President Obama’s Reflections on His Pursuit of Normalization with Cuba      

Jon Lee Anderson, the author of a Che Guevara biography and a forthcoming book about Fidel Castro and the Cuban revolution, has written a fascinating article about President Obama and Cuba in The New Yorker.[1] It provides the following details about Obama’s March 2016 visit to the island and comments about his decision to seek normalization with Cuba beyond those already discussed in earlier posts.[2]

During his visit to Cuba, President Obama hosted an Entrepreneurship and Opportunity Event at La Cervecería (a beer hall) on Havana Harbor. Attending were invited American and Cuban entrepreneurs, government officials and journalists. Brian Chesky, the co-founder of Airbnb, told the group that Cuba was one of its fastest growing markets. In response to Obama’s question, he said his company was now valued at $25 billion after only eight years of operation, and Obama used this as an example of what could happen to a new business. Obama said, “Cuba should take ideas, steal ideas from wherever you see something working, not from where they are not. There are some economic models (like Cuba’s) that just don’t work. That’s just the objective reality. The American people are not interested in Cuba failing. We’re interested in Cuba being a partner with us.”

After Obama had departed the island, a member of Cuba’s security services said that this event was “as subversive as the Bay of Pigs.” Other Communist Party loyalists voiced similar opinions.

Later Obama admitted that he thought the Cuban pushback to his visit would be a lot stronger. The beer hall event, he said, intentionally bypassed the Cuban state in order to advertise and promote the possibilities of commerce freed of political constraint.

Obama also said after his trip that his decision to seek normalization with Cuba was based upon these premises: (1) “Cuba is a tiny, poor country that poses no genuine threat to the [U.S.]” (2) “In this era of the Internet and global capital movements, openness is a more powerful change agent than isolation.” (3) “If you are interested in promoting freedom, independence, civic space inside of Cuba, then . . . remittances to give individual Cubans some cash . . . that then allowed them to start a [business] . . . was going to be the engine whereby individual Cubans . . . can start expecting more.”

Important for Obama was growing up in underdeveloped Indonesia and “never [being] star-struck by revolution. [He believed that Cuba’s revolution had started because of good motives, but he] “was never persuaded that they had taken the right course of action.”

Obama also told Anderson that he believes Raúl Castro’s pursuit of normalization with the U.S. was based upon two conclusions. First, Castro recognized—“particularly in light of what’s happening in Venezuela—that sustaining their economic model over the next ten years becomes increasingly untenable. [Therefore,] how . . . [does he] make [the Cuban] economy run without giving up power. . . . [Second,] Raúl recognizes that any substantial change to their economic system, . . . their civil society, . . . their full political system—requires him to do some downfield blocking [i.e., preparatory work]. If a younger generation tries to pull this off without the revolutionary credentials, there will be too much pushback.”


[1] Anderson, The Cuba Play, The New Yorker at 42 (Oct. 3, 2016).

[2] See posts listed in “Obama & Cuba, 2007-2014,” “U.S. & Cuba Reconciliation, 2014-2015,” and “Obama’s Visit to Cuba, March 2016” in List of Posts to dwkcommentaries—Topical: Cuba.