The Obama administration’s decision to begin normalizing relations with Cuba has generated much praise and criticism. You can read the lead editorials in the New York Times and the Washington Post to get a flavor for the arguments, pro and con. On the right, the divisions between conservatives and libertarians have found a predictable expression. The editors of National Review are not happy. They conclude: “We fear that yesterday was a good day for the Castros and a bad day for the Cuban people, and for American foreign policy.” In contrast, Juan Carlos Hidalgo (Cato) strikes a much different tone: “The president’s move should be uncontroversial. U.S. policy toward Cuba has been a blatant failure. It has not brought about democracy to the island and instead provided Havana with an excuse to portray itself as the victim of U.S. aggression. It has also served as the scapegoat for the dilapidated state of Cuba’s economy.”
There is little to praise in Cuba. It remains a dictatorship. On the World Freedom Index, it ranks 170. But China ranks 175 and is a far greater concern with respect to national security. Last year our exports to China were $121.7 billion and our imports from China were $440.5 billion. While progress has been slower in China than many would have hoped, there is much evidence that trade has positive implications with respect to property rights and political liberalization. Perhaps this will be the case in Cuba.
Even if one assumes for the sake of argument that the US policy toward Cuba made sense in the early 1960s, it is difficult to see precisely what justification one can find decades after the end of the Cold War and the dissolution of the Soviet Union. Beyond the antiquated assumptions upon which the policy rests, there is little to suggest that our approach has been effective and much to suggest that it has been both counterproductive and costly.
Of course, in this there is little to separate our Cuba policy from so many other policies that remain firmly in place (e.g., agricultural subsidies, corporate welfare, the punitive war on drugs). Alas, there remains much work to be done.
PILEUS 
My objections to this development have more to do with the rhetoric than with the policy per se. As he frequently does the President uses language that confuses more than it clarifies. Historically diplomatic relations have been with governments of states that we recognize. Obama would have us believe that this is about relationships of peoples, in this case American and Cubans. This will be but a very small part of the deal and it is simply misleading to speak of diplomatic ties as ties between peoples. So the real issue is that the government gains in all of this and what the Castro regime gains.