Making-Up Is Hard to Do: Obama’s ‘New Approach’ to Cuba

August 16, 2011

Speaking in August 2007 at a political rally in Miami’s Little Havana, the citadel of Cuban American conservatism, Senator Barack Obama called for a new U.S. approach to Havana. “We’ve been engaged in a failed policy with Cuba for the last 50 years,” he declared. “And we need to change it.”1 Campaigning for the votes of moderate Cuban Americans, Obama promised to end restrictions on remittances and family travel, resume “people-to-people” contacts, and engage Cuba on issues of mutual interest. It proved to be a winning strategy. Obama won 35% of the Cuban American vote (compared to 25% for John Kerry in 2004), and he carried Florida.2

As President Obama took the oath of office in January 2009, conditions for a rapprochement between Cuba and the United States appeared to be more propitious than at almost any time in a half-century. On the eve of the Fifth Summit of the Americas the following April, Obama ended restrictions on Cuban American remittances and family travel to Cuba, as promised. At the summit, Obama declared his desire to forge a new “equal partnership” with Latin America. When the region’s heads of state made Cuba policy a litmus test, he reiterated his commitment to a new policy of engagement. For his part, Cuban president Raúl Castro declared Cuba’s willingness to talk with the United States about “everything they would like to talk about, but on an equal footing, with absolute respect for our sovereignty and for the right of the Cuban people to their self-determination.”3

Two months later, the 39th General Assembly of the Organization of American States voted to repeal the 1962 resolution that suspended Cuba from its ranks—a resolution that served as the symbolic cornerstone of Washington’s policy of excluding Cuba from the hemispheric community. The United States supported the repeal in exchange for language that required Cuba to accept “the practices, purposes, and principles of the OAS,” including, implicitly, the commitment to democracy embodied in the Santiago Declaration of 1991.4 Cuba declined the invitation.

At the U.S. Interests Section in Havana, U.S. diplomats turned off the streaming electronic news billboard that so annoyed Cuban officials, and the Cubans took down the phalanx of 300 black flags erected to obscure the billboard. The State Department requested a resumption of talks on migration, which were suspended by President George W. Bush in 2004. Havana accepted, and the talks resumed.

The Obama administration also moved to restore the cultural and academic linkages that the Bush administration worked so assiduously to sever. Cuban scholars who had been denied permission to travel to the United States for a decade were granted visas, and cultural exchanges flourished once again. Colombian pop star Juanes gave a concert to a million young Cubans in Havana’s Plaza de la Revolución in September, and the following May Cuban singer Silvio Rodríguez played Constitution Hall of the Daughters of the American Revolution in Washington.

Deputy Assistant Secretary of State Bisa Williams traveled to Cuba for talks on restoring direct mail service in the fall of 2009 and was given “unprecedented access to its state institutions,” according to Jonathan Farrar, chief of mission at the U.S. Interests Section in Havana. Vice Minister of Foreign Affairs Dagoberto Rodríguez told her explicitly that by such positive treatment, “we meant to show our readiness to move forward in our relationship,” according to a leaked diplomatic cable.5

It looked as if Obama was proceeding step-by-step, albeit cautiously, toward a new Cuba policy, and Havana was receptive. But there were clouds on the horizon.


When Obama lifted travel restrictions on Cuban Americans, he did not lift the restrictions that Bush imposed in 2003 and 2004 on academic and people-to-people travel (educational travel by non-governmental organizations other than universities). A proposal to restore travel policy to the pre-Bush status quo ante took two full years to overcome internal opposition and finally emerged from the White House only after the 2010 midterm elections. Cuba remained on the State Department’s list of state sponsors of terrorism, despite the continuing dearth of supporting evidence. Perhaps most important, the Obama administration continued to allocate $20 million annually to fund USAID’s semi-covert “democracy promotion” programs aimed at Cuba.

Then, in December 2009, Alan P. Gross, a USAID contractor, was arrested in Havana for distributing sophisticated satellite communications technology to dissidents. The Gross arrest marked the end of the U.S.-Cuba “honeymoon,” such as it was. Washington declared that no further progress could be made until Gross was released, and some U.S. officials speculated that the arrest signaled Cuba’s lack of interest in better relations. “It is my personal belief that the Castros do not want to see an end to the embargo and do not want to see normalization with the United States,” Secretary of State Hillary Clinton said shortly after the arrest.6

The view from Havana was rather different. Although the Cubans initially had high expectations that Obama would truly change U.S. policy, they quickly became disillusioned by the slow pace. Nor were they willing to give Obama much credit for his early initiatives. Ending restrictions on Cuban Americans was a campaign debt he owed to Miami, done for internal political purposes, and hence was not seen as a signal of goodwill toward Havana. Obama’s rhetoric at the Summit of the Americas and Washington’s support for repealing the 1962 OAS resolution were written off as forced on him by Latin America.

Most important, the basic thrust of Obama’s policy was actually no different than past U.S. policy: Any U.S. move toward normal relations and lifting economic sanctions would require Cuba to move toward political democracy and free-market economics. “The Cuban people are not free. That’s our lodestone, our North Star, when it comes to our policy in Cuba,” Obama told reporters at the Summit of the Americas.7 That attitude, declared National Assembly president Ricardo Alarcón, was nothing more than “the continuation of an illegal, unjustifiable and failed policy.”8

The second year of Obama’s Cuba policy was a year of waiting. The State Department waited for the Cubans to put Gross on trial (and then, it hoped, sentence him to time served and send him home). When state prosecutors finally did put him on trial in March 2011, more than a year after his arrest, he was convicted of subversion and sentenced to 15 years in prison—a far harsher punishment than U.S. officials had expected.

The White House waited to see if Congress would vote to lift the travel ban on travel to Cuba, thereby relieving Obama of the political heat for promulgating new regulations to restore people-to-people travel. But the “freedom to travel” advocates could not muster the votes to even get the proposal to the House floor, a display of political weakness that made the White House even more reluctant to act unilaterally.

And Havana waited, in vain, for a U.S. response to the government’s unprecedented dialogue with the Catholic Church about human rights and political prisoners, a dialogue opened by Raúl in May 2010, which led to the release of almost all the island’s prisoners of conscience. Obama had declared in 2009 that before he took any further initiatives, “Cuba has to take some steps, send some signals,” such as freeing political prisoners and expanding freedom of religion.9 When the Cubans actually did these things, they expected some positive U.S. response. They were puzzled and chagrined when their actions met with nothing but silence.


On the surface, the arrest of Alan Gross halted any forward momentum in U.S.-Cuban relations, but it was more a symptom than a cause of the stalemate. By December 2009, the initial flurry of U.S. gestures had subsided, and relations were already slipping back into business as usual. After Obama fulfilled his campaign promise to lift restrictions on Cuban Americans, debated Cuba with Latin American heads of state at the Summit of the Americas, and supported a repeal of the 1962 OAS resolution, the president’s foreign policy team felt as if they had “done” Cuba. In fact, they had not come close to “resetting” relations with Havana the way they had reset relations with Moscow. U.S. officials had an inflated opinion of just how dramatically they had changed policy. Secretary of State Clinton called it “a completely new approach” and “the most significant policy changes toward Cuba in decades.” Obama himself used similar language.10 In fact, Obama’s policy was still more restrictive than that of either President Clinton or President Carter.

Having “done” Cuba, the administration moved on to other issues. Cuba, unlike Russia, could not command sustained attention from the president and his senior foreign policy officials, who confronted an imposing array of international problems: wars in Afghanistan and Iraq, nuclear proliferation in Iran and North Korea, China’s growing economic might, and, most recently, revolutions in North Africa. On the home front, Obama faced the Great Recession, the worst economic crisis since the 1930s; the Gulf oil spill, the worst U.S. environmental disaster ever; and bitterly partisan congressional battles over everything from the economic stimulus to health care, immigration, and the budget.

Even in the Western Hemisphere Affairs bureau at the State Department, Cuba was not at the top of the agenda. Senate Republicans prevented the confirmation of Arturo Valenzuela as the new assistant secretary until November 2009. With the bureau managed in the interim by Bush holdovers, no one was pushing from below for a new Cuba policy. By the end of the year, Valenzuela faced more urgent issues: repairing the diplomatic damage done by Washington’s equivocal response to the military coup in Honduras, working with Mexico to counter the surge in drug violence along the border, and coordinating relief efforts after Haiti’s devastating earthquake.

In short, Cuba was not a problem so urgent and acute that it demanded policy makers’ attention. That said, the more fundamental obstacle to improving U.S.-Cuban relations is the simple fact that Obama’s Cuba policy, despite being cloaked in the rhetoric of change, shared two premises common to U.S. policy since the end of the Cold War: (1) Significant progress in bilateral relations can come only if Cuba dismantles its political and economic system, replacing them with a multiparty electoral democracy and a free-market economy, and (2) even the smallest steps toward reducing tension have to be met by reciprocal steps from the Cuban side.


The first premise dates back to President George H.W. Bush. As the curtain came down on the Cold War, Cuba disengaged militarily from Africa and forswore promoting revolution in Latin America. Cuba’s security relationship with Moscow disappeared along with the Soviet Union. With that, the principal issues that U.S. presidents since Dwight D. Eisenhower had cited as obstacles to normalizing U.S.-Cuban relations disappeared. Sensing Cuba’s vulnerability, Bush added the new condition that normal relations depended on the demise of Cuba’s socialist system. In 1996, that conditionality was written into law in the Cuban Liberty and Democratic Solidarity Act (also known as the Helms-Burton act).

From the outset, Obama echoed this demand. “A democratic opening in Cuba is, and should be, the foremost objective of our policy,” he wrote in a Miami Herald op-ed piece in 2007. “If a post-Fidel government begins opening Cuba to democratic change, the United States . . . is prepared to take steps to normalize relations and ease the embargo.”11 Despite advocating a strategy of greater engagement with Cuba, he has never wavered from this core principle.

Conditioning better relations on regime change in Cuba makes any serious dialogue almost impossible. Since assuming the presidency in 2006, Raúl Castro has repeatedly offered to negotiate with the United States on the sole condition that the talks be conducted “in a spirit of equality, reciprocity and the fullest mutual respect.” He spelled out exactly what he meant by that early in the Obama presidency. “We are willing to discuss everything with the United States government, on equal footing; but we are not willing to negotiate our sovereignty or our political and social system, our right to self-determination or our domestic affairs.”12

George W. Bush’s policy was premised on a “big bang” theory of change in Cuba. Convinced that los históricos who made the revolution would never allow the model to change significantly, Bush officials sought to ratchet up economic pressure until the regime collapsed. It did not work any better for Bush than it had for his predecessors.

Obama’s call for a new policy suggested that he was more open to the idea of gradual, incremental change in Cuba. If Washington responded quickly and positively to any opening on the economic or political front, it might set in motion a self-reinforcing virtuous circle of gradually improving relations. The basic idea of reciprocity is not unreasonable in principle, but there has been an asymmetry of expectations. When Obama lifted restrictions on Cuban American travel, the administration regarded this as a major concession to Havana, deserving of some significant Cuban response. When none was forthcoming, the administration concluded that the Cubans were not serious. Similarly, when the Cuban government released political prisoners and initiated major economic reforms, there was no U.S. response, convincing Havana that Obama was not serious.

A strategy of reciprocity requires that each side respond quickly to actions by the other so that the linkage between action and response, even if not stated explicitly, is nevertheless clear. The flaw is that this strategy is constrained by domestic politics, especially (though not exclusively) in the United States. Opponents of improving relations will focus on blocking reciprocal action, thus bringing the process to a halt.

The 2010 battle over people-to-people travel regulations is a case in point. When the Cuban government and Catholic Church announced their unprecedented agreement on the release of political prisoners, Obama had a perfect opportunity to make a reciprocal response. A plan to restore people-to-people travel and expand academic exchanges had been developed in the State Department and vetted through the bureaucracy, and was awaiting presidential action. But Obama’s hand was stayed at the behest of Florida Democrats, who feared that any gesture toward Cuba might hurt them in the upcoming midterm congressional elections in the fall.

It was only after the elections, in January, that Obama promulgated the new regulations. But by then, the linkage to Cuba’s prisoner release had been lost. Moreover, after the Republican “shellacking” of Obama in the elections, the political terrain looked bleak for any positive movement on Cuba policy. In the Republican-controlled House, Cuban American representative Ileana Ros-Lehtinen (R-Fla.) took over as chair of the House Foreign Affairs Committee, and in the Senate, Bob Menendez (D-N.J.) was joined by Marco Rubio (R-Fla.), a Cuban American even less disposed toward better relations with Havana than Menendez himself.


If Obama was unwilling to take truly bold steps in 2009, when the political wind was at his back, it seems doubly unlikely as he heads into what will be a tough reelection fight. The best one can hope for is a gradual deepening of cooperation with Cuba on issues of mutual interest, like immigration, counter-narcotics, and environmental protection. WikiLeaks cables indicate that Cuban officials have repeatedly suggested closer cooperation in all these areas since Obama took office.13

Yet even on these apparently safe issues, the administration has proved surprisingly timid. The Spanish petroleum company Repsol is on the eve of beginning deepwater drilling in Cuban commercial waters, fewer than 100 miles off Florida’s coast. Cooperation with Cuba on oil drilling safety is an obvious need, especially in light of BP’s Deepwater Horizon disaster. But when the Department of the Interior held an international conference on drilling safety in April, Cuba was not invited.14

President Carter’s surprise trip to Cuba in April was intended to reinvigorate relations. At his closing press conference, Carter called for ending the U.S. embargo, lifting the travel ban, reestablishing normal diplomatic relations, and freeing both Alan Gross and the Cuban Five (Cuban intelligence agents imprisoned in the United States since 1998). To this, Raúl Castro commented, “I agree with everything that President Carter said.”15 Carter received a decidedly cooler response from the Obama administration, which gave him a polite hearing and then returned to business as usual—including $20 million in the new budget request for the “democracy promotion” program that landed Gross in jail in the first place.

The release of Gross might serve as a catalyst to jump-start the stalled relationship, but it is not clear what the Cubans want in exchange (except, of course, release of the Cuban Five, which they are unlikely to get). If Senator John Kerry (D-Mass.) has his way, USAID will have to radically restructure the Cuban democracy-promotion program, moving away from an explicitly subversive intent toward support for authentic social and cultural exchanges. The administration seems unwilling to revamp the program while Gross remains in jail, but changing the program may be exactly the quid pro quo the Cuban government wants for his release. One thing is certain: If “democracy promotion” continues unchanged, there will be more Alan Grosses. The recent Cuban TV series detailing State Security’s thorough penetration of the USAID programs spotlights the Spy vs. Spy ineptitude of an aid agency trying to run covert intelligence operations.

While Washington dithers, Cuba’s revolutionary leaders are marching forward toward a Cuban model of socialism that bears an uncanny resemblance to what China’s reform leader Deng Xiaoping called “socialism with Chinese characteristics”—that is, a mixed economy. Raúl Castro accelerated the pace of economic reform in 2010, announcing that as much as 20% of state workers held unnecessary jobs, and 10% of them would be laid off by April 2011 (though the pace of layoffs was later slowed). The following April, the Communist Party’s Sixth Congress approved a series of sweeping market-oriented reforms. No doubt, the Cuban government would prefer to undertake this politically risky transition in a more hospitable international environment, one in which relations with Washington were warming. But it is undertaking the transition nonetheless.

Meanwhile, the United States stands on the sidelines, disengaged and increasingly irrelevant to the changes under way on the island. In 1960, U.S. Ambassador Philip Bonsal argued for negotiating with Cuba’s brash young revolutionary leaders rather than breaking relations, on the grounds that severing ties would surrender any chance Washington had of influencing the trajectory of the revolution. Assistant Secretary of State Thomas Mann rejected the idea, declaring, “Our best bet is to wait for a successor regime.”16 More than 50 years later, Washington is still waiting.



William M. LeoGrande is Dean of the School of Public Affairs at American University in Washington. He is the author of Our Own Backyard: The United States in Central America, 1977–1992 (North Carolina University Press, 2000).



1. Brendan Farrington. “Obama Criticizes Cuba Policy at Little Havana Event,” the Associated Press, August 26, 2007.

2. Casey Woods, “Obama First Democrat to Win Florida’s Hispanic Vote,” The Miami Herald, November 6, 2008.

3. Raúl Castro, “Intervención en el segmento público de la VII Cumbre Extraordinaria del ALBA, Cumaná, Venezuela, 16 de abril de 2009,”

4. Organization of American States, General Assembly, “Resolution on Cuba,” AG/RES. 2438 (XXXIX-O/09), adopted at the Third Plenary Session, 39th Regular Session, held June 3, 2009, in San Pedro Sula, Honduras, Proceedings 1 (OEA/Ser.P/XXXIX-O.2, October 21, 2009): 12.

5. Jonathan D. Farrar (U.S. Interests Section Havana) to various recipients, “GOC Signals ‘Readiness to Move Forward,’ ” leaked cable, 09Havana592, September 25, 2009 (WikiLeaks).

6. Hillary Clinton, “Remarks on Nuclear Nonproliferation at the University of Louisville, Louisville, KY,” transcript, April 9, 2010,

7. Barack Obama, “Press Conference by the President,” transcript, Port of Spain, Trinidad and Tobago, April 19, 2009, Office of the Press Secretary, the White House,

8. Rob Gillies, “Cuban Parliament President Dismisses Obama,” the Associated Press, May 10, 2009.

9. “Interview of the President by Juan Carlos López, CNN en Español, April 15, 2009,” transcript, Office of the Press Secretary, the White House,

10. Hillary Clinton, “Remarks With Jamaican Foreign Minister Kenneth Baugh at CARICOM, San Pedro Sula, Honduras, June 2, 2009,” transcript,; Clinton, “Digital Town Hall of the Americas at FUNGLODE, Santo Domingo, Dominican Republic, April 17, 2009,” transcript,; Barack Obama, “Remarks by President Obama on Latin America in Santiago, Chile, March 21, 2011,” transcript, Office of the Press Secretary, the White House,

11. Barack Obama, “Our Main Goal: Freedom in Cuba,” The Miami Herald, August 21, 2007.

12. Nancy San Martin, “Raúl Castro Hints at Readiness for Dialogue With Washington,” The Miami Herald, August 19, 2006; Raúl Castro, “Key Address by Army General Raúl Castro Ruz, at the Ministerial Meeting of the Non-aligned Movement, Havana, Cuba, April 29, 2009,” transcript,

13. Jonathan D. Farrar (U.S. Interests Section Havana) to various recipients, “From the Mouth of MINREX: Possible Insight Into US-CU Migration Talks,” leaked cable, 09Havana341, June 6, 2009 (WikiLeaks); Farrar, “GOC Signals ‘Readiness to Move Forward,’ ”; Farrar to various recipients, “Cuban MININT’s Thoughts on Travel, Law Enforcement, and Intel Sharing,” leaked cable, 09Havana172, December 16, 2010 (WikiLeaks).

14. Tom Doggett, “U.S. Fears Cuba Oil Drilling, Mexico Suggests Talks,” Reuters, April 14, 2011.

15. The Carter Center, “Trip Report by Former U.S. President Jimmy Carter to Cuba, March 28–30, 2011,”

16. Thomas Mann to Philip Bonsal, September 27, 1960, box 2, fol. 2, Philip Bonsal Papers, Library of Congress.


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