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Cuba and the Art of the Deal

One of the main criticisms of President Barack Obama’s opening to Cuba is that he did not extract any concessions from Raúl Castro on human rights—a criticism amplified whenever Cuban police break up a dissident meeting or demonstration. But making quid pro quo human-rights demands would have been a non-starter, just as it has been for the past 58 years. That approach would have made it impossible for the United States and Cuba to reach agreements on prisoner exchanges, diplomatic relations, and cooperation on issues of mutual interest.

Cuba always rejects such quid pro quo conditions, fearful that any concession will be interpreted as a sign of weakness. It’s a negotiating style that President Donald Trump will understand. “The worst thing you can possibly do in a deal is seem desperate to make it,” he wrote in The Art of the Deal [1]. “That makes the other guy smell blood, and then you’re dead. The best thing you can do is deal from strength.”

The idea that the best way to support a political opening in Cuba is for the United States to demand human-rights concessions as a condition of engagement is not just a bad negotiating strategy. It also represents a fundamental misunderstanding of how the United States can most effectively influence Cuba’s political future. Although Cuban leaders have always defiantly rejected direct U.S. demands, they change their behavior of their own accord when it serves their interests. In 1978, for example, knowing that human rights were a priority for President Jimmy Carter, Fidel Castro released 3,000 Cuban political prisoners in hopes of improving relations with Washington.

The U.S. policy of engagement follows a similar logic: rather than make demands Cuba is sure to reject, engagement aims to create conditions that provide Cuban leaders with self-interested reasons to allow greater political and economic freedom. Cuba’s interest in normalizing relations with the United States is economic—that’s what Mr. Trump calls leverage [2]. Building bilateral economic ties creates the incentive for Cuba to maintain an open flow of people and ideas, and to be more responsive to U.S. concerns on a whole range of issues, including human rights.


Engagement also gives U.S. diplomats greater opportunities to interact with Cuban civil society, including dissidents, and to travel around the island to assess conditions outside Havana and verify Cuban compliance with 1995 migration accord that prohibits persecution of illegal migrants returned to Cuba. In addition, U.S. and Cuban officials now have a human-rights dialogue in which broad issues and specific cases can be raised directly—something that did not exist before. Backpedaling on engagement would reverse these important gains.

As the Department of State’s 2016 human-rights report [3] documents, the U.S. and Cuban conceptions of human rights are far apart. Of particular concern to Washington is the arbitrary short-term detention of Cuban dissidents (a practice that has largely replaced the long prison sentences previously handed out). The fact that the number of detentions [4] in the last four months is half of what it was in the first eight months of 2016 (down from an average of 913 per month to 444 according to the Cuban Commission for Human Rights and National Reconciliation) does not excuse the mistreatment of people trying to peacefully exercise rights guaranteed under Cuba’s constitution. But neither should the harassment of dissidents obscure the progress in other areas, including the expansion of public space for civil discourse, increased access to information, and the growth of the private sector.

When Raúl Castro called for more open debate about Cuba’s problems in 2012, Cuban intellectuals launched spirited discussions, at first in print journals and magazines like Espacio Laical [5], Vitral, and Palabra Nueva [6], produced by the Catholic Church, and Revista Temas [7], a journal of social and cultural criticism that tackles sensitive topics like inequality, racial discrimination, the role of religion, and the nature of socialist democracy. Even the official newspaper Juventud Rebelde [8] began conducting investigative reports of official malfeasance and corruption.

As internet access and cell-phone availability have expanded, these discussions have moved online. More and more Cubans have access to new sources of digital information and connect with one another via social media. Blogs and digital journalism [9] have appeared—dissident, officialista, and everything in between—engaging in debates and polemics in the expanding digital town square.

While internet access in Cuba continues to be limited, Freedom House, a staunch critic of human-rights abuses on the island, acknowledges that access has improved (albeit slowly) since 2013. Their annual “Freedom of the Net” report [10] shows that Cuba has made progress on all indicators of internet freedom—internet penetration, obstacles to access, limits on content, and violation of the rights of users.

Since the summer of 2015 the Cuban government has established over 328 public wi-fi hotspots [11] for Cuban users, and in December of 2016 Cuban officials signed an agreement with Google to improve internet speed on the island. At the same time, Cuba’s state-owned telecom company launched a pilot program to expand home internet access starting in Old Havana. It also lowered the price of internet access by 25 percent, thereby reducing one of the main obstacles to greater connectivity. The government plans to provide internet access to 50 percent of the population and mobile-telephone services to 60 percent by 2020. Increased access is helping reunite families, increasing information flows, creating new venues for public debate, and supporting the Cuban private sector.

Expanded travel also fosters the exchange of ideas. The policy of engagement has stimulated a rush of U.S. visitors to Cuba—almost 300,000 in 2016 [12], a 74 percent jump from the year before—in addition to the 330,000 Cuban Americans [12] who traveled to the island to visit family. Engagement has also brought Cubans to the United States—scientists, journalists, artists, and students. Some 40,000 them [13] visit the United States annually on non-immigrant visas. These exchanges are possible because the U.S. government relaxed restrictions on travel to Cuba to encourage people-to-people engagement, and the Cuban government lifted the requirement that Cubans get its permission before traveling abroad. 

Equally important, though it gets less attention, is how engagement fosters greater economic freedom. In recent years, Cubans have enjoyed new opportunities to open small private businesses and cooperatives, and they’ve rushed to take advantage of it. The number of private businesses has increased more than 300 percent in the past six years, and the private sector’s share of the labor force [14] has expanded to 28 percent, with plans to reach as much as 50 percent in the future. Most of the seed capital fueling this entrepreneurial boom [15] comes from remittances that Cuban Americans send to relatives on the island, and the supply chains for many of these new businesses reach back to south Florida. These linkages are a direct result of U.S. engagement. That’s why more than 100 Cuban private entrepreneurs wrote a letter [16] to President Trump asking him not to abandon them by cutting off those lifelines.

In short, U.S. engagement with Cuba is fostering and reinforcing positive developments on human rights in myriad ways, expanding the flow of information, ideas, people, and capital—all of which nurture Cuba’s expanding public discourse and vibrant entrepreneurial sector.

After the U.S. election, President-elect Trump declared [17] he wanted a new deal with Cuba that was good for the Cuban people, Cuban Americans, and the United States. A return to the policy of hostility fails that test because Cuba will predictably respond just as Donald Trump himself advises [18]: when attacked, “Fight back: Always hit back against critics and adversaries,” harder than they hit you. That leads to a dead end of perpetual antagonism. On the other hand, a policy of engagement built on the bedrock of everyone’s self-interest will produce the best deal possible and set the stage for even better ones in the future. Tough talk is cheap, but at the end of the day, as The Art of the Deal [19] notes, you have to “deliver the goods.”

William M. LeoGrande is professor of government at American University in Washington, DC, and co-author with Peter Kornbluh of Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana [20] (University of North Carolina Press, 2015). Marguerite Rose Jiménez is the senior associate for Cuba at the Washington Office on Latin America. She has spent the past 12 years working on Cuba in NGOs, think tanks, academic institutions, and most recently the U.S. government.

13 Comments (Open | Close)

13 Comments To "Cuba and the Art of the Deal"

#1 Comment By Interguru On April 19, 2017 @ 3:25 am

Why is Cuba a special case for human rights when we have strong relations with much worst offenders such a Saudi Arabia which beheaded 157 people in 2015, many for arbitrary offences? ( [21] ).

#2 Comment By Jason Poblete On April 19, 2017 @ 5:45 am

U.S policy toward Cuba is much more than human rights; in fact I’ve said for decades it is one of many issues, but that people have forgotten about. It about U.S. security and foreign policy interests, of which there are many.

And, most importantly, it is also about the billions of dollars that Cuba owes hundreds of thousands of American families for properties, homes, and businesses that Communist Cuba stole when it took over the island. Want a deal? The claims must be compesnated, or on the path to compensation.

As far as travel being a good thing, I generally agree; however, in the case of Communist Cuba it will not, never will, change a thing. Communist Cuba has been trading with the rest of the world for decades. Communist Cuba has traded with other nations, for decades.

Your piece, as others written including your book, are aimed at helping keep the Communist and Socialists in power, not helping the Cuban people break with the system that has kept the island enslaved politically, economically, and socially since 1959.

#3 Comment By Fran Macadam On April 19, 2017 @ 8:00 am

“It also represents a fundamental misunderstanding of how the United States can most effectively influence Cuba’s political future.”

It it is a misunderstanding not to realize that influencing foreign politics is the fundamental American obsession.

#4 Comment By Johann On April 19, 2017 @ 9:07 am

Actually, Cuba has little or nothing for us, so why bother? Its up to the people of Cuba to make any changes.

#5 Comment By Kurt Gayle On April 19, 2017 @ 9:55 am

From the Nov 29 2015 Reuters article that you link to: “During Trump’s campaign for the White House he had said he thought restoring diplomatic ties with Cuba was fine but that Obama should have cut a better deal…Later in the campaign, he toughened his rhetoric, seeking to reassure Cuban-American voters in Florida that he opposed Castro and his brother, Raul…”

Hopefully, both the “Obama should have cut a better deal” standard Trump campaign one-liner and the tough Trump anti-Castro talk were aimed more at getting out the Cuban exile vote in Florida than at setting President Trump’s future US-Cuba policy.

On the other hand, many older Cubans – those who remember what Cuba was like before Castro, who are intensely proud of the amazing things that the Cuban people have accomplished since the revolution, and who are worried that “the Americans will take over the island again” – would not be unhappy to see a very gradual, very cautious re-establishment of US-Cuba ties.

#6 Comment By cka2nd On April 19, 2017 @ 11:48 am

Jason Poblete says: “And, most importantly, it is also about the billions of dollars that Cuba owes hundreds of thousands of American families for properties, homes, and businesses that Communist Cuba stole when it took over the island. Want a deal? The claims must be compensated, or on the path to compensation.”

I hope this never happens, just like the loyalists to the British crown were never compensated for the property expropriated from them by the victorious American revolutionaries, right before they were exiled from their homes. In fact, the United States would be a far better place if the Confederate planters and politicians who led the South in secession had been dealt with using equally harsh measures. I have no great love for the Castro government, but handing the country back to its former elites is a recipe for turning Cuba into Honduras or Columbia, a hell for its workers and small farmers.

#7 Comment By Erik Shay On April 19, 2017 @ 1:10 pm

US Cuba policy has been determined far too long by a selfish, greedy flange of Cuban immigrants who have milked the US taxpayer of billions with phony projects like Radio Marti, exploited the wet foot dry foot law, robbed US citizens of their right to travel and cluttered the news with false claims and information. Please, they have been given enough.

#8 Comment By Humberto Capiro On April 19, 2017 @ 1:24 pm

GLOBAL VOICE: Cuba Si, Google No: Cuban Officials Rumored to Reject Google’s Free WiFi Offer – 17 July 201 — Top Cuban officials allegedly have rejected an offer from Google to supply the island with free public WiFi throughout the country. Although neither the company nor the Cuban government has explicitly commented on the matter, multiple news sources seem to have drawn this conclusion from an interview in Juventud Rebelde (“Rebellious Youth”), the island’s long-standing youth newspaper. The interview featured Jose Ramon Machado, a contemporary of the Castro brothers, who after forty years at the helm of Cuba’s Union of Communist Youth appears as determined as ever to instill in young Cubans the values and morals of Cuba’s unique brand of Marxism. When the reporter asked Machado what he thought about the value of the Internet for Cuban youth, Machado’s response was clear: “Internet access is a great opportunity and at the same time a great challenge, because new technologies are novel and vital, not only for person-to-person communication, but also for development. Everyone knows why there isn’t more Internet [in Cuba]. It’s because of the high cost. There are those who would like to give us Internet for free, but they aren’t doing this so that Cubans can communicate with one another, rather they’re doing it with the goal of penetrating us on ideological grounds, in an effort to make a new conquest. We need to get Internet, but in our own way, recognizing that the imperialist intention is to use it as one more way to destroy the Revolution. [22]

#9 Comment By Humberto Capiro On April 19, 2017 @ 1:25 pm

THE ECONOMIST: Cuba and the internet – Wired, at last – Mar 3rd 2011
ACCORDING to government figures, only 3% of Cubans frequently use the internet, making the communist island the least connected place in the Americas. Those that do require patience: according to an industry survey, Cuba’s dial-up internet access is the world’s second-slowest, after Mayotte, a French territory in the Indian Ocean. Under the guise of rationing the use of bandwidth, internet access is banned in most private homes and censored in offices. In 2009 Barack Obama authorised American companies to provide internet services to the island. But Cuba showed no interest in exploring the possibility. Instead it turned to its ally and benefactor, Venezuela.

#10 Comment By Humberto Capiro On April 19, 2017 @ 1:28 pm

HAVANA JOURNAL : List of 201 legal occupations for small business entrepreneurs in Cuba

#11 Comment By Whine Merchant On April 19, 2017 @ 8:20 pm

cka2nd & Erik Shay are correct in that emotional wailing and political manipulation by vested interests has perpetuated a bad outcome for all but a very few. These same interests have much to lose and little to gain by improving relationships between these countries.

#12 Comment By Ellimist000 On April 19, 2017 @ 11:35 pm

@Jason Poblete

“And, most importantly, it is also about the billions of dollars that Cuba owes hundreds of thousands of American families for properties, homes, and businesses that Communist Cuba stole when it took over the island. Want a deal? The claims must be compesnated, or on the path to compensation.”

Piggybacking on cka2nd’s point, get back to me when the African-American Slavery and Socioeconomic Oppression Reparation Act is passed, then we can talk about compensating former Cuban/American elites that bled their own land dry.

Life happens, deal with it, and move on for the good of both nations.

#13 Comment By John Suarez On April 20, 2017 @ 1:39 pm

Ronald Reagan entered the White House in 1981 and re-imposed the Cuba travel ban, toughened economic sanctions undoing Jimmy Carter’s detente with Fidel Castro, in 1982 placed the Castro regime on the list of state sponsors of terrorism, and started Radio Marti to break through the communist monopoly with uncensored information for Cubans on the island.

When it finally went on the air in 1985 Radio Marti marked a before and after inside Cuba. At the time President Reagan hoped that Radio Marti would ”help defuse the war hysteria on which much of current Cuban Government policy is predicated.” The Castro regime’s response was to end an immigration agreement and suspend the visits to Cuba by Cubans living in the United States.The Hoover Institution in 1989 listed it as one of a 100 conservative victories. The Reagan Administration also named former Cuban political prisoner Armando Valladares Ambassador to the United Nations Human Rights Commission and made human rights in Cuba a priority there.

The end result was that for the first and last time Amnesty International, the International Committee of the Red Cross and the UN Human Rights Commission were able to visit Cuban political prisoners.