Obama said that his operating theory was based on three premises. “No. 1 was, Cuba is a tiny, poor country that poses no genuine threat to the United States. No. 2, in this era of the Internet and global capital movements, is that openness is a more powerful change agent than isolation. That’s not always the case. There are unique circumstances, like North Korea, which is such a closed system that all you do there is reward those who are in power, and there’s no capacity to reach people.
“No. 3 was the belief that, if you are interested in promoting freedom, independence, civic space inside of Cuba, then the power of things like remittances to give individual Cubans some cash, even if the government was taking a cut, that then allowed them to start a barbershop, or a cab service, was going to be the engine whereby individual Cubans—not directed by the United States, not directed by the C.I.A., not through some grand conspiracy, but Cuban people—who now have their own little shop and have a little bit of savings can start expecting more.” [...]
The project, according to Obama and a number of his key advisers, started with the modest goal of tweaking a few regulations, but it evolved into an ambitious bid to open up Cuba’s closed system, by using seduction instead of force. For a generation brought up with the terror of the Cuban missile crisis, this meant abandoning a half-century-long crusade. Over the years, the United States had tried to dislodge the Castro regime by a variety of methods, including invasion, attempted assassination, funding dissidents, and a baroque plot to create a fake Twitter service that was intended to aid an antigovernment uprising. When Obama announced the opening with Cuba, John Boehner, then the Republican Speaker of the House, said, “There is no ‘new course’ here, only another in a long line of mindless concessions to a dictatorship that brutalizes its people and schemes with our enemies.” For a younger generation, though, it seemed obvious that commerce would triumph over politics. “We just don’t believe that rhetoric about changing the Cuban political system is constructive,” one of Obama’s aides told me. “And we don’t think it resonates broadly with the Cuban people, who are more focussed on their economic well-being.” [...]
I asked Obama why, considering Fidel’s long-standing distrust of the Americans, Raúl had finally stepped forward. “It’s my sense that two things are going on,” he said. “One is that there is a recognition—particularly in light of what’s happening in Venezuela—that sustaining their economic model over the next ten years becomes increasingly untenable. So they’re very much in the mode of: how do we make our economy run without giving up power?” He went on, “My impression also is that Raúl recognizes that any substantial change to their economic system—and, by extension, at least their civil society, if not their full political system—requires him to do the downfield blocking. If a younger generation tries to pull this off without the revolutionary credentials, there will be too much pushback.”
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