Raúl is 82, and his brother Fidel is 87. Regime change in Cuba is imminent. They know it and Obama knows it. I cannot predict exactly what will ensue in Cuba when the Castros die, but their deaths will create an opportunity to normalize U.S.-Cuba relations — even if their successors retain Marxist ideology and a dictatorial government. Richard Nixon and Henry Kissinger proved that engagement of ideological opponents can work. The Cuban people, who have suffered particularly since the collapse of the Soviet Union, deserve to be part of the global economy. We Americans are partly responsible for their plight. We seized the country in 1898 and through decades of meddling created an atmosphere perfect for revolution. We orchestrated a disastrous, ill-advised attempt to reverse the revolution in 1961 — the Bay of Pigs affair — and then arranged for the island to be isolated out of fear that Communism would spread throughout Latin America. That worst nightmare of ours didn't happen in Latin America (or Southeast Asia), but don't assume it was a triumph of American foreign policy. The reprehensible way that we pulled the plug on Salvador Allende was a factor too.
Beyond Cuba, modernization of the Caribbean overall is important. Western civilization created the mess that much of the Caribbean is today. Haiti ranks 161st of 187 countries for which the Human Development Index is calculated. The General Accountability office just published an analysis that admitting Puerto Rico to statehood would cost billions; if you visit the Puerto Rican interior, away from San Juan and the beaches, you'd see why. Our demand for drugs has perverted Jamaica and other islands. Even the few nations that thrive, such as the Cayman Islands, are relics of colonialism kept afloat mainly by peculiar banking and tax regimes. And I don't see much difference between what the USA did in Grenada in 1983 and what the Russians are doing now in Crimea. Note that the UN overwhelmingly voted to condemn the USA's invasion of Grenada as "a flagrant violation of international law". Sound familiar? From the perspective of history, sadly, that's hardly a new tactic in the Caribbean.
For so many reasons, normalizing relations with Cuba is the right course.