I think Obama needs to understand that some of these nations will not change unless their "dear leaders" die. Cuba is a case in point.
The Cuban president suggested the communist government is not willing to appease Washington by embracing small political and social reforms on the island, saying in a speech before an international gathering of government ministers that "it is not Cuba who has to make gestures."
The Castros are in their 80s so it will just be a few more years until they are dead. After that Cuba will probably be a free and democratic society. I call this the "one-man roadblock to peace" principal. You had this with Stalin, Yasser Arafat, and Kim Jong Il. You might have had this with Saddam too if we didn't remove him from power.
These roadblocks are usually old men with shaky heirs that they probably can't entrust their country to. They want to hold on to power and not be marginalized after terrorizing their country for decades. They won't change their ways because there is absolutely nothing in it for them. They already have the billions stolen from the countries treasuries. Why release political prisoners and change to a democratic system when you had the power of life and death over their subjects for years?
However, once they die then new possibilities are opened up almost immediately. Stalin's body wasn't even cold when Russia started instituting reforms. I can see us lifting the embargo the day after both Castros are put into the ground. Until then any US overture is a big waste of time. Sometimes change can only come over the body of a dictator.
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