Obama’s Vision for Relations with Cuba

In his final year as president, President Obama is receiving hard-earned praise for the actions that he has taken during the past eight years. Some of this praise has been retrospective—such as, perhaps most notably, the op-ed that conservative pundit David Brooks published in The New York Times entitled “I Miss Barack Obama,” in which he details his own surprise at how much he misses Obama as a presidential candidate amidst the chaos that is the 2016 primaries. Commentators from both sides of the aisle are saying that the president is finally coming into his own and taking chances, a trend that many trace back to a week in June of 2015, during which he managed to secure historic victories on trade, health care, and same-sex marriage. But, in fact, one of the president’s boldest policies began in 2014, when he announced that the United States would start down the long road towards normalizing relations with Cuba. In spite of conservative backlash that the president has been legitimating corruption and ignoring the oppression of democracy-promoting Cubans in his actions, Obama understands that the only way to move forward with Cuba is to work with the current government while also tactfully broaching the reality of its failings.On December 17, 2014, both Obama and Cuban President Raúl Castro made statements officially announcing that there would be a new course in US-Cuba relations. On July 20th, 2015, the US embassy in Havana and the Cuban embassy in Washington reopened. In March 2016, Obama went on a historic official visit to Cuba. He was the first sitting US president to travel to Cuba since Calvin Coolidge went in 1928.

In his Atlantic article on Obama’s presidency, entitled “The Obama Doctrine,” journalist Jeffrey Goldberg evaluates the president’s toughest foreign policy decisions from both Obama’s perspective and those of his advisors and critics. Goldberg interviews Ben Rhodes, a deputy national security advisor in the administration. Rhodes explains that the turning point in respect to Cuba, at least symbolically, was when Obama encountered President Castro at Nelson Mandela’s funeral in December 2013. The president chose to shake Castro’s hand, marking the onset of a tonal shift between the two governments. Obama’s theory regarding Cuba boils down to a few main points: one of which is that America has been known to “make ourselves a prisoner of our own history.” Though we do have a complicated relationship with the communist nation, the embargo simply was not working for either side. Stringent trade restrictions punished the Cuban people and impaired their economy. And, despite our frozen relationship, the Castro family has remained in power since the embargo began in 1962.

Obama recognized both the short-term and long-term opportunities that normalizing relations with Cuba presents. Travel by American citizens and trade with the United States will have an immediate impact on the Cuban economy. Contrary to the claims of conservative criticism, eliminating the travel restrictions also serves the interest of American citizens. In his “Wake Up America” monologue, conservative television personality Eric Bolling lambasted Obama’s March 2016 trip to Cuba, arguing that the president has lifted sanctions and travel bans in Cuba while gaining nothing for the American people in return. This claim implies that sanctions were single-directional and that Americans have no interest in traveling to Cuba. This is simply not true. The Guardian reported in May 2015 that US travel to Cuba had surged 36 percent since the thaw in diplomatic relations was announced in 2014. The numbers for 2016 are still unknown but expected to be even higher now that commercial flights will run from select American cities. In short, the economic benefits of the thaw are by no means one-sided. There is clear demand for tourism and trade with Cuba.


Looking beyond these short-term impacts, the more long-term, visionary aspect of Obama’s Cuba policies is his belief that restoring relations will create an opportunity to improve the status of human rights and the potential for democracy in Cuba over time. At present, the Cuban government continues to repress dissent and censor public criticism. Human Rights Watch reports that the Cuban government relies on “arbitrary detention to harass and intimidate individuals who exercise their fundamental rights.” Furthermore, the government has long held hundreds of political prisoners. Even following a conditional release of many of these individuals in 2014, “dozens more remain in Cuban prisons,” according to local human rights groups. The Cuban government controls all media outlets and maintains tight restrictions on access to outside information. In recent months, however, the Castro government has set up dozens of pay-as-you-go WiFi hotspots that are accessible to all—not just tourists and officials—which constitutes a definitive sign of progress toward openness. Nevertheless, these aspects of Cuban society under communism are not likely to change rapidly. The US government is aware of this fact. But, essentially, Obama believes that working with the Cuban government has more potential to spark change than the alternative of continuing the embargo. The stagnant policy of isolation and pressure has been in place since 1960 and has not yet proven successful.

On the broader stage of Latin American politics, improving relations with Castro will be deeply meaningful to onlooking leaders in countries such as Argentina, Venezuela and Bolivia, where anti-American sentiment has long been prevalent in mainstream politics. To be absolutely clear, Obama is not seeking to impose new leadership in Cuba, as other, more interventionist policy makers might advocate. Cuba remains under Castro communism and will remain so for the foreseeable future. But Obama’s logic is that the Cuban people’s increased access to information and commerce will affect Cuban politics in the long run.


From March 20th to March 22nd, 2016, Obama took the first official trip of a sitting American president to Cuba since 1928. His itinerary included a visit to the memorial of Cuban revolutionary hero Jose Martí, a one-on-one meeting with President Castro, government meetings, a state dinner in the Palace of the Revolution, and a historic baseball game between the Tampa Bay Rays and the Cuban National team. On the third day of the trip, when the president was scheduled to attend the baseball game before departing Cuba to continue on to Argentina, three coordinated nail bombings took place in Brussels, Belgium. Thirty-two people lost their lives and about 200 people sustained injuries. The Islamic State of Iraq and the Levant (ISIL) took responsibility for the attacks. When it was announced that Obama would attend the baseball game and would not be cancelling his trip to Argentina, he was widely critiqued by conservative commentators and presidential candidates. In an interview at the baseball game, Obama said that taking action to change his itinerary would be playing right into the terrorist’s hands. In saying this, the president demonstrated at once his commitment to diplomacy in Latin America and his measured and pragmatic response to terrorism.

Since his meetings with Castro and the Cuban government, Obama has also been criticized for the visibly tense interactions. "In effect, President Obama is the purveyor of what I call 'limp-wristed diplomacy,” said Bolling, referencing what he characterized as a cringe-worthy photo of Obama and Castro's awkward handshake. "How appropriate that the president's limp wrist is being held up by a communist despot,” he jabbed. Yes, Castro and Obama’s encounters may have been awkward. It is only inevitable that, after 60 years of embargo, relations between these nations would be uncomfortable at first, especially given America’s distaste for the Castro family. But is stomaching uncomfortable encounters not what diplomacy is all about? And how can Obama be criticized as limp-wristed when he took decisive action to normalize relations in the face of a long-enduring, ineffective policy?

Former Republican presidential candidate Ted Cruz, whose Cuban family has been targeted for opposing the Castro regime, called Obama’s trip a “sad day in American history.” Speaking to reporters in Peoria, Arizona before Obama’s trip, Cruz said that the president visiting the country before it is a “free Cuba,” was a diplomatic failure:

Ya know, this is an issue I know firsthand. My family has experienced the ravage of Cuba. My father fought the Cuban revolution. My father was imprisoned and tortured as a teenager by Batista. And my aunt, my tía Sonia, was imprisoned and tortured by Castro’s goons. Now when President Obama is in Cuba, you know who he’s not going to meet? He’s not going to meet the dissidents who are being tortured right now by Raúl and Fidel Castro, who are being silenced for daring to stand up. He’s not going to meet the Ladies in White.

One cannot deny the ongoing reality of oppression that the members of the opposition in Cuba face. The status of pro-democracy fighters in the country is a grave human rights injustice, of which Obama is well aware. In fact, while in Cuba, he did meet with dissidents—including the Ladies in White, a group that was created in 2013 by the wives of political prisoners. In a meeting with members and other dissident groups at the US embassy in Havana, he praised their “extraordinary courage” in the face of the Castro regime’s mass detention of political prisoners. The president chose to meet with these individuals in order to ensure that policy regarding Cuba takes into account the voice of the Cuban people—not just the Cuban government. Obama also directly addressed the ideological differences between Cuba and the United States in his remarks at the Gran Teatro de la Habana in Havana. After expressing regret over the inefficacy and hostility of the embargo, the president acknowledged persistent ideological tensions: “We cannot, and should not, ignore the very real differences that we have—about how we organize our governments, our economies and our societies,” Obama said. “Cuba has a one-party system; the United States is a multiparty democracy. Cuba has a socialist economic model; the United States is an open market. Cuba has emphasized the role and rights of the state; the United States is founded upon the rights of the individual.”

It is undeniably difficult for Obama to balance the Castro regime’s repression of dissident groups with the effort to normalize relations with the Cuban government. But Cruz’s comments ignore the fact that Obama’s actions also seek to address these issues over time by working with the current Cuban government. As president, Obama needs to collaborate with the Cuban government and, at least at present, that means not undermining them by supporting dissidents, no matter how much more closely some of those groups may align with American values. Obama’s choice to renew relations with Cuba does not degrade his commitment to American values of individualism, democracy, and freedom of speech. While there is no certainty moving forward that Obama’s policies will have an impact on democracy in Cuba, it is more likely to inspire change than an almost 60-year-old embargo. In a speech on July 1, 2015, Obama said that he did not expect Cuba to transform overnight but that he did believe American engagement—through the reopening of the embassy, reestablishment of business relationships, and renewed communication between Cuban, American, and Cuban-American people—is the best way to support democracy and the status of human rights in the future.

While the immediate effects of Obama’s Cuba policies are promising, clearly the long-term impacts of these decisions remain to be seen. They could result in failure, as conservative critics suggest, or they could lead Cuba and the US further along the winding road to a fully recovered relationship. In any case, recovery will take time and Obama is the first to acknowledge this fact. Following the president’s visit, Castro reportedly referred to the United States as an “enemy threatening the communist regime.” In America, many people cling to a Cold War-era image of Cuba as an example of the dangers of communist failure. It will take time for these perceptions to evolve. What is indisputable is that Obama took bold and decisive action regarding Cuba. His decisions were audacious, yet they were not impulsive—in fact, they were calculated. Obama knew that choosing to normalize relations would be controversial given Cuba’s political system, yet he understood that the embargo had resulted in a stalemate that could not go on. Thus, the president’s actions in Cuba are a testament to his tactful foreign policy, which is rooted in a commitment to patience and progress.