After over fifty years of animosity, U.S.-Cuba relations are undergoing a period of change. This shift follows decades of political and economic conflict, which have shaped a complex and often adversarial relationship. However, the history between the two nations, marked by periods of cooperation, offers hope for future reconciliation.
Early Economic and Political Ties
The roots of U.S.-Cuba relations stretch back to the colonial era, long before the Cuban Revolution. In 1776, Spain opened Cuban ports to North American merchants, establishing early trade ties. By the 19th century, Cuba’s sugar industry had become vital to the U.S., making Cuba an essential part of the American economic sphere.
During the Cuban War of Independence (1895-1898), the U.S. grew increasingly involved, partly due to the economic interests of American businesses in Cuba. In 1898, the explosion of the USS Maine in Havana Harbor led to U.S. intervention in the Spanish-American War. This action resulted in the defeat of Spain and marked the beginning of U.S. influence on the island.
Early 20th Century: U.S. Dominance and Cuban Resistance
Following the Spanish-American War, the U.S. exerted control over Cuba, first through military occupation and later via the Platt Amendment (1901), which allowed U.S. intervention in Cuban affairs and granted a naval base at Guantánamo Bay. Cuban sovereignty was significantly limited, and American businesses, particularly in sugar and tobacco, expanded their holdings.
By the 1920s, Cuba had become a popular tourist destination for Americans, especially during Prohibition, when Cuban liquor was a major draw. The U.S. also played a role in the rise of Fulgencio Batista, who came to power through a 1933 military coup with U.S. backing. Under Batista, Cuba became a playground for U.S. mobsters, but the corruption and inequality that grew under his rule sparked unrest.
The Cuban Revolution: Break from the U.S.
In 1959, Fidel Castro and his revolutionary forces overthrew Batista, fundamentally altering U.S.-Cuba relations. Castro’s government swiftly moved to nationalize U.S.-owned businesses and align Cuba with the Soviet Union. These actions led the U.S. to sever diplomatic ties and impose an economic embargo in 1960. Castro’s ideology and policies, which focused on anti-imperialism and nationalism, made him a figure of defiance against U.S. influence.
The U.S. responded with covert operations, including the infamous Bay of Pigs invasion in 1961, an unsuccessful attempt by CIA-backed Cuban exiles to overthrow Castro. A year later, the Cuban Missile Crisis brought the two countries to the brink of nuclear war when the Soviet Union placed nuclear missiles in Cuba. The crisis ended with a negotiated withdrawal of the missiles, but the confrontation left a lasting impact on U.S.-Cuba relations.
Cold War Tensions and Exile
For the next several decades, U.S. policy toward Cuba was shaped by the Cold War. Cuba’s alignment with the Soviet Union made it a target for U.S. hostility. Cuban exiles, particularly those in Florida, became a powerful lobby against Castro, pushing for U.S. policies that sought to destabilize his regime. This included support for anti-Castro groups and a strict enforcement of the embargo, which limited U.S. interactions with the island.
The 1980 Mariel Boatlift, when over 100,000 Cubans fled to the U.S., highlighted the ongoing tension between the two countries. Despite humanitarian crises and calls for reform, the U.S. continued to isolate Cuba diplomatically and economically. In the 1990s, after the collapse of the Soviet Union, Cuba faced a severe economic crisis, but the embargo remained intact, contributing to widespread hardship.
The Clinton Era: A Brief Relaxation
The 1990s brought a slight shift. In 1994, following a mass exodus of Cuban refugees, the U.S. and Cuba reached an agreement to limit the number of refugees allowed to enter the U.S. In 1999, the case of Elián González, a young boy rescued after a boat accident, became a flashpoint in U.S.-Cuba relations. After a highly publicized custody battle, Elián was returned to Cuba, marking a rare moment of cooperation.
Despite these isolated instances of engagement, the embargo and diplomatic tensions remained firmly in place throughout the 1990s and 2000s. In the early 2000s, the U.S. increased its support for dissident groups in Cuba, and in 2003, the Cuban government jailed dozens of opposition figures, many of whom had ties to U.S. organizations.
The Obama Thaw: A New Beginning
The most significant shift in U.S.-Cuba relations came in the 2010s. President Barack Obama, seeking to end decades of isolation, took bold steps toward normalizing ties. In 2009, he eased travel restrictions for Cuban Americans and allowed more remittances to be sent to Cuba. The breakthrough came in 2014 when the U.S. and Cuba agreed to swap prisoners, releasing the “Cuban Five” (Cuban spies imprisoned in the U.S.) and Alan Gross, a U.S. contractor imprisoned in Cuba. This move paved the way for further diplomatic engagement.
In 2015, the U.S. and Cuba reopened embassies in each other’s capitals, marking the first time in over fifty years that American and Cuban diplomats were stationed in each other’s countries. The same year, President Obama visited Cuba, becoming the first sitting U.S. president to do so since 1928. This visit, combined with the re-establishment of trade and travel links, signaled the start of a new era in relations.
Obama’s administration also made significant moves to ease the embargo. Cuban companies were allowed to engage in limited trade with U.S. businesses, and American companies like Google and Airbnb began to invest in the Cuban market. Travel restrictions were relaxed, allowing Americans to visit Cuba more easily for educational and cultural exchanges.
The Trump Reversal: Setbacks in Diplomacy
Despite the progress made under Obama, President Donald Trump reversed many of the changes implemented by his predecessor. In 2017, he reinstated restrictions on business dealings and travel, particularly aimed at targeting Cuba’s military and security sectors. These moves were popular among hardline Cuban-American voters in Florida, a key electoral group, and reflected Trump’s broader foreign policy approach, which focused on reversing what he perceived as Obama’s concessions to authoritarian regimes.
Trump’s policies effectively stalled the momentum toward normalization, although the U.S. embassy remained open in Havana. By 2020, relations had significantly cooled again, as Cuba faced its own internal economic struggles and growing political repression, including the crackdown on the 2021 protests.
The Future of U.S.-Cuba Relations
As of 2025, U.S.-Cuba relations remain in flux, with the Biden administration adopting a cautious stance. Biden has expressed interest in continuing dialogue and restoring some of the Obama-era policies, particularly those affecting Cuban American families. However, the full lifting of the embargo remains unlikely due to the influence of Cuban-American political groups, especially in Florida, as well as the broader geopolitical climate.
Cuba, for its part, continues to struggle with internal economic reforms, political dissent, and the aftermath of the COVID-19 pandemic. While the government has made some attempts to open up the economy, including allowing small businesses and foreign investment, the country remains tightly controlled by the Communist Party. Political repression and human rights issues remain major sticking points for the U.S., preventing a more comprehensive normalization of relations.