Our limited relations with Cuba during the Cold War, in which we isolated a hostile Soviet client state, made perfect sense. With the end of that conflict, this policy became increasingly anachronistic, although it was still useful as Cuba supported disruptive elements around the world. At this point, however, while being fully aware that Cuba still has an oppressive government, it makes sense to reconnect with Cuba. We can do far more good with normal relations, allowing the Cuban people to stop seeing us as enemies, to learn the value of American democracy and capitalism and to, eventually, get rid of the Castro regime (hopefully, through peaceful means).
When a policy - in this case, decades of isolation - fails to have a meaningful effect and the original reason for it - to constrain a client of a hostile power - is gone, it is time to re-examine that policy. And, for those who say we shouldn't have relations with authoritarian states that abuse human rights, I assume you are willing to carry that line of reasoning to its logical conclusion and advocate for cutting ties with countries that have worse records, like China and Russia.
You can have relations with adversaries. We have done this in the past, we do it now, and we will do so in the future. You can have relations with states that do not uphold your values. You do these things for a variety of reasons. They may have resources we need (e.g., oil). They may have a useful geostrategic position (e.g., supporting South Korea before it became a democracy). You might do it just so that you can talk to an adversary, to keep tensions from boiling over (e.g., having diplomatic relations, cultural exchanges and trade with the USSR). And, you can do it because those ties can lead to social and political change in the adversarial state.
More details still need to be released about exactly what the new relationship will be like. We'll have to see how the White House deals with the legal restrictions in place. They should work with the new Congress to get the controlling laws changed, not act by fiat. We also need to be watchful of how the Cuban government responds to steps on our part to open up, adopting a policy of relaxing sanctions in a staged fashion. If they respond by addressing human rights abuses and truly opening up the political process - creating a true democracy - then we can continue to remove sanctions, until we have fully normal relations with them. This should only happen at the end of a process, in which we are satisfied that Cuba can become a democratic partner.
Sources: CNN, Statement of the President
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