The United States and Cuba share a long, complex history—first as allies and trade partners, and later as bitter ideological enemies.

For four centuries after the arrival of Christopher Columbus, Spain ruled Cuba as its main colony in the Caribbean, but the U.S. long coveted the island just off its southern coast. America provided major markets for Cuba’s sugar, tobacco, rice and coffee exports, while the island played a key role in the transatlantic trade in enslaved Africans.

After America helped Cuba break free from Spanish rule in 1898, the U.S. government continued to intervene militarily and American businesses continued to invest economically, while U.S. mobsters made the island their money-laundering playground. But after the Cuban revolution installed the Western hemisphere’s most stringent socialist regime in 1959 and nationalized U.S.-owned businesses, relations quickly frayed. Even after the Cold War ended, the clash of capitalist and socialist ideologies continued.

This timeline shows how closely entwined America and Cuba have been over the last two centuries.

1818: Spain opens Cuban ports for international trade, helping make America the island’s principal trading partner.

1854: **The U.S. government’s Ostend Manifesto—**a secret plan to buy Cuba from Spain for $130 million—fails when anti-slavery campaigners expose the scandal.

1868-78: The Ten Years War. While America’s government remains officially neutral to Cuba’s first rebellion against Spain, U.S.-based sympathizers smuggle men, money and munitions to the rebels. During the turmoil, U.S. investors buy large tracts of land at low prices and thousands of Cubans emigrate to America. According to U.S. State Department records, by the end of the war, Americans purchase almost all of Cuba’s exports and by 1895, do more than $100 million a year in trade.

1898: The Spanish-American War. In February, the USS Maine mysteriously explodes in Havana Harbor, killing more than 250 American sailors. The tragedy fuels calls for America to liberate Cuba militarily and protect U.S. business interests there. Fighting starts in April. By December, Spain has surrendered, ceding Cuba, Puerto Rico and the Philippines to the U.S. in the Treaty of Paris.

1901-02: Military control. America enacts the Platt Amendment, consenting to withdraw troops from Cuba once the island territory agrees that the U.S. has an ongoing right to intervene militarily to protect strategic and business interests. It also leases land at the southern portion of Guantanamo Bay to build a naval base.

1902: Cuban Republic. U.S. ceases military occupation of Cuba and establishes diplomatic relations, effectively launching the Republic of Cuba.

1933: Military coup. After the American military quashes three Cuban uprisings in as many decades, the U.S. backs a military coup led by Sgt. Fulgencio Batista. Whether as president or as a strongman behind other presidents, Batista takes control.

1952: Batista grabs power. Deposing President Carlos Prio Socarras, Batista abandons the constitution and halts elections, continuing his corrupt rule that favors U.S. interests and Cuban aristocrats while leaving the poor destitute. One year later, Fidel Castro stages a failed coup.

1920s-1958: American economic dominance. Americans in the Prohibition era swarm to casinos and lavish hotels in Havana. U.S. corporations thrive during the Batista years as organized crime figures find a welcoming and safe “playground” to grow illegal businesses. American tourism to Cuba flourishes.

1959: Cuba’s Revolution triumphs. Six years of guerrilla warfare against the dictatorship ends when Batista, no longer getting weapons from the U.S., flees Havana on New Year’s Eve 1958. The U.S. recognizes Cuba’s new government a week later. Rebel leader Fidel Castro becomes prime minister within a month.

1960-61: Hostilities begin. Cuba nationalizes all U.S. businesses—with no financial redress. The U.S. severs diplomatic ties with the new regime, imposing a partial trade embargo. Cuba turns to a new trading partner, the Soviet Union.

1961: Bay of Pigs Invasion. According to CIA internal documents, a battalion of about 1,500 CIA-trained Cuban exiles fail in an invasion at Cuba’s Bay of Pigs (Playa Girón) and nearly 1,200 are taken prisoner. Castro uses the embarrassing botched invasion to call for the Cuban people to defend the revolution.

1959-62: Waves of exiles start. President John F. Kennedy establishes the Cuban Refugee Program in 1961. From the revolution to the final commercial flight between Havana and Miami in October 1962, nearly a quarter-million Cubans flee to the U.S., including some 14,000 unaccompanied Cuban children in Operation Pedro Pan.

1961: “Socialism or Death.” Castro proclaims Cuba a socialist state.

1962: Cuban Missile Crisis. After months of CIA-coordinated terrorist bombings, military sabotage and assassination attempts on Cuban leaders, tensions peak when U.S. reconnaissance planes take photos of Soviet forces building silos for intermediate-range missiles in Cuba. To end the standoff that has brought the world to the brink of nuclear war, the Soviets remove the missiles in Cuba in exchange for the American withdrawal of nuclear missiles from Turkey.

1965: Freedom Flights. With Castro’s blessing, about 3,000 Cubans leave for the U.S. during one month in the fall. That lays the groundwork for the “Freedom Flights” air bridge between Varadero and Miami, which brings more than a quarter-million more Cubans to the U.S. by the time its last flight lands in 1973.

1966: Permanent Residence. Congress greenlights the Cuban Adjustment Act, granting Cubans permanent residence in the U.S. under more favorable terms than other immigrant groups.

1977-78: Tensions Briefly Ease. Both countries establish limited diplomatic ties in 1977. Cuban government officials and 75 exiles meet in Havana in 1978 to negotiate family reunification, travel to Cuba and the release of political prisoners. More than 100,000 exiles visit Cuba the following year.

1980. Mariel Boatlift: About 10,000 Cubans seeking political asylum cram into the Peruvian embassy in Havana. Castro responds by stating that anyone who wants to leave Cuba can do so through the Port of Mariel. Some 125,000 people leave in what becomes known as the Mariel boatlift.

1984: Immigration agreement. Cuba accepts the return of 2,746 Mariel refugees with criminal records. The U.S. agrees to accept up to 20,000 Cuban immigrants annually.

1985: Radio Martí. During the Reagan administration’s hardline stance against communism, the U.S. begins broadcasting news and information to Cuba on the new Radio Marti, named after the Cuban national hero, poet and martyr José Martí. Cuba’s response? Canceling family visits and suspending the previous year’s immigration pact.

Early 1990s: Cuba’s “special period.” Soviet Union collapses. Without its economic patronage, so does the Cuban economy. Food shortages abound. The U.S. allows private aid groups to deliver food and medicine to Cuba. The Cuban government legalizes use of the U.S. dollar by Cubans, creating a dual-currency system that heightens inequality.

1992: Tighter sanctions. U.S. Congress hardens sanctions, prohibiting U.S. subsidiaries in other countries from conducting trade with Cuba.

1994: Rafter Crisis. To quell riots, boat hijackings and break-ins at ambassadors’ homes, Castro announces that all wishing to leave Cuba can do so. For five weeks starting August 13, some 31,000 desperate Cubans climb on makeshift “vessels” mostly made of doors, inner tubes and beams held together by cords. Thousands plucked from the open seas are held in tent cities on the U.S. Naval Station in Guantanamo Bay, with many allowed to enter the U.S. starting the following year. An estimated 16,000 to 100,000 Cubans die at sea. In September, the U.S. agrees to issue 20,000 visas a year for Cubans, and Cuba agrees to stop the exodus.

1995: Wet foot, dry foot policy: President Bill Clinton changes part of the longtime favorable immigration policy for Cubans: Those who reach U.S. soil could stay; those saved at sea would be taken back to Cuba or to a third country.

1996: Brothers to the Rescue. Cuba shoots down two small planes from the Brothers to the Rescue organization, killing four Cuban exiles planning to release anti-Castro pamphlets over Cuba. In response, President Clinton and Congress strengthen the embargo to block foreign companies from trading with Cuba and punish those who traffic in property confiscated during the revolution.

1998: Cuban Five. Five Cuban spies are arrested in the U.S. for infiltrating activist groups like Brothers to the Rescue. Cubans call for the “imperialist bully” to release them.

2000: Elián Gonzalez. The U.S. government forcibly removes 5-year-old Elián Gonzalez from his relatives’ home in Miami’s Little Havana to reunite him with his father in Cuba after a protracted international custody battle. Found drifting at sea in an inner tube, Elián is one of three who survived the voyage from Cuba on a ramshackle “vessel” where his mother died. The decision to return Elián to his father becomes an international controversy fueled by the Cuban exile community that vehemently fought his return to a regime so many had fled.

2009-13: The thaw begins. President Barack Obama lifts limits on remittances and U.S. restrictions on family travel, along with travel by U.S. citizens to Cuba for cultural and educational exchanges. The Cuban government liberalizes some travel restrictions and issues passports to dissidents to travel abroad.

2014: Prisoner swap. The last three of the “Cuban Five” spies still in jail in the U.S. are exchanged for a U.S. spy behind bars in Cuba.

2015: New embassies. Both countries restore diplomatic relations and open embassies.

2016: Presidential visit. President Obama travels to Havana, the first sitting president to visit Cuba since 1928. Commercial flights resume—the first between both countries since 1962. Upon leaving office, President Obama nixes the 20-year-old “wet foot, dry foot” policy regarding the arrival of Cuban refugees.

2017: New restrictions. President Donald Trump reverses some of Obama’s Cuban initiatives, restricting individual people-to-people travel, and prohibiting U.S. business transactions with Cuban institutions run by the military.

2017: Sonic attacks. State Department personnel at the embassy in Havana are ordered to leave Cuba after mysterious “sonic attacks” against 24 employees. The U.S. expels 15 diplomats from the Cuban embassy in Washington.

2019-20: More restrictions. Trump bans most commercial flights and cruise ships from traveling to Cuba. The U.S. blocks remittances to Cuba through companies controlled by the Cuban military. Western Union closes 407 money transfer stations on the island.

2021: A parting shot. Upon leaving office, Trump reinstates Cuba to the U.S. State Department’s list of state sponsors of terrorism, a move Obama had reversed as part of his thaw on Cuba relations.

2021: Taking to the streets. Thousands of Cubans protest lack of food, fuel, medicine and freedom in rare massive demonstrations throughout the island. The Biden administration expresses its support of the people’s right to peaceful demonstrations and criticizes Cuba’s violent crackdown on protesters.