle class was tired of playing Batista's tune).
The embargo made Castro's job easier and gave him an excuse for everything.
On top of that, the closeness of the US gave him an escape value. So people who wanted a better life for themselves jumped into inner tubes and headed north.
I am not sure where to go next. Obviously, in an election year, not much will happen. But going forward, progress can be made. Raul Castro needs to be given a face saving out. At the very least, he needs to be rewarded if he releases some political prisoners and loosens restrictions on the media. A full blown liberal democracy may take some more time, but maybe not all that much. With the exception of Haiti, pretty much all of Latin America is democratic these days. Granted, Venezuela is heading in the opposite direction, but it is Cuba which is bucking the regional and cultural trends.
Well, to Cuba Libre!