Why US Policy Toward Cuba Was 'Self-Defeating'

In March, I drove with my family from the Cuban capital, Havana, to the colonial town of Trinidad, through the city of Cienfuegos. We were more or less the only car on a very rutted road. Cienfuegos is a city of roughly 150,000 people, but it seemed dead. Its buildings were in a state of decay—just like most of the neighborhoods of Havana—and goods were being moved by donkey cart. My wife and I explained to our children that this is what can happen to a people, and to an economy, under communist rule. We spent days trying to teach them about Cuba's dual-currency system—a dollar-based system for tourists, and a make-believe one for ordinary, sometimes-hungry Cubans—but they had difficulty understanding it, because it made so little sense.  

On the way to Trinidad, we made a quick stop at Playa Giron, the beach on the Bay of Pigs where a CIA-sponsored invasion ended in disaster. The place was a shambles; some of the faded signs at the decrepit hotel were in Russian. Near the beach was a tiny store that, like most Cuban stores, sold virtually nothing, except for Che Guevara T-shirts, and, unaccountably, Pringles and Coke. One of my daughters made for the Pringles. "Look," she said, "we won."

Critics of the Obama administration, and critics of the Castro regime, will say that today's decision to normalize relations between the two countries represents a victory for one-party rule. I think they are wrong; there is a very good chance that the U.S. comes out the winner in this new arrangement, and not only because Alan Gross is now home.

(Related: Obama Restores Diplomatic Ties With Cuba After More Than 50 Years)

It is difficult for a Castro to agree to normalized relations with the United States; anti-Americanism is a pillar of the regime. But looking around Cuba earlier this year, it was apparent that there was an opening for the Obama administration to change direction and actually influence the course of events inside Cuba.

President Obama—and Benjamin Rhodes, the National Security Council aide who led the negotiations with Cuba—saw an opportunity to open up Cuba to American influence, and they took it. They will be criticized mercilessly—they already are—for giving too much ground to the Cuban regime. But Obama and his team knew something that many previous administrations before them also knew: U.S. policy toward Cuba was self-defeating. Five decades of an embargo, five decades of hostility, had not dislodged the Castro brothers, and had not brought even a suggestion of democracy to the island.

Alan Gross's hapless mission to Cuba was proof of a dysfunctional, sclerotic, and mindless policy. The United States Agency for International Development, which is not a spy agency, sent an unprepared and untrained contractor to break Cuban law, by smuggling into Cuba banned telecommunications equipment. His mission was a vestige of Cold War thinking. The goal was to help Cubans communicate freely, even while under the thumb of an oppressive regime. The goal was not achieved.

Now, the U.S. has a better chance of achieving this important mission. Critics of Obama's Cuba initiative have a point: There is no way to guarantee the success, in human-rights terms, of this dramatic new opening. But time has discredited the alternative vision. The seemingly never-ending embargo did nothing to bring about the conclusion of the seemingly never-ending rule of the Castro brothers. After 50 years of trying one thing, and seeing that thing fail, and fail again, it was about time that the United States try something else.