Cuba in the Crosshairs

 

The relationship between the United States and Cuba is growing increasingly tense. On Wednesday, May 20th, 2026, the United States announced the unsealing of an indictment against Raúl Castro, the former President of Cuba, along with five other individuals allegedly responsible for the Feb. 24, 1996 shoot down of two unarmed U.S. civilian aircrafts operated by Brothers to the Rescue (BTTR). The indictment is the latest American salvo against Cuba and Raúl Castro; a man who played a key role in launching the Cuban Revolution that would elevate his brother, Fidel Castro, to Prime Minister of Cuba in 1959. This indictment marks a new era in the contentious history relations between the United States and Cuba, and signals that the Trump administration may attempt to bring about regime change in Cuba in the near future.

 

Cuba is at its weakest point in decades. Years of mismanagement and centralized planning under the absolute primacy of the country’s Communist Party has stunted Cuba’s socio-economic growth and has led to a dramatic diminishment in Cuba’s oil supply. The consequences of COVID-19 and tightened sanctions by the United States under President Trump have compounded the crisis. As a result, economic reform has completely stalled, leaving the country and its people desolate. Sky-high inflation, crumbling infrastructure, and limited access to medical care has generated vast discontent among the island nation. For Cuba and its people, there seem to be few options moving forward. Considering the legal precedent set by the indictment of Raúl Castro and the increasing tensions between the United States and Cuba, it is crucial to assess Cuba’s layered history against the backdrop of American interventionism under the second Trump administration to better assess where the country may go from here?

 

A Brief History of Cuba

 

Cuba’s recorded history began in 1492, when Christopher Columbus landed on the island during his first expedition to the New World and claimed the territory for Spain. Indigenous tribes had inhabited the island, known as Cubanacan and Caobana, for centuries prior to the arrival of Columbus. However by 1511, the island’s natives were conquered by Conquistador Diego Velázquez de Cuéllar, commencing nearly 400 years of Spanish rule. Velázquez would establish Spain’s first permanent colony in Baracoa and become Cuba’s first Governor.

 

Spain’s colonization of Cuba would mark the beginning of the tragic history of slavery in Cuba. Cuba’s first record of slavery was in 1513, with the first group of salves from Africa arriving on the island by 1520. Thereafter, the slave trade and Cuba’s plantation economy would boom as the island became Spain’s main base in the Caribbean for goods such as tobacco and sugar. Almost immediately, Cuba’s Indigenous population was decimated. At the time of Spanish arrival on the island, scholars estimate that roughly 112,000 Indigenous people inhabited the island, primarily belonging to the Taíno, Ciboney, and Guanajatabey tribes. Yet by the mid-sixteenth century, only several thousand Indigenous people had survived early colonial rule. By the late 18th century, slavery had completely transformed Cuba, driven by the immense transfer of human and financial capital. As the demand for coffee and sugar trades surged worldwide, American merchants collaborated with planters in Havana. The result? Cuba became the largest slave colony in all of Hispanic America. The system was exceptionally brutal, with violence functioning as a central role in sugar production. Torture, execution, and humiliation were the norm, dehumanizing an incredibly large chunk of the island’s inhabitants. At the mid-nineteenth century peak of Cuban slavery, enslaved persons accounted for roughly 45% of the island’s population.

 

America’s long history with Cuba dates to the 1800s. Between 1848 and 1854, the U.S. repeatedly attempted to annex or purchase the island from the Spanish government. Spain refused to sell Cuba, desperate to hold onto one of its last colonial territories in the Americas. However, civil strife had long been brewing in Cuba. Years of contention on the island led to the Ten Years' War fought between Spain and wealthy Cuban plantation owners and natives from 1868 to 1878. Continued slave uprisings, international pressure, and devastation from the Ten Years’ War would help lead to the abolishment of Slavery in Cuba in 1886. Still the fight for Cuban independence was far from over.

 

With the financial and logistical backing of the United States, Cuban rebels renewed their fight against Spanish occupation in 1895. The Spanish-American War began in April 1898 after the USS Maine, a battleship sent by President William McKinley on a peacekeeping mission to safeguard American citizens and U.S financial interests, sank in Havana harbor killing 260 crew members. The Spanish-American War would last for 114 days, resulting in a decisive victory for the United States. Upon the signing of the Treaty of Paris in 1898, Spain surrendered control of Cuba and ceded control of Puerto Rico, Guam, and the Philippines to the United States. The treaty would formally mark the end of the Spanish Empire, announcing the emergence of the United States as a global power. The U.S. military would occupy Cuba for four years before the country was formally granted independence in 1902.

 

Now independent, Cuba’s "Young Republic” emerged under the presidency of Tomás Estrada Palma. However, U.S. intervention in the island nation continued. The Platt Amendment, which stipulated terms for the withdrawal of remaining U.S. troops from Cuba following the Spanish-American war, was used to justify the Cuban Pacification—a period of American military intervention and occupation of the country from 1906 to 1909. Using the Platt Amendment as justification, the U.S. government would again intervene in Cuban affairs in 1912 to suppress an Afro-Cuban uprising and in 1917 to secure vital supplies of sugar during World War I. The centuries of colonial rule that Cuba suffered under the Spanish had solidified a blueprint that was maintained in the 19th and 20th centuries by foreign neo-colonialism led by the United States.

 

Spanish colonial rule and subsequent U.S interventionism left Cuba suffering from long-term systemic issues including inequality, corruption, institutionalized political meddling, and economic dependence on the sugar industry. The country’s political corruption and economic instability would sow the seeds for decades of authoritarian rule. Capitalizing on his success as a veteran general in the Cuban War of Independence fought against Spain from 1895 to 1898, Gerardo Machado was elected as the 5th President of Cuba in 1925. While his presidency was initially welcomed by the middle class, Machado would seize control of Cuban political parties and between 1927 and 1928 transition the country into a dictatorship under his rule. Facing severe economic crises during the Great Depression, loss of military support, and a massive general strike by university students and labor unions, Machado was forced to resign and flee into exile in 1933. After Machado’s ousting, Cuba experienced a brief "Age of Democracy” between 1940 and 1952, established under the 1940 Constitution which extended social security benefits for Cuban citizens and created a minimum wage for Cuban workers.

 

Cuba’s progressive movement wouldn’t last long. In 1952, a bloodless military coup led by General Fulgencio Bastista deposed the sitting President Carlos Prío Socarrás, canceled the Cuban constitution, and suspended Cuban elections. Basista had received American support as far back as September 1933 during the "Revolt of the Sergeants” as the U.S. government sought stability in Cuba following the collapse of Gerardo Machado’s dictatorship. Batista’s coup resulted in the Cuban Revolution, an armed uprising led by Fidel Castro's guerilla forces that began in 1953 and ended with the ultimate overthrow of the U.S.-backed Batista in 1959. With his brother Raúl Castro’s help, Fidel became Cuba’s new dictator, transforming the nation into a Soviet-aligned Communist state in the thick of the Cold War.

 

The Cuban Revolution, Fidel Castro’s alignment with the Soviet Union, and the nationalization of American assets in the country, led the United States to sever ties with Cuba on January 3, 1961. Just three months later, on April 17, 1961, President John F. Kennedy authorized the failed Bay of Pigs invasion. Alarmed at Cuba's alignment with the Soviets and seeking to covertly overthrow Cuba’s communist regime, the U.S. government launched the CIA-sponsored invasion calling for an amphibious assault team comprised of 1,400 CIA-trained exiles from Cuba coupled with two airstrikes on Cuban air force bases. B-26 Bombers were repainted to look like Cuban air force planes, but the ruse quickly fell apart in the media and the bombers failed to hit most of their primary targets, leaving Cuba’s air force intact. The ground invasion on the beaches of the Bay of Pigs similarly failed; insufficient ammunition, heavy fire, and bad weather led to the surrender of Brigade 2506, and prisoners remained captive in Cuba for 20 months.

 

Tensions between Cuba and the United States continued to escalate reaching a climax between October 16 and October 28, 1962 during the Cuban Missile Crisis; considered by many to be the closest the Cold War came to resulting in nuclear war. The crisis began when Soviet Premier Nikita Khrushchev reached a confidential agreement with Cuban Prime Minister Fidel Castro to place Soviet nuclear missiles in Cuba to deter any future invasion attempts by the United States. However, U.S. intelligence discovered the buildup of Soviet arms during routine surveillance flights over Cuba. The 13-day standoff ultimately ended with the U.S. agreeing to dismantle nuclear bases in Turkey and the Soviet Union agreeing to dismantle missile operations in Cuba.

 

Fidel Castro would continue to rule over Cuba until 2006, when he handed his duties as commander-in-chief to his brother Raúl due to an acute intestinal illness. Cuba’s national assembly officially elected Raúl Castro as President in 2008. Just eight years later, Fidel passed away at the age of 90, several years after retiring from public life. Raúl stepped down in 2018, remaining the First Secretary of the Communist Party until 2021. Succeeding him was Miguel Díaz-Canel, serving both as President of the Republic and First Secretary of the Communist Party of Cuba. Notably, Díaz-Canal is the first individual outside of the Castro family to lead the country since the Cuban revolution. However, his presidency has not been without contention; despite being elected to a second term in 2023, the largest anti-government protests since the Cuban Revolution broke out in 2021. Rather than address the erosion of personal freedoms and worsening living conditions for Cuban citizens, Díaz-Canal responded with the arrest and mass-trial of hundreds of dissenting Cubanos.

 

U.S. – Cuba Relations in the 21st Century

 

Relations between the U.S. and Cuba have historically been characterized by deep ideological differences and mutual mistrust. In 2014, under the administration of U.S. President Barack Obama, there was optimism for renewed ties between the U.S. and Cuba as President Obama and Prime Minister Raúl Castro announced that steps would be taken by the two countries to resume diplomatic relations. New embassies were opened in both Havana and Washington, D.C. in July 2015. Yet, the increase in diplomacy would not last. Renewed relations between Cuba and the United States collapsed in 2017 under the first administration of President Donald Trump. The collapse was caused by ideological differences between Trump and Obama, Cuba’s relationship with Venezuela, and the sudden unexplained neurological symptoms called "Havana Syndrome” that severely affected U.S. diplomatic personnel leading to a dramatic reduction of U.S. diplomats in Cuba and the expulsion of the Cuban embassy from Washington D.C.

 

Ideologically opposing the Obama administration’s "Cuban thaw" policy, the first Trump administration sought to put new economic and social restrictions on Cuba. The National Security Presidential Memorandum 5 of 2017 (reissued in 2025) directed the Secretary of State to identify and prohibit direct financial transactions with entities controlled by the Cuban military, intelligence, or security services.

 

Additionally, the Trump administration’s 2019 travel ban rescinded “person-to-person” travel licenses that allowed Americans to travel to Cuba. With Americans accounting for the second-highest number of travelers to Cuba, the new restrictions delivered a blistering blow to Cuba’s state-run tourism sector. Shortly before leaving office in 2021, the first Trump administration officially redesignated Cuba as a State Sponsor of Terrorism.

 

Under the administration of U.S. President Joe Biden, the Trump administration’s 2017 National Security Presidential Memorandum 5 was revoked. The Biden administration also proposed a rescission of Cuba’s designation on the list of State Sponsors of Terrorism. However, both of these actions were reversed once again under the second Trump administration. In January 2026, President Trump signed an executive order declaring Cuba as an “unusual and extraordinary threat” to U.S. national security and authorizing tariffs on goods from countries that sell or provide oil to the island. This recent pivot by the U.S. in its relations with Cuba has ramped up pressure on Cuba’s struggling economy, leading to greater doubts about Cuba’s ability to resolve domestic tension under the United States’ “iron fist” foreign policy approach.

 

Tensions with the Trump administration come at a time when Cuba faces an escalating humanitarian crisis. In the last ten years, Cuba has dealt with shortages of basic consumer products, climbing inflation, declining capital investment, reduced agricultural harvests, and a massive decrease in the country’s capacity to generate electricity. Between 2018 and 2022, Cuba’s electricity generation capacity dropped by 25%, resulting in frequent power outages on the island. Cuba is experiencing one of its worst crises since Fidel Castro came to power in 1959. Tourism has decreased by roughly 50% since 2017, and economists estimate that Cuba’s 2025 informal market inflation rate sits around 70%. With the average state salary hovering at just $15 to $16 USD per month, it is nearly impossible for the vast majority of Cuban citizens to lead healthy, happy lives. GDP growth in Cuba has contracted from 2023 through 2025. Sugar harvests are weak, falling below 200,000 metric tons in 2025, a 200-year low. As exports and tourist numbers have declined, food prices have surged; dwindling government rations have forced Cubans to turn to privately-run grocery stores, where the cost of eggs is roughly $8. The economic conditions in Cuba have been exacerbated by the expansive tariffs promulgated under the Trump Administration. Following U.S. Operation Absolute Resolve in January 2026, President Trump instituted the largest oil embargo on Cuba in decades. The Trump Administration’s Executive Order 14380 has effectively cut off Cuba from Venezuela's crude oil supply, its primary source of oil. This ‘maximum pressure’ campaign has sparked major fuel shortages in the country and has prolonged blackouts, leaving many Cubans without regular access to power. An already bad economic situation is being greatly exacerbated by the energy crisis, leaving no clear path forward for the Cuban people.

 

Where does Cuba go from here?

 

As U.S. sanctions and economic pressure on Cuba escalate, it is difficult to see a diplomatic, bilateral path forward between the two countries. The Department of Justice’s May 2026 indictment of former Cuban President Raúl Castro marks a new stage in U.S. – Cuba relations as the Trump administration continues to ramp up its interventionist approach. Earlier this year, in Operation Absolute Resolve, U.S. military forces captured President Nicolás Maduro and his wife, Cilia Flores. The two remain in federal custody in Manhattan, New York, facing charges of drug trafficking and narco-terrorism. Following the arrests, the Trump administration announced it would take control of Venezuela's oil sales, effectively curbing the sale of oil to Cuba which has been historically reliant on Venezuelan oil.

 

The U.S. war with Iran has increased geopolitical tensions and threatens to worsen Cuba’s oil and gas crisis. With ongoing American interventions in Venezuela and Iran, attempted regime change in Cuba may be a real possibility, something Cuba has seemingly already started preparing for. In May of 2026, findings published by Axios revealed that Cuba has acquired more than 300 drones from Russia and Iran, with classified intelligence suggesting that the drones could be used to target U.S. military vessels, Key West, Florida, and the U.S. Naval Base at Guantanamo Bay. The presence of Iranian military advisors in Havana is also worrisome as Cuba appears to be seeking knowledge on how Iran has resisted U.S. incursions. CIA Director John Ratcliffe travelled to Cuba, warning Cuban military officials to stave off attacks. Following the Axios report, Cuba’s embassy was quoted on X asserting that “Cuba has the right to defend itself against external aggression.”

 

While there are not yet visible signs of U.S. ground forces concentrating around the island, CNN reports that intelligence operations around Cuba have intensified. At the same time, Operation Epic Fury has failed to achieve immediate success in Iran and the United States has become bogged down in an unpopular war. As of early June 2026, a war that was supposed to last four to six weeks, is approaching week 15. And despite the assassination of Iran’s supreme leader Ayatollah Ali Khamenei none of the Trump administration's objectives—regime change in Iran, the total elimination of Iran’s nuclear program, the destruction of Iran’s ballistic missile arsenal, nor the destruction of Iran’s proxy network—have been achieved. As Americans struggle with the war’s fallout and rising gas prices, President Trump’s failure threatens his party’s results in the 2026 U.S. mid-term elections and undermined his administration's interventionist aims.

 

With Iran and Venezuela in the backdrop, Cuba remains in the crosshairs. Relations between Cuba and the United States are at a historically dangerous crossroads with the island facing heightened military tensions and possible domestic collapse. While the recent pattern of American interventionism suggests the island could be one of the next targets of U.S. military intervention, the failure of the Iran War and Operation Epic Fury could shift U.S. strategy. Though as of now, the American government seems unwilling to budge and instead has resorted to escalating legal and economic coercion. As Cuba and its economy continue to buckle under U.S. pressure and domestic societal tensions in Cuba continue to grow, a U.S. military operation in Cuba could very well be on the horizon.