Almost two decades ago, Miami’s Cuban exile community erupted in celebration outside the iconic Versailles restaurant when Fidel Castro announced he was temporarily stepping down due to illness.
Their joy was rekindled two years later when he resigned permanently, and again in 2016 upon his death, even as his brother Raúl Castro then held the presidency.
Today, however, Cuba faces an even more precarious situation: its economy is in free fall, the electric grid is collapsing, millions of citizens have fled, and the government is confronted by a formidable adversary in President Trump.
President Trump has significantly escalated pressure by blocking Cuba’s oil access, severely damaging its crucial tourism sector, and publicly stating that the Cuban government is “going down for the count.”
Both the Trump administration and numerous Cuban exiles, who have anticipated the collapse of Cuba’s Communist rule for almost seven decades, now believe this could truly be the decisive moment.
While past U.S. presidents employed various economic pressures, the Trump administration’s dramatic cutoff of fuel imports elevates the stakes considerably, given that oil is essential for nearly all functions of the country, from transportation to industry and agriculture.
Predictions of Cuba’s government collapsing are not new; they were famously made after the Soviet Union’s dissolution, when it ceased to be Cuba’s primary supporter, only to be proven incorrect.
However, this time, many experts suggest that the Cuban government’s continued existence is seriously jeopardized.
Officials from the Trump administration have reportedly assured members of South Florida’s Cuban exile community that the communist regime’s days are truly numbered.
Marcell Felipe, a leading Cuban exile figure in Miami and chairman of the American Museum of the Cuban Diaspora, who claims to have met with U.S. diplomats, stated, “The U.S. government has determined that Cuba must be free before the end of 2026. This is a plan in motion.”
Beyond oil, President Trump’s strategy has also focused on cutting off Cuba’s access to vital foreign currency, mainly from its tourism sector and its medical missions abroad, according to a senior State Department official who requested anonymity due to the sensitivity of diplomatic discussions.
Cuba’s tourism industry, already reeling from the Covid-19 pandemic, suffered further blows due to Trump administration policies that made it more difficult for Europeans to visit the U.S. if they had also traveled to Cuba.
Following the U.S. military’s capture of Venezuelan leader Nicolás Maduro, President Trump immediately ceased Venezuela’s oil shipments to Cuba. Historically, Venezuela had supplied Cuba with 35,000 barrels of oil daily in return for medical services provided by Cuban doctors.
Additionally, Mr. Trump imposed tariffs on any nation supplying oil to Cuba. Collectively, these actions have virtually eliminated Cuba’s only two oil providers—Venezuela and Mexico—at a time when the island is already experiencing widespread power outages. While Cuba produces some domestic oil, it only covers 40% of its daily needs, meaning a sustained lack of international shipments could lead to national paralysis, according to analysts.
President Trump claims the United States is engaged in discussions with high-ranking Cuban leaders, though he has offered no further details.
“Cuba is a failing nation,” Trump recently stated to reporters. “It has been for a long time, but now it doesn’t have Venezuela to prop it up. So we’re talking to the people from Cuba, the highest people in Cuba, to see what happens.”
The Cuban government declined requests for comment regarding this article.
However, Cuba’s deputy foreign minister, Carlos Fernández de Cossio, informed the EFE news agency that while “messages had been exchanged” with the Trump administration, no substantive dialogue was in progress.
He vehemently rejected any discussions concerning political or economic shifts, emphasizing that the United States has no more authority to dictate Cuba’s internal affairs than Cuba would have in prescribing how U.S. ICE agents should conduct migrant raids in Minneapolis.
“If people are thinking that there is division within the Cuban government, division within the political forces in Cuba, and a willingness,” he stated, “to capitulate to the unjustified and immoral pressure and aggression of the United States, that’s a mistaken interpretation.”
Juan Triana, a professor at the University of Havana’s Center for the Study of the Cuban Economy, highlighted that Cuba notably survived the severe ‘Special Period’ crisis in the 1990s, following the Soviet Union’s collapse.
“Everyone watched Cuba, expecting its collapse, and they lost that bet,” he commented. “U.S. presidents, one after another, have been wrong.”
Yet, a recent and rare news conference by Cuban President Miguel Díaz-Canel appeared to acknowledge the gravity of the nation’s challenges. He outlined plans to ration Cuba’s scarce domestic oil supply and to boost solar and wind energy initiatives, conspicuously omitting any mention of new oil imports.
The Cuban government has presented contradictory signals to the Trump administration, from sharply worded social media posts to a more moderate statement.
Cuba has even offered to renew cooperation with the United States on critical areas such as counterterrorism, anti-money laundering, drug trafficking prevention, cybersecurity, human trafficking, and financial crimes.
Concurrently, however, Cuba has also directed hostile actions towards Mike Hammer, the U.S. Embassy chief in Havana. He has been subjected to heckling and derogatory calls of ‘murderer’ by small groups of government supporters, and his diplomatic vehicle was surrounded five times during departures from meetings in various Cuban cities—incidents known as ‘acts of repudiation,’ according to the State Department.
An unauthorized U.S. official, speaking about the administration’s interactions with Havana, suggested that Cuban officials’ anxiety stems from a growing realization that their revolution is nearing its end.
The senior State Department official, elaborating on the White House’s strategy, clarified that most discussions with the Cuban government revolved around technical matters, such as repatriation flights, and lacked any substantive political discourse.
The core issue, the State Department official explained, isn’t a lack of communication, but a fundamental disagreement between both sides regarding the agenda for any potential talks.
The official indicated that if Cuban authorities were to propose substantial concessions, such as permitting greater private enterprise and allowing opposition political parties, the Trump administration would be prepared for more active engagement.
The Trump administration, the official noted, aims for discussions mirroring those in Venezuela, where the interim government has committed to measures promoting economic transformation and democracy.
However, such an approach is complicated by the absence of a Cuban figure equivalent to Venezuela’s interim leader, Delcy Rodríguez, who has shown willingness to appease the Trump administration, explained Ricardo Zúniga, a former Obama official involved in secret Cuba negotiations. Cuba’s government has a history of marginalizing officials perceived to have political ambitions.
A significant challenge noted by many experts, should Cuba’s government collapse, is the lack of a clear successor leadership, as the current regime has either imprisoned or exiled most opposition figures.
Peter Kornbluh, author of a history of clandestine U.S.-Cuba negotiations, suggested that discussions are likely already in progress.
“It makes sense that the U.S. and Cuba are engaged in back channel talks, even if they are the result of criminal coercion from the Trump White House,” commented Mr. Kornbluh, a vocal critic of U.S. hard-line economic policies. “Dialogue, even under duress, is preferable to overt U.S. aggression and offers a potential off-ramp for both sides.”
The 2013 negotiations during the Obama administration were so clandestine that even the State Department was unaware. These discussions, facilitated by the Vatican and held in both the Vatican and Canada, ultimately resulted in renewed diplomatic relations and a short period of relaxed travel restrictions.
Those talks operated on the premise that fostering private business and improving living conditions in Cuba would eventually lead to regime change. However, the Cuban government ultimately suppressed these economic openings. Conversely, Mr. Trump’s current strategy, as Mr. Zúniga explained, is predicated on the belief that economic and social collapse will force the government to yield.
“I think they are trying to create a condition of extraordinary stress, akin to a war, in Cuba, hoping to extract concessions from the Cuban government,” he stated. “But the Cubans simply have no vision for any plan that would see them relinquish power.”
Ada Ferrer, a Princeton University history professor and author of the Pulitzer Prize-winning ‘Cuba, an American History,’ acknowledged that previous predictions of Cuba’s government downfall proved incorrect. However, she noted a crucial difference this time: there is no longer a powerful benefactor, like post-Soviet Venezuela, ready to rescue Cuba’s spiraling economy.
“This time,” she concluded, “feels profoundly different.”
Jack Nicas also contributed reporting for this article from Mexico City.