Cuba’s communist political system, in power since 1959, is probably in its terminal stage. Beset by longstanding and gross economic mismanagement, deep-rooted corruption, and over half a century of U.S. economic sanctions, the island of eleven million is lurching toward an endgame for the ruling class. While China and Russia are willing to support the authoritarian government of President Miguel Díaz-Canel, they appear wary of committing too many resources to what increasingly appears to be a sinking ship. This begs the question—what is Washington’s Cuba policy? Is the U.S. government ready for political upheaval less than 100 miles from Florida? This becomes even more pressing considering Haiti’s meltdown, Venezuela’s security threat to Guyana, and the related hot-button issues around immigration and border control.

Cuban-American relations are complicated, with the policy debate long influenced by the Cold War. As historian Ada Ferrer, author of Cuba: An American History, observed: “The exigencies of the Cold War meant that for decades Americans generally understood Cuba primarily as a small—if dangerously proximate—satellite of the Soviet Union.” After the end of the Cold War in 1989, this has left opinions over the island sharply divided, with an influential bloc of largely Cuban-American and, more recently, Venezuelan-American voters, strongly opposed to the full normalization of relations with the regime in Havana. Close to these exile communities, the Republican Party has long maintained a hardline approach vis-à-vis Cuba, favoring prolongation of economic sanctions, with the view that such measures will eventually precipitate regime change. Moreover, Cuba has repeatedly demonstrated that it is not a friend of the United States, something most recently evidenced by the espionage scandal involving former U.S. diplomat Manuel Rocha, its willingness to allow China to establish a listening post on the island, and the alleged use of Cuban mercenaries in Russia’s war against Ukraine.

Arguably, the default in U.S. diplomacy toward Cuba has been a widening set of embargoes and a sanctions policy regime. This is also a core U.S. strategy vis-à-vis Maduro’s Venezuela and Ortega’s Nicaragua. Over time, this has resulted in the absence of the hard work of diplomatic statecraft. While embargoes and sanctions have an important role in shaping U.S. foreign and security policies, they have become substitutes for actual policy and strategy.

Cuba today is run by the Cuban Communist Party (Partido Comunista de Cuba or PCC), with President Miguel Díaz-Canel at the helm. A strong Castroite, Díaz-Canel succeeded Raúl Castro as the country’s leader in 2018 and, in 2023, was re-elected as president with a 97.66 percent vote from the National Assembly, unopposed.

Cuba is dominated by a small political elite built up around Díaz-Canel, including members of the Castro family, high-ranking officials of the PCC, the armed forces, and the civil service. While the Cuban government blames the United States for most of the island’s economic problems, its own repressive economic and political management contributes greatly to the country’s enduring woes. The cumulative effects of all this, plus the more recent effects of COVID-19, is a sinking economy. As one observer noted in January: “Cuba is going through its worst economic crisis in 30 years. Cubans have suffered falling wages, deteriorating public services, regular power outages, severe shortages, and a growing black market. Hundreds of thousands of people have fled the country.” This has left an undercurrent of discontent—in 2021 and 2024, the island was rocked by demonstrations, which were quickly crushed by security forces. 

The Díaz-Canel regime’s dilemma is that it remains caught between a collapsing economy that it appears incapable of rebuilding without undoing its own political control. In the political sphere, it faces a crisis of legitimacy that it is unwilling to address since this would undo the regime’s authoritarian dynamic. This is not sustainable. U.S. policymakers should take note and anticipate a need for greater creativity in our relations with Cuba. U.S. policy framed by over sixty years of intermittent points of crisis must change to reflect a changing geopolitical landscape in the Caribbean.

The Democratic Party has been more open to improved relations with Cuba. However, the Carter administration’s efforts to improve relations with Cuba were doomed by strategic miscalculations, which observed Cuba sending combat troops to help leftist allies in Angola (1975–1991) and Ethiopia (1977–1978). Fidel Castro’s use of the Mariel boatlift in 1980 to empty his country’s asylums and prisons and allow transit to the United States further eroded the Carter administration’s efforts at engagement.

It was not until the Obama administration that a more sustained effort was made to reduce tensions. Diplomatic relations were restored in 2015, a move welcomed by an economically desperate Castro regime. In March 2016, President Barack Obama became the first U.S. leader to visit the island since President Calvin Coolidge in 1928. The resumption of relations also came with a loosening of economic sanctions. The measured opening of the Obama administration, despite the Cuban government’s ongoing hostility toward the United States, allowed a greater flow of remittances into the country, proving to be vital for a country that struggled through much of the 1990s following the collapse of the Soviet Union’s generous assistance. At the same time, U.S. businesses responded favorably to the opening—especially airlines, cruise ship operators, and agricultural exporters—which created stakeholders. A fledgling Cuban private sector also benefited from the opening with the United States.

While generating considerable excitement at the time, the Obama opening seemed to lack an overall long-term political strategy beyond the need to tone down a crisis-prone and unproductive relationship. There was no clear-cut second act following the president’s visit to Havana. Indeed, little public discourse ensued, suggesting significant follow-up steps. Most notable was the absence of a democratic engagement strategy in the thinking of the Obama White House. Even if the tactical assessment in the aftermath of the Havana visit was that it was preferable to dwell on less sensitive issues (mostly related to commercial transactions), no actions seemed to follow that demonstrated a concern with Cuba’s undemocratic governance. An example of this would have been to name an activist U.S. ambassador, as was done in Eastern Europe in the 1980s. As it turns out, to this day, U.S. representation in Havana is led by a chargé d’affaires ad interim.

From this fragile political edifice, U.S.-Cuban relations plummeted with the advent of the Trump administration, which had a different perception of the world than the Obama administration—with the United States locked in a new Cold War with China using Cuba, Nicaragua, and Venezuela as its Western Hemisphere satraps. This newfound struggle between democratic, rule-of-law-guided countries against authoritarian regimes that do not play by the same rules animates the Trump administration’s attitude. This struggle now plays out in Venezuela, which supplied oil to Cuba and was provided with assistance in the form of Cuban doctors and security in return. The new Cold War perspective was given further impetus by China’s large role in Venezuela as well as the Asian country’s increasing business relations in Cuba from 2015 to 2017. This was significant as Venezuela’s ability to keep Cuba’s economy afloat faded rapidly following the collapse of oil prices in 2014–2015.

Any push for a new U.S. policy must consider domestic politics. President Trump astutely played to Florida’s staunchly anti-communist Cuban-American community. In June 2017, when speaking to members of that community, he announced: “Effective immediately, I am canceling the last administration’s completely one-sided deal with Cuba.”

President Trump promptly restricted travel to Cuba and sought to curtail American business dealings on the island that benefited the Cuban military, government, and intelligence services (which are owners of state-owned companies). In the last days of his administration, President Trump designated Cuba as a “state sponsor of terrorism,” citing Cuba’s continued harboring of U.S. fugitives, Havana’s refusal to extradite Colombian guerrilla commanders, and its support for Venezuela’s Maduro regime. Naturally, this also triggered a new set of sanctions.

When the Biden administration came into office in 2021, expectations were high that he would return to greater engagement with Havana. Biden did reverse some of his predecessor’s policies: flights between Cuba and the United States were resumed, family reunifications were allowed, remittances were permitted to flow again, and engagement on certain key issues—like migration and drug trafficking—could be resumed. However, the big rollback to the more open relationship initiated by Obama never occurred. Domestic U.S. politics factored in substantially, with Trump capturing Florida in 2016 and 2020 while other elections in the state also won by Republicans.

While Washington has hoped that Cuba will stay on the foreign policy backburner, dark clouds loom over the island. Dangerous policy inertia marks President Díaz-Canel’s regime and remains highly unpopular. Public discontent over a lack of food, power, and fuel is met by armed forces and a digital shutdown. China and Russia have both sought to step up their business with Cuba, but a lot more will be needed to stave off a further slide in the country’s fortunes.

What are the options for U.S. policy? One option favored by more progressive members of the U.S. political camp and the business community is to return to the engagement initiated during the Obama administration. The upsides promoted are that U.S. businesses (some of which sit in Republican states) would be allowed back into the country, and the Cuban population would have less animosity vis-à-vis the United States when the regime eventually changes.