No big deal. World leader's often have to work with or at least get along with other heads of state that may be a bit unsavory. FDR met with Stalin which was probably necessary, though he should have stood up to Stalin more. Also I think Raul Castro has been making some reforms towards a more free country, I remember hearing a few years ago that he let people legally own cellphones, plus the Cuban government has been in negotiations with Spain and the Archbishop of Havana that have gotten some political prisoners released, though there are still some prisoners I think. For his part, Fidel Castor did reinstate Christmas as a national holiday (he had suppressed it after taking power, but he reinstated it as a token of gratitude to Pope John Paul II for speaking out against the embargo). That being said I think Obama could've used that handshake as an opportunity to talk to Castro about Alan Grossman who is an American citizen imprisoned in Cuba (maybe he did, I don't know). I think the U.S. should end or begin to loosen its embargo and travel restrictions on Cuba, and that the communist regime in Cuba will probably lose power eventually (I mean the Castro brothers are up there in age).
I think the bigger deal with Obama is the deal that the U.S. and Iran entered into. Among other things the U.S. released an Iranian nuclear scientist, but the Iranians still have Saeed Abedini, who is a dual American-Iranian citizen imprisoned because of his religion, in prison.
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