In December 2014, President Barack Obama announced that the United States would begin the process of normalizing diplomatic relations with Cuba. It was a high point in his administration’s foreign policy, the beginning of a rapprochement between two nations that had been at odds since the 1950s. But soon after taking office in 2017, President Donald Trump blew up his predecessor’s efforts at détente—rolling back nascent travel, trade, and security initiatives and downsizing the newly reopened U.S. embassy in Havana. Just a little more than two years after the start of a historic thaw, U.S.-Cuban relations were frozen once again.

President Joe Biden has pledged to get U.S. Cuba policy back on track, but the United States’ neighbor across the Straits of Florida will test his administration in a number of ways. U.S. officials will have to salvage what they can from the Obama years and try to overcome the disruptions of Trump’s tenure. In some instances, they will have to lift sanctions (reimposed during the Trump era) without expecting reciprocal concessions—a tactic that served Obama well. And on the home front, Biden and his advisers will have to free themselves of the crippling fear of running afoul of angry Cuban American exiles, a political calculus that leads invariably to policy incoherence and diplomatic frustration.

But most important, the Biden administration should choose—as Obama did—to play the long game with Cuba. The island won’t suddenly become a liberal, capitalist democracy. But patient engagement with Cuba, including efforts to open its economy to the world, is much more likely to yield the results that decades of confrontation have failed to achieve.


Critics of Obama’s diplomatic thaw with Cuba often claim that the former president gave away the store without getting anything in return. But Obama’s Cuba policy was a remarkable success. Two years of détente helped generate measurable positive changes in the country. The lifting of long-standing travel restrictions allowed millions of Cubans to meet the United States’ best ambassadors: educated travelers who brought with them American ideals and values. These visitors spent lavishly, purchasing the services of independent entrepreneurs. Suddenly, Cubans with hard currency in their pockets enjoyed greater freedom from the state and from the Cuban Communist Party. These business startups injected a vibrant, exemplary new pluralism into Cuban life, building on the slow opening of the Cuban economy already in progress.

Détente with the United States also emboldened average Cubans to express their deep-seated reservations regarding Communist Party rule. Cubans gathered on their patios and on street corners to voice their frustrations with the 60-year-old regime. When Obama visited the island in March 2016, the example of a young, Black president inspired many Cubans to wonder why their country had not produced such leaders. Increasingly, prominent artists and religious leaders dared to articulate positions contrary to the official narrative.

In reversing Obama’s policy of open engagement, Trump rolled back travel freedoms and impeded Cuban Americans from sending remittances to friends and relatives. He reduced the U.S. embassy in Havana to all but a skeleton crew. And in an additional punitive measure, he allowed certain U.S. firms and Cuban Americans to file claims in U.S. courts demanding compensation from the Cuban government for properties expropriated in the wake of the Cuban Revolution. Unsurprisingly, Trump’s sanctions had no more success in advancing freedoms in Cuba or in recovering expropriated properties than had the previous five decades of unrelenting U.S. hostility. On the contrary, Trump succeeded only in deflating the many Cubans who Obama had inspired to feel, at least briefly, hopeful for a brighter future.


When Obama announced the normalization of bilateral relations in 2014, he cautioned against predictions of sudden, sweeping change. Rather, he took the long view, a combination of what might be labeled “structural optimism” and “strategic patience.”

Obama believed—with reasoned optimism—that stitching Cuba to the fabric of the global economy and exposing it to wider cultural trends would over time induce meaningful change. The country would be more likely to evolve toward an open, pluralistic society as more U.S. and international visitors arrived, as its growing private economy became more tightly linked to global markets, and as the use of Facebook, Twitter, and WhatsApp spread among its citizens.

Obama believed that stitching Cuba to the fabric of the global economy would induce meaningful change.

Obama imagined that this process was, to some degree, inexorable and that Washington should be more patient in its dealings with the Caribbean island. Cuba sits a mere 120 miles from Miami. Obama believed that the waves of democratic capitalism—if not impeded by U.S. sanctions—would gradually erode the foundations of communism. Eventually, historians would score the regime of Fidel Castro and his brother and successor Raúl as a quixotic aberration of the Cold War, not as a major ideological rival. Cuba was not comparable to distant, giant China; inevitably, it would rejoin the inter-American system of collaborating neighbor states in the Western Hemisphere, where the United States is the natural leader.

As a result of these overarching views, Obama did not demand tit-for-tat concessions from the Cubans (except in the exchange of political prisoners). Easing sanctions was an end in itself. It was in the United States’ interest to flood the island with American visitors, to further expose Cuba to global commerce, and to jump-start private entrepreneurship. Subsequent bilateral cooperation on security matters of mutual concern—immigration, counternarcotics, counterterrorism, environmental stewardship in shared waters, money laundering, and human smuggling—also clearly served U.S. interests. And it was decidedly in the United States’ interest to invite Cuba to join the Summit of the Americas process (the periodic convening of the Western Hemisphere’s presidents and prime ministers) to advance Cuba’s reintegration into the inter-American system. After all, Cuba’s exclusion from these high-profile summits had become a source of friction between the United States and other Latin American countries whose governments also felt that a policy of engagement with Cuba was far better than insisting on its isolation.

Obama was right to demand little if anything in return for taking steps that were so clearly beneficial to Washington. What would making more demands have accomplished? The Cuban case does not fit into the traditional diplomatic models of tough bargaining, in which the United States would be more careful about ceding ground while extracting concurrent concessions. And even if Obama had—for domestic political reasons—made more strenuous demands on Cuba, they would not have appeased a political opposition in the United States that cannot be appeased. For nothing short of the immediate collapse of the government in Havana will satisfy the yearnings of many Cuban American exiles.


Just as Trump reversed Obama’s policy of détente, so, too, can Biden return the United States to a policy of engagement with Cuba with a stroke of the pen. He can restore general licenses for travel, reauthorize Cuba-bound commercial flights and cruise ship lines, and remove dollar limits on cash remittances and gift parcels to the island nation. Biden can reopen diplomatic channels, restaff the U.S. embassy in Havana (along with providing adequate security for U.S. officials stationed there), and revive constructive bilateral dialogues on security issues. And he can revisit the 1994 migration accord whereby the United States agreed to grant Cubans 20,000 immigrant visas per year; the agreement created an orderly and safe immigration process, designed to avoid the loss of life at sea or today’s massing of desperate Cuban migrants at U.S. borders.

The Biden administration can unravel obstacles to academic, cultural, and educational exchanges. It can allow Cuban baseball players to join Major League Baseball without having to renounce their Cuban citizenship. Within the constraints of congressional legislation, Biden can encourage U.S. firms and the Cuban American diaspora to do business with independent entrepreneurs in Cuba and with certain state-owned enterprises, such as hotels and resorts, that are not directly run by organs of the security apparatus.

Cubans watch Biden's inauguration as the 46th president of the United States, in Havana, Cuba, January 2021 
Cubans watch Biden's inauguration as president of the United States, in Havana, Cuba, January 2021 
Stringer / Reuters

Through renewed engagement, the United States could regain some standing to broach human rights issues in Cuba—concerns that are best advanced in concert with European allies—but it must remember that deep structural reforms in the communist country will take time. Washington should therefore look for areas of fruitful cooperation. In the coming months, Biden is likely to initiate hemispheric coordination on combating COVID-19 and future pandemics. Cuba is rightly proud of its universal health-care system and biotechnological innovation and certainly warrants a seat at this table.

The Biden administration should also seek Cuban cooperation on addressing the humanitarian crisis and political stalemate in Venezuela. Cuban security advisers help the autocratic Venezuelan President Nicolás Maduro maintain his desperate grip on power—and in turn Cuba receives subsidized shipments of Venezuelan oil. Encouraging Cuba to press Maduro to enter into good-faith negotiations with his domestic opponents will require political courage: the international community, with U.S. approval, will need to guarantee Cuba’s petroleum supplies if Havana is to risk losing its allies in Caracas. As part of a package deal, the international community could also assist Cuba in developing its abundant clean energy resources, including wind and solar energy.


Biden takes office at a moment when Cuba is ripe for change. The island’s economy is flat on its back, hit hard by the pandemic-induced collapse of international tourism and by decades of state-led mismanagement. In dire straits, the government has pledged economic reforms to empower private and cooperative businesses, liberalize the agricultural sector, and allow state-owned enterprises some freedom to move, however hesitantly, toward a more market-friendly version of socialism. Most immediately, authorities have announced plans to unify the national currency (split between a local version and a version pegged to the U.S. dollar) and to devalue it, steps long advocated by reform-minded economists.

Normally, the Washington-based International Monetary Fund and World Bank assist economies in the midst of such fraught transitions, but Cuba is not a member of either body. The international donor community could still mobilize a small Cuba Technical Assistance Trust Fund, perhaps under UN auspices, to finance an international advisory mission of economic experts. If the Trust Fund experiment progresses, Washington could allow the IMF and the World Bank to consider Cuba’s gradual accession, first to receiving more robust technical assistance and then, eventually, to gaining full membership.

Biden takes office at a moment when Cuba is ripe for change.

At this point, however, Havana would have to make significant concessions. To gain access to international capital markets—and to secure greater political support for engagement within the United States—Cuba should negotiate a bilateral settlement regarding the property it expropriated years ago from U.S. companies and citizens. Interested U.S. firms should be allowed to swap their financial claims for attractive investment opportunities.

Both Cuba and the United States could benefit from closer commercial relations. The United States wants to guarantee the security of the global supply chains of its companies, especially in pharmaceuticals, medical devices, information technologies, and certain agricultural products. The nearby countries of the wider Caribbean basin, including Cuba, boast the advantages of geographic proximity and competitive costs. The Biden administration could turn to the Caribbean basin to tighten and protect supply chains and eventually, once bilateral relations had markedly improved, include Cuba in the effort—provided it met standards regarding security, transparency, and efficiency. Cuba seems increasingly ready to play this role. In 2013, it inaugurated Mariel, a new special economic development zone, precisely to attract foreign investment and business.

Strengthening these international connections would serve a larger strategic U.S. goal: it would bolster the reformers struggling within the Cuban establishment. Although the Cuban government is hardly transparent, the push-and-pull of reform efforts suggests disputes between orthodox hard-liners and more progressive, youthful factions. Ultimately, Cuba will be changed from within, not from without. Reform-minded factions within the Cuban political class and bureaucracies are more likely to move their country toward gradual, peaceful change than the isolated dissidents who have traditionally soaked up U.S. attention and support.


Biden faces one major obstacle to reviving and fine-tuning engagement with Cuba: entrenched opposition at home. During Obama’s presidency, many Cuban American families applauded the relaxation of travel restrictions and caps on remittances. But in today’s hyperpartisan political environment, such humanitarian measures are likely to elicit a firestorm of criticism. Some Republicans, for instance, will probably reframe the restaffing of the embassy in Havana—a move so obviously in Washington’s interest—as a gift to Cuban communism.

U.S. diplomats will be hamstrung if Havana sees them as reliant on the approval of a historically hostile lobby. Luckily, Biden can consult with the Miami exile community but does not have to grant it veto power over his Cuba policy. Last year’s U.S. presidential election proved that the Democrats can win the presidency without Florida. Biden’s industrial and job creation policies will seek to cement a path to victory through the Midwest, potentially allowing the Democrats to grudgingly accept that Florida—with two Republican senators, a Republican governor, and a Republican legislature—is painted bright red at least for the near future.

If he makes peace with ceding Florida, Biden can press ahead with the urgent task of reviving relations with Cuba. Once the diplomatic ice had been broken, Obama had only two years to work toward undoing over 50 years of deep hostility and suspicion. The Biden administration has at least four years to set Cuba policy on a firm new course. But to succeed, Biden must forget the angry exiles and remember the basic principles of structural optimism and strategic patience that Obama grasped so well.

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