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Note: This article is the second part of a two-part article series discussing the history and context of Donald Trump’s recent threats against Cuba.
In a White House press conference on June 4th, 2026, United States (U.S.) President Donald Trump stated, “[he’ll] take care of Cuba.” This comes on the heels of multiple aggressive statements towards the island nation. Trump has brought Cuba to the brink of collapse. Trump is not the first American President to threaten Cuba. It has been an American tradition for over sixty years, aside from a short reprieve under President Obama.
The island has not received an oil shipment in months. Hunger and malnutrition are expanding, increasing the risk of death. There are days when the whole country is in blackout conditions. Cuba’s economy no longer functions, and the Cuban government is scrambling to find relief.
Despite Cuba’s attempts to reform, Trump and the U.S. have maintained their threatening posture towards the island. It seems in the U.S.’s eyes, Cuba can do no right. America will not change its approach to Cuba, even when the population is suffering. The last time Cuba went through similar desperation, the U.S. offered little support.
No Reprieve
As Cuba recovered from the special period’s ruin, the U.S. continued repressing the island. President Bill Clinton authorized a law in reaction to the 1996 shootdown of Cuban exile planes. The law allowed Americans to sue companies using their former property that the Cuban government had seized.
Additionally, Clinton asked the U.S. military to plan a massive missile and air strike against Cuban military bases; the U.S. military advised against it. The new law called for sanctions against countries holding close ties with Cuba, an unusual move. The law codified the embargo within U.S. law, meaning future Presidents seeking to improve relations now depended on congressional authorization.
The Libertad Act caused U.S.-Cuban relations to remain in a frozen Cold War state. When allowed to improve relations with Cuba, the U.S. would persistently maintain its aim to topple the revolution.
Despite Pope John Paul II’s visit to Cuba in 1998, where he called for finally ending the embargo, Clinton only made some minor changes. In March, two months after the Pope’s visit ramped up international pressure, Clinton reauthorized remittances, humanitarian charter flights, and the sale of medication and medical equipment to Cuba. These were meagre steps in the right direction.
Bush Backtracks
After George W. Bush narrowly won the 2000 Presidential election – in part thanks to Cuban-Americans in Florida – he overturned Clinton’s modest policy changes. Bush was committed to overthrowing Castro, just like previous presidents.
His first Cuba policy was the Initiative for a New Cuba. It called for the Cuban government to enact democratic and free-market reforms in exchange for the U.S. easing the embargo. Bush claimed these reforms would allow ordinary Cubans to benefit from trade, and without them, only the “Castro regime” would benefit. Contradicting this statement, the special period’s devastation hurt the people, while the government remains in power.
(Photo by White House Photographer Tina Hager via Wikimedia Commons/Public Domain)
Bush was convinced that Cuba’s government was crumbling and needed one final push. He created the Commission for Assistance to a Free Cuba, a task force charged with generating a report on how to bring “an expeditious end of the dictatorship.”
In 2004, the commission published its report, and Bush swiftly implemented its recommendations. He restricted remittances, reduced the number of authorized visitors, and increased policing of Cuban waters. Bush also spent hundreds of millions of dollars on “efforts to promote freedom and democracy in Cuba.”
These efforts included airing anti-communist and anti-Castro broadcasts across the island, as well as paying government dissidents. Rather than lifting the embargo – which is free and mutually beneficial – Bush’s expensive efforts proved wasteful.
The Obama Thaw
Obama opted for a different approach, realizing that American policy towards Cuba was acutely unsuccessful. Shortly after his inauguration in 2009, he lifted restrictions on remittances and family travel. He then began quietly negotiating with Cuba through the Vatican.
The late Pope Francis had sent letters to both Obama and Raúl Castro, imploring them “to resolve humanitarian questions of common interest, including the situation of certain prisoners, in order to initiate a new phase in relations.” Following the Pope’s efforts, the Obama Administration announced it was normalizing relations with Cuba on December 14th, 2024. A month later, the Treasury Department declared it was reducing financial restrictions on Cuba.
In May 2015, Obama removed Cuba from the list of state sponsors of terror, allowing the island to reenter the global economy. This action also showed goodwill towards the Cuban government and that the U.S. was serious about restoring relations.
The U.S. and Cuba reopened their embassies in their respective countries two months later. Officials from both countries engaged in state visits and planned bilateral agreements on economic policy and law enforcement. There appeared to be hope that America’s six-decade war on Cuba could come to an end.
In March 2016, Obama became the first sitting U.S. President in 88 years to visit Cuba. It was a joyous celebration. Obama watched the Tampa Bay Rays play an exhibition game against the Cuban national team. He entered the stadium to thunderous applause as a Cuban choir sang the American national anthem. Accompanying Obama were Raúl Castro, Derek Jeter and Jackie Robinson’s widow, Rachel Robinson.
(Photo by White House Photographer Chuck Kennedy via Wikimedia Commons/Public Domain)
Obama lifted nearly every sanction and restriction presidential power allowed for. The U.S. was open to Cuban medical trials, and the Treasury and Commerce Departments expanded development grants towards Cuba. Most importantly, Americans could now import Cuban tobacco and alcohol to their hearts’ content, as long as it was for personal consumption.
Obama did not remove all the sanctions, as Congress held the keys to ending the embargo, but his policies had a profound effect. American banks – the backbone of the global financial system – could now do business in Cuba. This allowed for tremendous cash flow. Workers benefited, and private enterprise grew.
Trump Turns Back the Clock
Upon his inauguration, Trump rapidly undid Obama’s progress. He restored Bush’s limits on remittances and family visits, as well as reimposed restrictions on American businesses operating in Cuba. He then downsized the American embassy in Havana to the minimum staff necessary, rendering it meaningless.
Trump then reinstated bans on Americans from traveling to Cuba for educational and cultural exchanges. In 2020, he forbade Americans from staying at state-owned hotels in Cuba, making the act a criminal offense. He additionally banned companies from doing business with corporations tied to the Cuban government.
Trump’s efforts to strangle Cuba could not have come at a worse time. The restrictions had a devastating impact during the COVID-19 pandemic. Foreign companies could not sell medical equipment, such as ventilators, to Cuba, for fear of U.S. reprisals. These restrictions killed people. Yet, Cuba adapted again, creating its own effective vaccine.
In one of his final acts before ending his first term, Trump returned Cuba to the list of state sponsors of terror. This increased hardship in Cuba at a critical time. Five years after Obama offered a glimmer of hope, Trump reinstated Cuba’s darkest hours.
Biden Cowers
Despite former U.S. President Biden campaigning on restoring Obama’s Cuba policy, he maintained Trump’s. Biden extended humanitarian sanction waivers to Iran, Syria, and Venezuela, but not to Cuba. Biden did nothing to ease the island’s struggles, allowing the 60-year-old restrictive policy to remain.
Biden only changed course after Trump won his second term. In the dying days of his presidency, Biden removed Cuba from the list of state sponsors of terror. This was an incredibly cowardly move. Biden could have done this on his first day, yet he chose to prolong Cuba’s suffering.
While he was aware Trump would have an aggressive approach towards Cuba, Biden acted when it was too late. Trump had just nominated Marco Rubio – a notorious Cuba Hawk – to be secretary of state.
Maximum Pressure
On his first day back in office, Trump reinstated Cuba to the list of state sponsors of terror, but that was not all he did. Trump entered his second term intent on eliminating what remained of Cuba’s revolution.
He imposed stricter restrictions on remittances and travel, and doubled down on the embargo, seeking to destroy the Cuban economy. Capturing Maduro was also part of his Cuba policy. Ever since Hugo Chavez took power in Venezuela, the U.S. provided Cuba with affordable energy. Shortly after capturing Maduro, Trump stated Cuba was “in a lot of trouble,” and urged it “to make a deal BEFORE IT IS TOO LATE.”
(Photo by Donald J. Trump via Wikimedia Commons/Public Domain)
Trump was overtly threatening the island. These threats were to be taken seriously, as the last time Trump was negotiating with adversaries, he attacked them. During the Iran nuclear negotiations in the summer of 2025, he bombed their nuclear facilities. Before kidnapping Maduro, he had been in months-long negotiations with Venezuela.
Since the U.S. intervention, Venezuelan oil no longer flows. Trump also sought to block any oil from reaching Cuba. The island received its last oil shipment in March. Cuba is collapsing. Trump is now threatening military action, signalling what the U.S. ambition was all along. The island is in a state of disrepair, likely leading Trump to think it’s ripe for the taking.
The End?
After months of stating “Cuba is next” and indicting and sanctioning Cuban officials, the U.S. is openly flying military aircraft around the island. These were the same signals Trump sent before kidnapping Maduro and launching the disastrous U.S.-Israeli war against Iran.
Trump recently said in an interview that, “[a] Cuba operation could mirror Venezuela.” It is not a matter of if, but when. American action against Cuba is foreseeable, only depending on the end of the U.S.-Israeli war against Iran
Last time the U.S. threatened Cuba this way, they had a powerful ally to back them up, but this time Cuba does not have Khrushchev to come to their aid. This is not just Trump’s doing. This is the culmination of six decades of U.S. policy.
Edited by Alexas Vieira
