7 Explosive Signs Trump Is Targeting Cuba After Venezuela as the US seeks a deal to oust the communist regime. Weeks after a dramatic US operation that resulted in the capture of Venezuelan President Nicolás Maduro, the Trump administration is now turning its focus to Cuba, according to a detailed report by The Wall Street Journal.
Senior US officials cited by the newspaper say Washington believes the Communist government in Havana is more vulnerable than at any time in decades, weakened by economic collapse, fuel shortages, and the sudden loss of its most important ally and benefactor — Venezuela.
The strategy, officials say, is not yet a full-blown invasion plan. Instead, it centres on identifying insiders within the Cuban state who may be willing to negotiate a political “off-ramp” in exchange for an orderly transfer of power — a playbook the administration believes worked in Venezuela.
But Cuba is not Venezuela. And history suggests that attempts to force political change in Havana carry risks that extend far beyond the island itself.
7 Explosive Signs Trump Is Targeting Cuba After Venezuela
From Caracas to Havana: Why Cuba Is Now in Washington’s Crosshairs
According to US officials speaking to The Wall Street Journal, the thinking inside the Trump administration has shifted decisively since January 3, when US forces captured Maduro in a high-risk operation in Caracas that also killed dozens of Cuban security and intelligence personnel stationed there.
That operation, officials say, reshaped Washington’s assessment of what is possible.
A Post-Venezuela Confidence Boost
US officials argue that two developments have emboldened them:
- The successful extraction of Maduro, reportedly aided by an asset inside his inner circle
- The collapse of Cuba’s oil lifeline, after Venezuelan supplies were cut off following Maduro’s removal
In Washington’s view, Cuba’s long-standing ability to withstand sanctions and isolation was anchored to cheap Venezuelan oil, exchanged for Cuban medical, security, and intelligence support.
With that arrangement now broken, US intelligence believes Havana is facing a crisis it may not be able to manage indefinitely.
Trump’s Public Warning: ‘Make a Deal Before It Is Too Late’
President Donald Trump has made little effort to conceal his intentions.
In a January 11 Truth Social post, Trump issued a stark warning to Cuba’s leadership:
“THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA — ZERO!
I strongly suggest they make a deal, BEFORE IT IS TOO LATE.”
US officials say this message was not rhetorical. It was meant to signal that economic pressure will intensify, while also leaving open the possibility of negotiation.
Behind closed doors, administration officials describe this as a dual-track strategy:
- Maximum pressure to weaken the regime
- A potential negotiated exit for senior leaders, including Raúl Castro and President Miguel Díaz-Canel
The Core US Strategy: Find Insiders Willing to Cut a Deal
Unlike Cold War-era efforts to overthrow Fidel Castro, the current US approach is reportedly focused on elite defection rather than mass uprising.
Meetings With Exiles and Civic Groups
According to The Wall Street Journal, US officials have held a series of meetings in:
- Miami
- Washington, DC
These sessions involved Cuban exile groups, analysts, and civic leaders, with a singular goal:
identify individuals inside Havana’s power structure who may be open to negotiation.
One official described the approach bluntly:
“We’re looking for people who see the writing on the wall.”
The model, US officials say, is Venezuela — where an insider allegedly helped US forces locate and isolate Maduro.
Why Washington Thinks Cuba Is Vulnerable Now
US intelligence assessments cited in the report paint a bleak picture of Cuba’s economy.
An Economy on the Brink
According to officials familiar with the assessments:
- Chronic shortages of food and medicine
- Rolling blackouts across much of the country
- Severe fuel shortages, with analysts warning Cuba could run out of oil within weeks
Nearly 90% of Cubans live below the poverty line, according to intelligence estimates cited by US officials.
The loss of Venezuelan oil has proven especially devastating. For more than two decades, subsidised crude from Caracas kept Cuba’s electricity grid running. Without it, the system is failing.
Oil as a Weapon: Cutting the Regime’s Lifeline
Ending the Cuba-Venezuela Energy Axis
Cuba has depended on Venezuelan oil since the late 1990s, when Hugo Chávez rose to power.
In return, Havana provided:
- Doctors and nurses
- Intelligence officers
- Security personnel
With Maduro gone, the Trump administration has moved to block any remaining oil flows between the two countries.
US forces have already:
- Seized Cuba-bound tankers
- Pressured third-party intermediaries
- Sanctioned Cuba’s state oil importer, Cubametales
Trump’s message has been unequivocal:
no oil, no money, no status quo.
Cuba’s Scramble for Fuel: Africa, Mexico, and Desperation
Facing a collapse in energy supply, Cuba has begun searching for oil far beyond its traditional partners.
African Shipments
Independent media reports indicate that a tanker carrying fuel departed Togo bound for Havana, likely representing a cash purchase via European intermediaries.
Energy experts caution that:
- The shipment is not large enough to stabilise the grid
- Such purchases are financially unsustainable under sanctions
Mexico’s Limited Support
Mexico has sent oil shipments worth hundreds of millions of dollars, but analysts say these volumes cannot replace Venezuelan supply.
Even with these stopgap measures, Cuba continues to experience nationwide blackouts, with officials warning that outages could affect up to 60% of the country at peak times.
Targeting Medical Missions: Cutting Cuba’s Cash Engine
Beyond oil, the Trump administration is also hitting Cuba’s most important source of hard currency:
overseas medical missions.
Why Medical Missions Matter
Cuba deploys tens of thousands of doctors abroad, earning billions of dollars annually — a lifeline for the state.
US officials accuse Havana of:
- Exploiting medical workers
- Seizing the majority of their wages
Washington has imposed:
- Visa bans on Cuban officials
- Sanctions on foreign facilitators
The goal, officials say, is to starve the regime of cash, not humanitarian aid.
The Venezuela Blueprint — and Its Limits
Inside the administration, the January 3 Venezuela operation is being treated as proof of concept.
Why Officials Believe It Worked
- Insider cooperation
- Rapid, decisive action
- Immediate pressure for political concessions
But experts warn that Cuba is fundamentally different.
Why Cuba Is a ‘Much Tougher Nut to Crack’
Former US officials with Cuba experience caution that the Venezuela model may not translate.
Ricardo Zúñiga, who helped negotiate the Obama-era détente, told WSJ:
“There’s nobody who would be tempted to work on the US side.”
Key Differences
- Cuba is a single-party Stalinist state
- No legal opposition parties
- Minimal civil society
- Near-total state surveillance
Unlike Venezuela, Cuba has not held competitive elections or tolerated organised opposition.
Cuba’s Leadership: Old Guard Still in Control
Despite stepping down formally, Raúl Castro, 94, remains the ultimate power broker.
President Miguel Díaz-Canel, widely seen as unpopular, manages day-to-day governance but lacks independent authority.
Cuban officials insist:
“There is no surrender or capitulation possible.”
The regime has responded to US pressure with:
- Mass demonstrations
- Military drills
- National defence exercises
International Response: Russia, Iran, and Global Tensions
Russia
Moscow has condemned US pressure as “blackmail” and reaffirmed support for Havana.
Iran
Cuba’s ties with Iran have deepened, further alarming Washington.
Global Concerns
Many countries fear:
- A humanitarian crisis
- Mass migration
- Regional instability
Humanitarian Risks: The Greatest Unknown
Even US officials privately acknowledge the danger.
A sudden collapse of the Cuban state could trigger:
- Food shortages
- Medical system failure
- A refugee crisis affecting Florida and the Caribbean
The administration’s challenge is how to remove the regime without detonating the country.
Why Cuba Matters Strategically to the US
Beyond ideology, Cuba holds:
- Nickel and cobalt reserves
- Potential offshore oil and gas
- Control near key Caribbean sea lanes
- Proximity to US territory
US intelligence also highlights Cuba’s strategic location near the Windward Passage, vital to global shipping.
Trump’s Legacy Calculation
For Trump, ending Communist rule in Cuba would be historic.
It would:
- Close a Cold War chapter
- Succeed where JFK failed
- Cement dominance in the Western Hemisphere
One former official said:
“Trump believes this would define his foreign policy legacy.”
Conclusion: Is Cuba Really Next?
According to US officials and reporting by The Wall Street Journal, the Trump administration is actively preparing for a post-Communist Cuba — even if the path there remains uncertain.
The pressure campaign is real. The economic crisis is real. The warnings are explicit.
But Cuba has survived:
- Invasions
- Embargoes
- Sabotage
- Global isolation
Whether insider deals can achieve what decades of pressure could not remains an open — and dangerous — question.
Also Read: 13 Explosive Warnings as Trump Tells Cuba to ‘Make a Deal’ or Collapse
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