Since Fidel Castro’s ascent to power in 1959, U.S.-Cuba ties have endured a nuclear crisis, a long U.S. economic embargo, and persistent political hostilities. The diplomatic relationship thawed under President Barack Obama, but many restrictions have since been renewed.
Fidel Castro establishes a revolutionary socialist state in Cuba after he and a group of guerrilla fighters successfully revolt against President Fulgencio Batista. Batista, who had been supported by the U.S. government for his anticommunist stance, flees the country after seven years of dictatorial rule. Castro gradually strengthens relations with the Soviet Union.
Castro nationalizes all foreign assets in Cuba, hikes taxes on U.S. imports, and establishes trade deals with the Soviet Union. President Dwight D. Eisenhower retaliates by slashing the import quota for Cuban sugar, freezing Cuban assets in the United States, imposing a near-full trade embargo, and cutting off diplomatic ties with the Castro government.
Executing a plan developed and approved by the Eisenhower administration, President John F. Kennedy deploys a brigade of 1,400 CIA-sponsored Cuban exiles to overthrow Fidel Castro. The Cuban military defeats the force within three days, after several mishaps disadvantage the invaders and reveal U.S. involvement. Despite the failed invasion, U.S. administrations over the next several decades conduct covert operations against Cuba.
The Kennedy administration imposes an embargo on Cuba that prohibits all trade. Cuba, whose economy greatly depended on trade with the United States, loses approximately $130 billion over the next nearly sixty years, according to Cuban government and United Nations estimates.
U.S. spy satellites discover that Cuba has allowed the Soviet Union to build nuclear missile bases on the island. In response, Kennedy demands the Soviet weapons be removed and orders a naval quarantine of Cuba, igniting a thirteen-day standoff. With the threat of nuclear war on the horizon, the United States negotiates with the USSR via back channels. As the crisis nears its third week, Kennedy secretly agrees to withdraw U.S. nuclear missiles from Turkey within a few months if the Soviet Union withdraws its missiles from Cuba. Kennedy also pledges not to invade Cuba. Soviet Premier Nikita Khrushchev accepts the deal and announces that he will order the missiles removed. The following July, Kennedy prohibits U.S. nationals from traveling to Cuba.
Castro indicates in a September 1965 speech that Cubans can leave for the United States of their own free will, saying that “nobody who wants to go need go by stealth.” Days later, President Lyndon B. Johnson announces he will open U.S. borders to all Cubans and signs into law an immigration bill that gives preference to Cuban migrants with family ties to U.S. citizens or residents. The U.S. State Department estimates that some 270,000 Cubans have arrived in the United States since Castro took power. In November 1966, Johnson enacts a law that allows Cubans who reach the United States to pursue permanent residency after one year.
President Jimmy Carter reaches an agreement with Castro to resume a limited diplomatic exchange, allowing officials from the two countries to communicate regularly. The United States opens an interests section with a small staff in its former embassy in Havana under the auspices of the Swiss embassy. Switzerland had taken over U.S. interests in Cuba in 1961. Meanwhile, Cuba opens an interests section in Washington, DC, under the auspices of the embassy of Czechoslovakia.
Cuba faces intense pressure from thousands of Cubans hoping to flee the country as its economy suffers from a spike in oil prices and the continued U.S. embargo. Following a forty-eight-hour debacle in which ten thousand Cubans crowded at the gates of the Peruvian embassy to gain asylum, Castro states that anyone wishing to leave Cuba for Florida may do so from Mariel Harbor over the next six months. President Carter welcomes Cubans to the United States “with open arms,” and as many as 125,000 Cubans take part in the boatlift.
President Ronald Reagan designates Cuba a state sponsor of terrorism, censuring the Castro government for providing support to militant communist groups in African and Latin American countries including Angola, El Salvador, Guatemala, and Nicaragua. Cuba maintains that “acts by legitimate national liberation movements cannot be defined as terrorism,” according to a U.S. State Department report. Due to the heavy economic sanctions already in place, the designation is largely a symbolic act.
Radio Martí begins broadcasting news and entertainment programming to Cuba from studios in the United States. The federally funded station was proposed by Reagan in 1981 and created by Congress two years later. The Cuban government condemns the service as U.S. propaganda, jams the new station’s broadcasts, and calls its use of independence hero José Martí’s name a “gross insult.” Castro suspends an immigration agreement that would have allowed up to twenty thousand Cubans a year to immigrate to the United States and provided for the repatriation of some three thousand Cubans with criminal records or who suffer from mental illness. Cuba also halts visits by Cubans living in the United States.
President George H.W. Bush signs the Cuban Democracy Act, which increases U.S. economic sanctions on Cuba. The move follows the Soviet Union’s 1991 collapse, with Bush stating that Cuba’s “special relationship with the former Soviet Union has all but ended. And we’ve worked to ensure that no other government helps this, the cruelest of regimes.” The statute bars vessels that have exchanged goods with Cuba in the previous 180 days from docking at U.S. ports and prohibits foreign subsidiaries of U.S. businesses from trading with Cuba. The legislation also limits the amount of U.S. currency traded with Cuba. The act does, however, offer a path to normalizing relations that is conditioned on Castro’s government making significant economic and political reforms.
Havana and Washington implement two accords aimed at addressing the thousands of Cubans attempting to enter the United States annually. The first follows an abrupt policy change by President Bill Clinton in August 1994 that calls for all Cubans rescued at sea to be brought to the U.S. naval base at Guantánamo Bay. It outlines terms for future legal immigration from Cuba to the United States, setting the number of Cubans allowed to enter the U.S. annually at a minimum of twenty thousand (not including immediate relatives of U.S. citizens). The second accord establishes the “wet foot, dry foot” policy [PDF], in which Cubans intercepted by U.S. authorities at sea are sent home while those who make landfall in the United States are allowed to remain and pursue permanent residency after one year. The agreement also allows for more than thirty thousand Cubans detained at Guantánamo Bay to enter the United States on parole status.
Clinton signs the Cuban Liberty and Democratic Solidarity Act, better known as the Helms-Burton Act, which tightens and codifies the U.S. embargo. It comes several weeks after the Cuban military shot down two U.S. civilian planes over waters off of Florida. Among other provisions, the statute penalizes foreign companies that do business with Cuba, provoking some U.S. allies to denounce it as a violation of international law. The law stipulates that sanctions may only be lifted after Fidel Castro and his brother Raúl are no longer in office, Cuba has moved toward free elections and a free press, and it has released political prisoners.
The Clinton administration charges five Cuban counterintelligence officers in the United States with conspiracy to commit espionage, among other illegal activities. The officers, who were sent by the Castro government to infiltrate Cuban-American exile groups in Miami, are arrested in 1998 and found guilty in 2001. Two are released at the end of their terms, in 2011 and 2014, and the remaining three are released on December 17, 2014, as part of a prisoner swap for a U.S. intelligence officer held in Cuba.
The case of five-year-old Elián González, the sole survivor of an attempt by his mother and ten others to reach the United States by boat, ignites a media storm. The Clinton administration is faced with deciding whether to allow the child’s Miami relatives to keep him, the course of action supported by Florida’s Cuban-American community, or send him back to his father in Cuba, the position of the Cuban government. After a seven-month battle in U.S. courts, a federal appellate court gives Elián’s father the power to act on his behalf in immigration proceedings. After the U.S. Supreme Court declines to review the case, Elián is returned to his family in Cuba.
Venezuelan President Hugo Chávez signs an agreement with Castro allowing Venezuela to send oil to Cuba at a heavy discount in return for Cuban support in education, health care, science, and technology. Chávez aligned himself early on with Castro’s anti-U.S. stance and, soon after taking office in February 1999, announced a government overhaul of state oil giant PDVSA, the largest foreign supplier of oil to the United States at the time. In the following years, Venezuela boosts its oil exports to Cuba in return for more technical personnel from Cuba, including physicians, teachers, and other social-service workers.
Fidel Castro, announcing that due to his declining health he can no longer serve as president of Cuba, hands over the presidency to his brother, Raúl, who had served as second-in-command of the government and a general in the armed forces. Fidel had already transferred power to Raúl in 2006, when an illness forced Fidel to undergo surgery (he still remained active in government affairs). In response to Fidel’s resignation, President George W. Bush says Cuba should embrace democracy, adding that “the United States will help the people of Cuba realize the blessings of liberty.” While campaigning for the U.S. presidency in 2008, Democratic nominee Barack Obama says, “If the Cuban leadership begins opening Cuba to meaningful democratic change, the United States must be prepared to begin taking steps to normalize relations and to ease the embargo of the last five decades.”
President Obama eases restrictions on travel and remittances, which had been tightened by his predecessor. The move allows Cuban-Americans to send unlimited funds to Cuba and permits U.S. citizens to travel there for religious and educational purposes. The step is widely considered the most notable move yet toward normalizing relations, though the trade embargo remains in place.
Alan Gross, a subcontractor working on a democracy-promotion program for the U.S. Agency for International Development, is arrested in Cuba. Gross was bringing technology to help Cuba’s Jewish community gain access to the internet, which is heavily restricted on the island. Havana considers the U.S. agency’s activities subversive and illegal, and in 2011, Gross is convicted of attempting to “undermine the integrity and independence” of Cuba and sentenced to fifteen years in prison.
The Cuban government approves a slew of economic reforms in May 2011, allowing citizens to buy and sell residential real estate and automobiles, increasing bank lending, and expanding self-employment.
Cuba hosts for the first time the Community of Latin American and Caribbean States (CELAC) summit, during which regional leaders discuss trade, peace, and human rights. CELAC is considered an alternative to the U.S.-dominated Organization of American States (OAS), from which Cuba was ousted in 1962. Cuba’s OAS rights were restored in June 2009, but the Cuban government said it would not return to the institution, calling it “an organization with a role and a trajectory that Cuba repudiates.”
Barack Obama and Raúl Castro announce they will restore full diplomatic ties following the exchange of a jailed U.S. intelligence officer for the three remaining Cuban Five prisoners. Gross is also released. The prisoner swap and release of Gross comes after nearly eighteen months of secret talks between U.S. and Cuban officials that were brokered, in part, by Pope Francis. Obama says the United States plans to reopen the embassy in Havana, while members of the Republican-controlled Congress condemn the move and vow to uphold the economic embargo.
The U.S. State Department removes Cuba from its list of state sponsors of terrorism. The designation, first imposed in 1982, had prevented Cuba from accessing international finance and was a sticking point in U.S.-Cuba talks on normalizing relations. Obama had called for Cuba’s removal from the list in April, after the State Department found that Cuba had not sponsored terrorism in recent years and vowed not to do so in the future. Obama's announcement came days after he met with Raúl Castro on the sidelines of the Summit of the Americas in the first face-to-face discussion between U.S. and Cuban heads of state in more than half a century.
The United States and Cuban embassies, which had been closed since 1961, reopen. The U.S. trade embargo, which cannot be lifted without congressional approval, remains in place, however, and neither country names an ambassador. The top U.S. diplomat stationed in Havana is the charge d’affaires, Jeffrey DeLaurentis, while Cuba’s foreign minister, Bruno Rodríguez Parrilla, oversees the reopening of Havana’s embassy in Washington.
Obama becomes the first sitting U.S. president in nearly ninety years to visit the island nation. Obama meets with Raúl Castro, as well as dissidents. His trip comes a month after Cuba and the United States signed an agreement to allow commercial flights between the two countries for the first time in more than fifty years. The first passenger jet flight takes place in August, and in the weeks that follow, several U.S. airlines begin service to Cuba.
Fidel Castro dies at the age of ninety. Hundreds of thousands of Cubans gather at Havana’s Revolution Square to mark the first day of an official week of mourning. The country’s most prominent dissident group, Ladies in White, calls off its regular weekend protest for the first time in thirteen years. Thousands of Cuban exiles, many of whom regarded Castro as a dictator, celebrate in Miami and other U.S. cities and call for political change in Cuba. In a statement, Obama says that Cubans should know “they have a friend and partner in the United States of America.”
President Donald Trump announces that he will reinstate restrictions on Americans traveling to Cuba and U.S. business dealings with a military-run conglomerate but will not break diplomatic relations. The Obama administration’s loosened restrictions “do not help the Cuban people—they only enrich the Cuban regime,” Trump says, adding that U.S. sanctions will not be lifted until Cuba frees all of its political prisoners, respects freedoms of assembly and expression, legalizes opposition parties, and schedules free and fair elections. Some U.S. business leaders and members of Congress criticize the move, saying it will further isolate Cuba and worsen the economic and political situation there. Cuban leaders say the changes “contradict the majority support” of Americans. The policy leaves in place new direct flights from the United States, cruise ship routes, and hotel ventures.
The State Department announces it will withdraw most staff from the U.S. Embassy in Havana after diplomats and intelligence personnel develop mysterious health problems, including hearing loss and dizziness. Days later, it expels fifteen Cuban diplomats from the United States for failing to protect Americans in Havana. The illness, first reported in 2016, prompts speculation about a targeted attack by the Cuban government. Cuba, however, denies harming U.S. personnel and denounces the State Department’s actions. The country’s foreign minister later alleges the situation is a “pretext” for the Trump administration’s backtracking on U.S.-Cuba normalization.
The National Assembly unanimously elects fifty-seven-year-old Miguel Díaz-Canel Bermúdez, first vice president and Castro’s hand-picked successor, as president of Cuba. Castro says he will remain the head of the Communist Party until 2021, a move that preserves his political influence. The transition marks the first time in more than forty years that a Castro is not the island’s president.
In a high-profile address on U.S. policy in Latin America, National Security Advisor John Bolton labels Cuba, Nicaragua, and Venezuela the “Troika of Tyranny,” blaming the trio for human rights abuses, causing regional instability, and embracing communism. Bolton’s speech marks a turning point in the Trump administration’s policy toward the island, and it soon announces a wave of sanctions designed to penalize Cuba and weaken its ties to Venezuela. Most notably, Trump permits certain lawsuits against companies that benefit from property confiscated by Cuba’s government. He also further restricts travel to Cuba, prohibiting group educational trips, banning cruises, and curtailing direct flights. Despite U.S. pressure, Cuba remains one of Venezuela’s closest allies.
The U.S. State Department returns Cuba to its list of state sponsors of terrorism, reversing another Obama-era step toward normalization, as Trump prepares to leave office. Secretary of State Mike Pompeo cites Cuba’s harboring of U.S. fugitives and Colombian rebels, as well as its support for Venezuela’s regime. But some experts question the administration’s motives, viewing the designation as a reward for Trump’s supporters, particularly Cuban-Americans. Cuban officials decry the move as “political opportunism” and accuse Washington of long-standing terrorism against Havana. The redesignation carries sanctions, though existing U.S. restrictions on Cuba are expected to blunt their effects.
Díaz-Canel is elected first secretary of the Communist Party, Cuba’s most powerful political position, replacing Raúl Castro and ending more than six decades of rule by either Fidel or Raúl Castro. The transfer of power occurs during a party congress that coincides with the sixtieth anniversary of Cuba defeating U.S.-backed forces in the Bay of Pigs invasion. Díaz-Canel takes over amid steep economic challenges, growing calls for domestic reform, and uncertainty about relations with the United States under the Joe Biden administration. In response to Castro’s resignation, the White House says shifting U.S. policy toward Cuba is not one of Biden’s highest foreign policy concerns.
Tens of thousands of Cubans take to the streets—the country’s largest demonstrations in nearly three decades—to protest worsening economic conditions amid the COVID-19 pandemic. Their complaints are over power outages, shortages of food and medicine, and spiking inflation. Havana responds by blaming foreign provocateurs, arresting hundreds of protesters, and clamping down on internet and social media access. Biden calls on the Díaz-Canel administration to respect Cubans’ right to protest, and he imposes new sanctions on several officials accused of human rights violations, including high-level members of the national police.
The White House lifts some restrictions on the island, including by expanding U.S. flights into the country, reestablishing a family reunification program, increasing visa processing, and lifting the remittance cap for families. It says the changes seek to “further support the Cuban people, providing them additional tools to pursue a life free from Cuban government oppression and to seek greater economic opportunities.” Some critics, including Senate Foreign Relations Committee Chair Bob Menendez (D-NJ), argue that the new measures will instead bolster the communist government. The shift comes even as Washington excludes Havana from the Summit of the Americas in Los Angeles the following month, a move opposed by Mexico and other countries in the region.
The Biden administration sends more than one hundred Cuban nationals back to Cuba in the first deportation flight to the island since the onset of the pandemic. The decision comes after a record number of Cubans, nearly 221,000, arrived at the southern U.S. border in fiscal year 2022. Despite a new humanitarian parole program for nationals of Cuba and three other Latin American countries, illegal border crossings continue to rise dramatically. They are expected to increase further after Title 42, a policy that denies asylum on pandemic-related grounds, ends in mid-May. Cuba remains embroiled in a severe economic crisis that has seen soaring inflation raise food prices and other costs under the leadership of Díaz-Canel, who begins a second five-year term this month.