Emboldened by the removal of its president, , from the United States, the administration is seeking figures from within the Cuban government who could contribute to a deal aimed at ousting the Communist regime by the end of the year, according to sources familiar with the matter.
The Trump administration believes Cuba’s economy is on the brink of collapse and that the government has never been more fragile, especially after losing a key supporter, Maduro, the same sources said.
While there is still no concrete plan to end the communist rule that has held power on the Caribbean island for nearly seven decades, senior US officials view Maduro’s arrest and subsequent concessions from his remaining allies as a model and warning for Cuba.
“I strongly advise them to make a deal. BEFORE IT’S TOO LATE,” President Trump wrote in a Jan. 11 social media post, adding that there will be “NO MORE OIL OR MONEY” for Cuba.
In meetings with Cuban exiles and civic groups in Miami and Washington, administration officials are focusing on finding someone within the current regime who “will understand where things are going” and want to make a deal, a US official said.
The military dimension
was facilitated, according to government officials, by a person in the Venezuelan leader’s inner circle. The US military operation in Caracas resulted in the death of 32 Cuban soldiers and intelligence officers who were part of Maduro’s security guard.
Although the US has not publicly threatened to use military force against Cuba, Trump administration officials say privately that the bold operation that ousted Maduro should serve as an indirect threat to Havana.
U.S. intelligence estimates paint a bleak picture of the island’s economy, which is plagued by chronic shortages of basic goods and medicine, as well as frequent power outages, according to sources familiar with the analyses.
The fate of Cuba has been inextricably linked to that of Venezuela for years. Subsidized Venezuelan oil has been a mainstay of the Cuban economy since Hugo Chavez took power in 1999. Washington plans to weaken the regime by cutting off that oil supply, which has kept the “lights on” in Cuba, according to senior US officials. Economists warn that Cuba could run out of oil within weeks, bringing the economy to a complete standstill.
The Trump administration is also targeting Cuban medical missions abroad, the most important source of hard currency for Havana, including through visa bans on Cuban and foreign officials accused of facilitating the program.
The bet of the American strategy
Trump and his inner circle, many of whom have ties to Florida, see the overthrow of the communist regime in Cuba as the defining test of the president’s national security strategy to reshape the Western Hemisphere, officials said. Trump is calling the US deal with Venezuela a success, citing the cooperation of interim President Delsy Rodriguez as proof that Washington can enforce its terms.
“Cuba’s leaders are incompetent Marxists who have destroyed their country and suffered a serious blow with the Maduro regime, which they themselves supported,” a White House official said, reiterating that Cuba must “make a deal before it’s too late.”
In a statement, the State Department said it is in the national security interest of the US that Cuba “be effectively governed by a democratic government and refuse to host military and intelligence services of our adversaries.”
Some Trump administration officials note that the president is rejecting regime change strategies of the past. Instead, he pursues deals where possible and seizes opportunities when they arise. As in Venezuela, that could mean an escalation of pressure, while signaling that the White House remains open to a negotiated “exit,” a senior official said.
Many Trump allies expect nothing less than the end of communist rule in Cuba. However, removing an already cash-strapped government could trigger serious unrest and a humanitarian crisis similar to the one Trump sought to avoid in Venezuela, where he chose to keep top loyalists in place.
The Havana regime has withstood decades of intense American pressure, from the 1961 CIA-backed Bay of Pigs invasion to the harsh 1962 embargo, which has tightened over time. The two countries became rivals shortly after the Castro brothers descended from the Sierra Maestra mountains with their guerrilla group in 1959.
All this leaves the US looking for a clear plan for the day ahead and who could replace the current regime, according to the same sources. The Venezuelan model may be more difficult to apply in Cuba, which is a one-party, Stalinist-style state that bans political opposition and where civil society is virtually non-existent. In contrast, Venezuela has an organized opposition, a history of mass protests, and electoral processes.
“They’re a much tougher nut to crack,” said Ricardo Zuniga, a former Obama administration official who was involved in the negotiations for the brief US-Cuba rapprochement from 2014-2017. “There is no one who is tempted to cooperate with the American side.”
Reactions and challenges
In its nearly 70 years, the Cuban government has never been willing to negotiate changes to its political system, limiting itself to piecemeal and minor economic reforms.
Trump believes the end of the Castro era will cement his political legacy and achieve what John F. Kennedy failed to do in the 1960s, said a US official who handled the issue during Trump’s first term. This is also a constant goal of Secretary of State Marco Rubio, the son of Cuban immigrants who settled in Florida in 1956.
In Miami, where the view for years has prevailed that the path to regime change in Havana is through a change of government in Caracas, Maduro’s ouster has sparked celebrations and heightened expectations that Cuba will be next. Prominent Trump allies and US lawmakers have posted AI-generated videos depicting a post-communist utopia: ships arriving from Miami, family reunions and Trump and Rubio driving a 1950s convertible past the glitzy hotels of a “liberated” Cuba.
“The regime has to choose whether to leave or take better care of its people,” Deputy Under Secretary of State for International Assistance Jeremy Lewin said last week, referring to $3 million in humanitarian aid for hurricane victims sent to Cuba through the Catholic Church in American-flagged boxes.
Havana has publicly rejected this logic. The Cuban government is still largely controlled by 94-year-old Raul Castro, Fidel’s younger brother, while 65-year-old President Miguel Diaz-Canel, an unpopular party official, handles day-to-day governance.
“There is no case of surrender or capitulation, nor any understanding based on coercion or threat,” Díaz-Canel, wearing a green military uniform, said at a recent memorial service for members of the Cuban security forces who were killed in Caracas protecting Maduro.
The Cuban government has proven particularly effective at suppressing dissent among an impoverished population. It has faced just two mass uprisings: in 1994 in Havana and in 2021, when tens of thousands of Cubans took to the streets across the island. Human rights organizations estimate that more than 1,000 political prisoners are in prison.
As tensions with the US escalate, Cuba held a national defense day on Sunday. Citizens were trained in a “whole people’s war” scenario to repel invaders.
Television footage showed elderly men firing battered Kalashnikovs and middle-aged women planting mines. “It’s theater,” commented Joe Garcia, a Cuban-American and former Democratic congressman from Florida with contacts in the Cuban leadership. “This is a country that can’t pick up its trash and is pretending to be preparing for a clash with the superpower next door.”
On some evenings, with no electricity and little gas to get around, Havana’s streets are plunged into darkness and silence, broken only by the metallic sound of wooden spoons banging pots — an anonymous form of protest heard from open windows, balconies and rooftops late at night, when the power has been out all day and desperation peaks.
