U.S.-Cuba Relations

President Trump has unleashed new trade and travel restrictions on Cuba, closing out a historic period of détente between the two longtime adversaries.
A man shows U.S. and Cuban flags at his house in Havana.
A man shows U.S. and Cuban flags at his house in Havana. Yamil Lage/AFP/Getty Images
  • The United States and Cuba have had a strained relationship for more than sixty years, rooted in Fidel Castro’s overthrow of a U.S.-backed government.
  • Presidents Barack Obama and Raul Castro took several steps to normalize bilateral relations, including restoring diplomatic ties and expanding travel and trade.
  • The Trump administration has reversed aspects of the détente by reimposing restrictions on tourism and other commerce.

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.

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President Barack Obama took some extraordinary steps to normalize U.S. relations with Cuba, meeting with leader Raul Castro and restoring full diplomatic ties. However, President Donald J. Trump’s administration has largely reversed course, imposing a raft of new sanctions and labeling Cuba, along with Venezuela and Nicaragua, part of the “Troika of Tyranny.”

What triggered the falling out between Washington and Havana?

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Raul Castro

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.

What was the Cuban Missile Crisis?

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.   

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How did relations evolve over the rest of the Cold War?

In 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 Central America and Africa. Both Presidents George H.W. Bush and Bill Clinton signed laws—the Cuba Democracy Act of 1992 [PDF] and the Cuban Liberty and Democratic Solidarity Act of 1996 [PDF]—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. 

Some adjustments in 1999 allowed for the export of U.S.-made medical supplies and food products to the island. Restrictions tightened, however, under President George W. Bush, whose Commission for Assistance to a Free Cuba increased enforcement of existing sanctions.

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How did U.S.-Cuba relations normalize?

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 openness to reform under the new leadership of Fidel’s brother, Raul. Facing an aging population, a heavy foreign debt load, and economic hardship amid the global downturn, Raul Castro began liberalizing Cuba’s state-controlled economy in 2009. 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 [PDF] between 2009 and 2013.

Obama and Raul 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 in which the parties agreed to an exchange of prisoners, including Cuban intelligence officers and an American development contractor, among other concessions.

The thaw continued in the years that followed. The Obama administration further loosened restrictions on remittances and travel, as well as 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 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 Raul 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 brought the U.S. government’s treatment of Cubans in line with its handling of other unauthorized immigrants.

What policy changes has President Trump made?

The death of Fidel Castro and the election of Donald J. Trump in 2016 rekindled debates over U.S.-Cuba policy. As a candidate, Trump was fiercely critical of the Obama administration’s thaw with Cuba and he pledged to reverse course once in office. Despite maintaining diplomatic relations, Trump has largely delivered on his promise through policies that curtail trade and tourism, and target Havana’s purse strings. At the same time, the Trump administration has criticized the Cuban government for its poor human rights record and Communist-dominated politics.

In a 2017 memorandum [PDF], Trump announced prohibitions on commerce with businesses owned by the Cuban military and security services, and placed a ban on individual travel to Cuba 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. Many of the U.S. embassy’s functions, including most visa processing, have been suspended. The Cuban government denied involvement and urged the United States not to cut diplomatic ties. (U.S. investigators have not determined the source of the attacks.)   

Washington turned up 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 1996 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 notably banned group educational exchanges in 2019. He prohibited cruise ships and other vessels from sailing between the United States and Cuba, and forbid U.S. flights to Cuban cities other than Havana. (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 has further targeted Cuba’s finances by curbing family remittances and imposing economic sanctions. In 2018, the United Nations estimated U.S. trade restrictions had cost Cuba more than $130 billion since the embargo began. That same year, Raul Castro’s handpicked successor, Miguel Diaz-Canel, took office.

Meanwhile, the Trump administration has grown 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 these governments for massive human suffering and regional instability. The Trump administration has sought to staunch the flow of oil from Venezuela to Cuba by sanctioning shipping firms and Cuba’s state oil company. It has also banned Cuban officials from entering the United States for their alleged complicity in Venezuela’s human rights abuses.

Recommended Resources

The Congressional Research Service explains how the Trump administration has reshaped U.S. policy toward Cuba [PDF].

Marguerite Jimenez argues in Foreign Affairs that the Trump administration should reach out to Diaz-Canel.

Michael Bustamante looks at the consequences of Trump’s rollback on Cuba in Foreign Affairs.

In her book Cuba: What Everyone Needs to Know, Julia Sweig offers a guide to the island’s politics, its relationship with the United States, and its shifting role in the world.

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