Cuba has long been a major foreign policy challenge for the United States. President Biden is the latest U.S. leader to grapple with how to balance democracy promotion with the desire for a better bilateral relationship.
The U.S.-Cuba relationship has been plagued by distrust and antagonism since 1959, the year Fidel Castro overthrew a U.S.-backed regime in Havana and established a socialist state allied with the Soviet Union. During the half century that followed, successive U.S. administrations pursued policies intended to isolate the island country economically and diplomatically. The United States has sanctioned Cuba longer than it has any other country.
More From Our ExpertsPresident Barack Obama took some extraordinary steps to normalize U.S. relations with Cuba, meeting with leader Raúl Castro and restoring full diplomatic ties. However, President Donald Trump largely reversed course, hitting Cuba with a raft of new sanctions and redesignating it as a state sponsor of terrorism. The Joe Biden administration has eased some restrictions, but renewed anti-regime protests in Cuba, combined with the country’s worsening humanitarian situation and a massive wave of emigration to the United States, have further complicated the policy challenge.
The tumultuous U.S.-Cuba relationship has its roots in the Cold War. In 1959, Fidel Castro and a group of revolutionaries seized power in Havana, overthrowing the U.S.-backed government of Fulgencio Batista. After the Cuban Revolution, the United States recognized Fidel Castro’s government but began imposing economic penalties as the new regime increased its trade with the Soviet Union, nationalized American-owned properties, and hiked taxes on U.S. imports. After slashing Cuban sugar imports, Washington instituted a ban on nearly all U.S. exports to Cuba, which President John F. Kennedy expanded into a full economic embargo that included stringent travel restrictions.
The United States severed diplomatic ties with Cuba and began pursuing covert operations to overthrow the Fidel Castro regime in 1961. The missile crisis arose after Cuba allowed the Soviet Union to secretly install nuclear missiles on the island following a botched CIA attempt to topple Castro, known as the Bay of Pigs invasion. U.S. surveillance aircraft uncovered the Soviet installations in October 1962, setting off a thirteen-day showdown between Kennedy and Soviet leader Nikita Khrushchev that threatened to escalate into nuclear war.
Kennedy demanded that the Soviets remove the weapons and ordered the U.S. Navy to impose a maritime quarantine of Cuba to block additional arms from reaching the island. In the end, Khrushchev agreed to withdraw the missiles in exchange for a pledge from Kennedy not to invade Cuba and to remove U.S. nuclear missiles from Turkey. The crisis was a turning point in the Cold War, as the two superpowers made efforts to avoid nuclear confrontation.
More From Our ExpertsIn the decades that followed, economic and diplomatic isolation became the major prongs of U.S. policy toward Cuba. In 1982, President Ronald Reagan labeled Cuba a state sponsor of terrorism [PDF] for its support of leftist militant groups in Africa and Central America. Presidents George H.W. Bush and Bill Clinton signed laws—the Cuba Democracy Act of 1992 and Cuban Liberty and Democratic Solidarity Act of 1996, also known as the Helms-Burton Act—that strengthened U.S. sanctions and stated that the embargo would remain in place until Cuba transitioned to a democracy that excludes the Castro family and upholds fundamental freedoms.
Timeline: U.S.-Cuba RelationsSome adjustments in 1999 allowed for the export of U.S.-made medical supplies and food to the island. Restrictions tightened, however, under President George W. Bush, whose Commission for Assistance to a Free Cuba increased enforcement of existing sanctions.
During his 2008 presidential campaign, Barack Obama said isolating Cuba had failed to advance U.S. interests and that it was time to pursue diplomacy with the Castro regime. Several weeks after taking office, he eased restrictions on remittances and travel, allowing Cuban Americans to send unlimited money to Cuba and permitting U.S. citizens to visit Cuba for religious and educational purposes.
As Obama began softening U.S. policy toward Cuba, the island signaled an openness to reform under the new leadership of Fidel’s brother, Raúl. Facing an aging population, a heavy foreign debt load, and economic hardship amid the global downturn, Raúl Castro began liberalizing Cuba’s state-controlled economy in 2009. His reforms included decentralizing the agricultural sector, relaxing restrictions on small businesses, opening up real estate markets, allowing Cubans to travel abroad more freely, and expanding access to consumer goods. Cuba’s private sector swelled as a result, and the number of self-employed workers nearly tripled between 2009 and 2013.
Obama and Raúl Castro surprised the world in late 2014 by announcing that their governments would restore full diplomatic ties and begin to ease more than fifty years of bilateral tensions. The historic moment marked the culmination of eighteen months of secret diplomacy brokered by Pope Francis, during which the parties agreed to an exchange of prisoners, including Cuban intelligence officers and an American contractor, among other concessions.
Daily News BriefThe thaw continued in the years that followed. The Obama administration further loosened restrictions on remittances and travel, as well as on trade, telecommunications, and financial services. It also removed Cuba’s designation as a terrorism sponsor, a major obstacle to normalization. The two governments reopened their embassies—a move that was met with widespread public support in both countries—and negotiated a spate of bilateral agreements [PDF].
In early 2016, Obama took another significant step toward normalization, visiting Havana in what was the first trip to Cuba by a sitting U.S. president since Calvin Coolidge in 1928. In a keynote address broadcast live, with Raúl Castro sitting in the audience, Obama urged both countries to press on with reforms. The Cuban government should continue political and economic liberalization, and the U.S. Congress should lift the trade embargo, he said. Later that year, U.S. commercial airlines began offering service between the countries for the first time in more than fifty years.
Days before leaving office in January 2017, Obama repealed the Clinton-era “wet-foot, dry-foot policy” [PDF], which allowed Cubans who came to the United States illegally to pursue permanent residency. The move, which the Cuban government welcomed, brought the U.S. government’s treatment of Cubans in line with its handling of other unauthorized immigrants.
The death of Fidel Castro and the election of Donald Trump in 2016 rekindled debates over U.S.-Cuba policy. While in office, Trump followed through on campaign pledges to reverse course on much of the Obama administration’s thaw with Cuba.
In 2017, the Trump administration prohibited commerce with businesses controlled by or operating on behalf of the Cuban military, intelligence agencies, and security services. It also banned Americans from traveling to Cuba individually for educational and cultural exchanges. Months later, the administration said it would pull most of its embassy staff from Havana after American and Canadian diplomatic workers suffered unexplained injuries, including hearing loss and cognitive impairment, which later became known as “Havana Syndrome.” Many of the U.S. embassy’s functions, including the processing of most visas, were suspended. The Cuban government denied involvement in the mysterious attacks and urged the United States not to cut diplomatic ties. (The U.S. National Academies of Sciences, Engineering, and Medicine found that directed, pulsed radio-frequency energy was the most plausible explanation for the injuries among those it considered.)
Washington turned up its pressure on Havana in 2019, when it began allowing U.S. nationals to sue entities that traffic in or benefit from property confiscated by the Cuban regime. Congress provided for this in the Helms-Burton Act, but past U.S. presidents had routinely waived the provision. Canada and the European Union, both major foreign investors in Cuba, condemned the move as a violation of international law and pledged to protect their companies by fighting the decision through the World Trade Organization.
In addition to ending almost all individual travel to the island, Trump banned group educational exchanges in 2019. His administration prohibited cruise ships and other vessels from sailing between the United States and Cuba, banned U.S. flights to Cuban cities other than Havana, suspended private charter flights to Havana, and barred U.S. travelers from staying at hundreds of establishments linked to the Cuban government or Communist Party. (Americans have long sidestepped travel restrictions by flying to Cuba through other countries, including Mexico.) Administration officials framed the travel bans as an effort to keep tourism dollars out of Cuban government coffers. The White House further targeted Cuba’s finances by curbing remittances and imposing economic sanctions. In 2018, the United Nations estimated that U.S. trade restrictions had cost Cuba more than $130 billion since the embargo began. That same year, Raúl Castro’s hand-picked successor, Miguel Díaz-Canel, took office as president.
Meanwhile, the Trump administration grew increasingly wary of Cuba’s close ties with the embattled socialist regime in Venezuela. In 2018, National Security Advisor John Bolton characterized Cuba, Nicaragua, and Venezuela as a “troika of tyranny,” blaming their governments for massive human suffering and regional instability. The Trump administration sought to staunch the flow of oil from Venezuela to Cuba by sanctioning shipping firms and Cuba’s state oil company. It also banned Cuban officials from entering the United States for their alleged complicity in Venezuela’s human rights abuses and, as one of Trump’s final acts, redesignated Cuba as a state sponsor of terrorism, reversing the Obama administration’s 2015 determination.
As a candidate, Joe Biden pledged to reverse Trump’s policies on Cuba, which he said did not advance human rights and democracy. After taking office, the Biden administration said it hoped to eventually lift remittance restrictions and enable Americans to travel to Cuba, and it began a review of other Trump administration actions. It also appointed a high-level official to oversee the State Department’s response to the unexplained injuries U.S. diplomats sustained in Cuba. (U.S. intelligence agencies concluded in 2023 that the injuries were not likely to be caused by a foreign adversary, though some politicians are calling for a renewed assessment.) At the same time, Havana made some economic reforms, including easing restrictions on private businesses and unifying its dual currencies. It also expressed openness to Cuban American investors. In April 2021, Díaz-Canel replaced Raúl Castro as the first secretary of the Communist Party, ending decades of leadership by the Castro family.
However, the prospects for rapprochement faced new hurdles following the July 2021 outbreak of nationwide protests, Cuba’s largest in nearly three decades. Demonstrators said they were reacting to worsening economic conditions, including power outages, shortages of food and medicine, and spiking inflation. Analysts attributed these woes to a combination of U.S. restrictions, government mismanagement, and a nearly 90 percent drop in foreign currency due to a pandemic-related collapse in tourism. Cuba’s leaders responded by blaming foreign provocateurs, arresting protest organizers, and clamping down on internet and social media access across the island.
Biden called on the regime to respect Cubans’ rights to protest and “freely determine their own future,” and his administration imposed new sanctions on several Cuban officials, including high-level members of the national police. In Congress, many Democrats argued that Washington should help ameliorate Cuba’s humanitarian crisis, while some influential policymakers, including Senator Marco Rubio (R-FL), pressed Biden [PDF] to expand Trump-era sanctions, bolster the island’s internet access, and warn Havana against encouraging mass migration to the United States. In May 2022, following its Cuba policy review, the White House announced a series of measures to ease restrictions on the island, including expanding U.S. flights into the country, reestablishing a family reunification program, and lifting the remittance cap for families. Some critics, including Senate Foreign Relations Committee Chair Bob Menendez (D-NJ), have argued that the new measures will not help foster democracy, but rather bolster the communist government.
Conditions on the island continue to deteriorate. In March 2024, hundreds of demonstrators took to the streets to decry mass power outages and food shortages. Unlike with the 2021 demonstrations, the government responded to this unrest by ramping up electricity generation and distributing subsidized food rations, some of which China supplied. Havana also reiterated its accusations that Washington was stoking public dissent with the aim of overthrowing the communist-run government, which the White House denied.
Meanwhile, Cuba’s increasingly bleak economic situation has resulted in what experts say is the island’s largest wave of emigration in modern history. Since fiscal year 2021, U.S. border officials have encountered nearly five hundred thousand Cubans at the southern U.S. border. In an effort to manage irregular migration, the Biden administration announced in January 2023 that up to thirty thousand Cubans would be eligible for entry into the country each month as part of a humanitarian parole program; the program also applies to migrants from Haiti, Nicaragua, and Venezuela. However, that April, the administration restarted deportation flights to Cuba after a two-year pause.
