You’re assuming Obama wants regime change in Cuba, which I highly doubt.
In 1939, Henry Stimson took his annual trip through the Eastern Establishment recruiting people for government service. In those days, one worked in the private sector first, then in government service, which is exactly the opposite of how it is done today. In that year he recruited the 31 year old Nelson Rockefeller to take over the Latin American desk at the State Department. Because of his family’s oil holdings in Venezuela, Rockefeller spoke Spanish like a native and knew the key players in Latin America on a first name basis.
In 1940, Rockefeller came up with the Good Neighbor Policy, which history books assign to FDR because it was executed on his watch. The logic was based on the international situation of that period. We had been treating our neighbors in this hemisphere as vassals, which caused no small level of resentment. Now we would treat them as equals.
It was becoming evident that we were going to go to war with Germany and Japan in the near future. It was best to get our neighbors on our side rather than Germany’s or Japan’s before war broke out. Thus our new policy.
It is becoming evident today that when our economic collapse finally happens, the American people will need a narrative and an external enemy, lest American anger be vented on segments of its own population. We’re setting up Russia for a war and perhaps many nations of the BRICS alliance as well. If we’re really going to go to war, it would be a major mistake for an island 90 miles away from American shores to be used as a staging area for nuclear attack or even invasion. This is another reason why we’re bringing the Castro brothers into the family. As the old saying goes, “Keep your friends close, but your enemies even closer.”
The goal here is to make Fidel and Raul our communists, rather than communists loyal to our enemies across the globe. It’s a recognition of just how perilous things are becoming.