The Trump administration appears to be setting its sights firmly on Havana, with Secretary of State Marco Rubio taking the lead in this initiative.

Following the January capture of Venezuelan leader Nicolas Maduro and a significant military campaign involving Iran, Rubio, a prominent figure in Trump’s Cabinet, is now shifting focus to Cuba, a nation that has resisted U.S. influence for over seventy years.

According to two insiders, Rubio’s ambition is to orchestrate a comprehensive ‘global cleanup’ of socialist governments throughout the Western Hemisphere.

In contrast to the situation in Venezuela, Rubio is confident that Cuba’s communist regime can be pressured into compliance without deploying American troops to the island.

“The year 2026 will be a pivotal moment,” a diplomatic source with knowledge of the strategy shared with the Daily Mail.

The primary tool in this effort: oil.

With the Maduro regime dismantled and Washington now effectively controlling Venezuela’s oil exports, the fuel shipments that kept the lights on in Havana have been cut off. 

Two State Department insiders tell the Daily Mail that Rubio is playing a careful long game: He avoids raising Cuba directly with Trump or the cabinet unless other officials bring it up first – letting the oil squeeze do the talking.

‘He’s playing it very, very carefully. He pretty much only talks about Cuba when he’s asked about it… but ultimately, the president is putting a lot of trust in Rubio,’ one former State official explained.

It is a calculated, peace-through-strength chokehold, and Trump says it is already working. 

The President revealed on Saturday that the communist regime is ‘in its last moments of life’ and that he would ‘take care of Cuba.’ 

The Trump administration has a target on Havana, and Secretary of State Marco Rubio is hovering over the scope

A woman sits in her home during a blackout in Havana on March 5, 2026. Cuban authorities said on March 5 that electricity is slowly coming back to end a blackout that stemmed from a lack of fuel under US pressure

With the Maduro regime dismantled and Washington now effectively controlling Venezuela’s oil exports, the fuel shipments that kept the lights on in Havana have been cut off

A man in Cuba carries raw materials along a street in Havana after a power outage

Rubio, the son of Cuban exiles who has made the fall of Castroism his life’s mission, is now the dual–hatted architect of this strategy, serving as both Secretary of State and acting National Security Advisor.

He been given total space on the Western Hemisphere by Trump to be the lead architect of this policy, the Daily Mail has learned.

A source close to Secretary Rubio tells the Daily Mail that the administration is so confident in their new strategy that they believe the Cuban regime will be ‘gone by the end of the year.’ 

Insiders familiar with their plans describe it as a financial crippling to the current regime that involves cutting Cuba off from economic assistance from the rest of the world, and to prepare a recovery plan.

Once the oil dries up, they hope the ‘oil squeeze’ will lead to structural collapse. 

The target: Miguel Diaz–Canel, the President of Cuba and First Secretary of the Communist Party of Cuba, and General Alvaro Lopez Miera, the Minister of the Revolutionary Armed Forces. The Cuban military controls the majority of the Cuban economy, including oil distribution and tourism.

‘I will just say that Cuba is right where we want them,’ a White House source familiar with the internal conversations explains. 

Blackouts have plunged Cuba into darkness. Garbage is piling up on the streets of Havana. And the communist leadership, sources say, is feeling the pressure.

Venezuela was pumping a critical 55,000 barrels of crude into Cuban ports every day before the January raid, a flow that has reportedly now plummeted to near zero, according to an analysis by the Center for Strategic and International Studies and Reuters shipment tracking data.

Even secondary suppliers like Mexico have halted shipments under the threat of US tariffs.

‘Cuba is a beggar country abandoned by its friends and desperate to survive an oil embargo that could soon shut down its national economy and lead to structural collapse,’ said John Sitilides, a former State Department consultant.

The Daily Mail has reported on a long–standing ‘tug of war’ over Latin American policy that has ended between Rubio and Ric Grenell, Maduro’s former negotiator.

The two have frequently clashed over their competing visions for the region.

It is a calculated, peace through strength chokehold, and the administration says it is already working

Insiders familiar with their plans describe it as a financial crippling to the current regime that involves cutting of Cuba from economic assistance from the rest of the world, and a recovery plan

‘There is no Ric Grenell wrestling for the steering wheel in Cuba anymore,’ the State Department insider revealed. ‘Rubio feels a sense of relief; it’s an open field for him now.’

Grenell played an early role in South America as Trump’s envoy for special missions. Rubio ultimately emerged as the winner in leading policy decisions as the former special envoy was sidelined. 

Trump is reportedly hell–bent on forcing a major political shift in the country. 

Latin America experts detail a scenario that could play out given this strategy. One where the police lose the streets to a hungry, desperate population, and the ultimate survival of the regime falls to the military high command. 

One White House insider suggests a ‘palace coup’ is the likely endgame, where top generals, desperate to protect their own vast business empires, choose to topple President Miguel Díaz–Canel rather than fire on their own people, potentially installing a reformist junta to negotiate a lifeline with the US administration.

‘They [the Cuban regime] are already being strangled. The government of Cuba has been living off of other people’s money for decades. United Nations, European countries, countries like Japan or Switzerland or others who lent money thinking they would be paid and they never did,’ former US envoy Otto Juan Reich explained to the Daily Mail. ‘Pretty much everyone has learned that lesson.’ 

Reich was the Assistant Secretary of State under President George W. Bush and later the Special Envoy for Western Hemisphere Initiatives. He also worked for President Ronald Reagan and was a former US ambassador to Venezuela. 

He argues that without Venezuelan oil and with a tightening US naval blockade, the regime simply cannot survive.

A man carries a television next to a photo of late Cuban leader Fidel Castro in Havana. Cuba’s communist government lost one of its key diplomatic supporters, and a vital source of fuel for the country in January when US forces toppled Venezuelan President Nicolas Maduro, effectively taking control of Venezuelan oil exports. The country had previously relied on Venezuela for about half of its fuel needs

In another stunning development, Rubio is reportedly bypassing the official government of President Miguel Díaz–Canel entirely, Axios originally reported. Instead, he has opened a high–stakes backchannel with the one man the administration believes holds the real power: Raul Guillermo Rodriguez Castro, the grandson and former head of security for Raul Castro

Yet history warns against underestimating the regime’s proven resilience. Having survived the brutal 1990s ‘Special Period’ economic crisis when trade plummeted by 80%, Havana is no stranger to governing by candlelight. 

Regardless, the administration says they feel confident Cuba’s government will be toppled this time around. 

In another stunning development, Rubio is reportedly bypassing the official government of President Miguel Díaz–Canel entirely, Axios originally reported.

Instead, he has opened a high–stakes backchannel with the one man the administration believes holds the real power: Raul Guillermo Rodriguez Castro, the grandson and former head of security for Raul Castro. 

‘They are expecting a managed transition that ensures stability on the ground while making irreversible and inexorable progress towards a different situation,’ the former Senior State Department official said. 

‘But the Trump administration won’t be satisfied with just a regime in Havana that is under control by some member of the Castro family.’

Rep. Carlos Gimenez, second from left, at the Republican Members Issue Conference with President Donald Trump. A source familiar with the conversations between the President and his advisors says Trump and Rubio are also getting advice from Cuban–Americans in Congress like Gimenez

However, pushing too hard for total systemic collapse carries severe domestic risks for the administration. 

As Sitilides points out: ‘In 1980, 125,000 refugees fled Cuba for Florida. Civil chaos in Cuba today could lead to more than a million refugees, ten times the impact on Florida and the southern United States, and a potential political calamity for the Republican Party in the November mid–term elections.’

To avoid this worst–case scenario, the administration is favoring strategic leverage over total disruption.

‘A sudden ‘de–Baathification’ overthrow that led to twenty years of carnage in Iraq is not the White House model for Cuba,’ Sitilides explained. ‘Rather, a short–term ‘regime management’ policy in Washington towards Havana can lay the long–term pathway to a hopeful democratic transition, as the experiment is similarly proceeding in Venezuela.’

A source familiar with the conversations between the President and his advisors says Trump and Rubio are also getting advice from Cuban–Americans in Congress, Cuban businessmen he has worked with Mar–a–Lago with and even individuals ‘recently named ambassador who have the personal experience.’ 

Those he has been speaking with more closely include Republican Representatives Mario Diaz–Balart, Maria Elvira Salazar and Carlos Gimenez from Florida; the self–dubbed ‘Three Crazy Cubans.’

Trump is reportedly hell–bent on forcing a major political shift in the country, telling a group of Latin American leaders Saturday at the Shield of America’s event that the communist regime is ‘in its last moments of life’ and that he would ‘take care of Cuba’

The list of ambassadors Trump and Rubio reportedly has been seeking advice from include Ambassador to Panama Kevin Marino Cabrera, Ambassador to Argentina Peter Lamelas, Ambassador to Peru Bernie Navarro and the Ambassador to Spain Benjamin Leon Jr. 

The Daily Mail reached out to the ambassadors for comment. They did not immediately respond. 

While the White House remains publicly tight–lipped about regime change, insiders say the message to Havana is clear: negotiate a transition now, or collapse under the weight of the blockade.

As the former Senior State Department official put it: ‘They believe that [preventing oil from coming in] will give them the leverage to make the changes that will lead to a new political situation on the island.’

If Rubio’s plans hold, the communist experiment in Cuba may not survive the year.

‘Their goal is to make Cuba’s leadership as desperate as possible,’ the White House sources familiar with plans tell the Daily Mail.  

Yet, regional experts warn that cornering Havana comes with a final, dangerous wildcard.

‘The looming backfire risk is ignited guerilla warfare elsewhere in Latin America, especially in Colombia and Venezuela where Havana has trained thousands of fighters,’ Sitilides warned.

‘Cuba is a house of cards,’ Reich explained. ‘It has never worked, but it has enormous potential. The sooner that these people can be removed peacefully and replaced, not by other crooks, the better. But there are plenty of people inside and outside the island who can then rebuild. Cuba can become one of the rising stars of Latin America again.’

Once the oil dries up, they hope the ‘oil squeeze’ will lead to structural collapse. The target: Miguel Diaz–Canel, the President of Cuba and First Secretary of the Communist Party of Cuba, and General Alvaro Lopez Miera, the Minister of the Revolutionary Armed Forces. The Cuban military controls the majority of the Cuban economy, including oil distribution and tourism

A White House aide familiar with ongoing plans says that a plans for Cuba’s recovery are already being plotted.  

‘They are already working on Cuba’s economic recovery plans at [the State Department]. That shows you how confident they feel that this will be achieved,’ the aide explains

A White House official confirms to the Daily Mail that there are active conversations with Cuba.

‘We are talking to Cuba, whose leaders should make a deal. Cuba is a failing nation whose rulers have had a major setback with the loss of support from Venezuela and with Mexico ceasing to send them oil,’ A White House spokesperson told the Daily Mail.