The Trump administration is reportedly taking active steps towards orchestrating a political shift in Cuba before the end of the year, as detailed in an in-depth investigation by The Wall Street Journal.
According to U.S. officials cited by the publication, Washington perceives a "historical opportunity" to apply pressure on the Cuban government, pushing it to the brink of collapse amid unprecedented economic decline and increasing regional isolation.
Though there is no declared military agenda or official timeline, the White House's approach involves ramping up economic, diplomatic, and symbolic pressures on the Cuban regime while seeking internal partners open to negotiating a potential transition.
Covert Communications and Internal Alliances
In addition to public pressure tactics, the U.S. government has stepped up discreet communications with the Cuban exile community and civic leaders in cities like Miami and Washington.
The goal? To pinpoint potential figures within the Cuban state apparatus who "see the writing on the wall" and are prepared to negotiate a peaceful resolution.
As reported by the Journal, several private meetings have taken place, seeking information on Cuban officials or military personnel "ready to recognize the historical moment" and break away from the ruling elite.
An Economy on the Brink and the Loss of Venezuelan Support
U.S. intelligence assessments paint a bleak picture of Cuba: chronic shortages of essential goods, scarcity of medicines, prolonged power outages, and severe economic contraction.
This situation is exacerbated by the loss of Venezuelan support following the capture of Nicolás Maduro by U.S. forces on January 3, leaving Cuba without its main source of subsidized oil.
"Cuba seems ready to fall. I don't know how they'll sustain themselves; they have no income. They got all their income from Venezuela, from Venezuelan oil," President Trump recently stated during an interview aboard Air Force One.
The U.S. government believes this extreme weakening of the Cuban model presents favorable conditions for advocating a political exit.
Venezuelan Operation as a Warning Model
Trump administration officials acknowledge that the military operation in Caracas, which resulted in Maduro's capture and the deaths of at least 32 Cuban soldiers and agents, served as a "successful model" of covert action with informant participation from within the regime.
The Journal reports that the White House hopes to emulate a similar strategy in Cuba.
"Cuba's rulers are incompetent Marxists who have ruined their country," a senior White House official stated, emphasizing that "they must make a deal before it is too late."
This warning was also echoed on social media. On January 11, Trump posted on his platform Truth Social: "I strongly suggest they make a deal, BEFORE IT IS TOO LATE."
Economic Sanctions and Symbolic Penalties
Washington's strategy also involves toughening economic sanctions. Recent measures include:
- Migratory restrictions on Cuban officials linked to international medical missions, viewed by the U.S. as a form of state-imposed forced labor.
- Diplomatic pressure on countries hosting Cuban doctors to limit the program's reach.
- Threatening a complete oil cutoff through enhanced naval surveillance and pressure on potential alternative suppliers.
The State Department stated that it is in the strategic interest of U.S. national security for Cuba to "have a democratic government and not harbor military or intelligence services from adversary powers."
Havana's Response and International Support
From Cuba, Miguel Díaz-Canel has categorically rejected any negotiation under duress.
"There is no possible surrender or capitulation," he declared at a recent event.
The regime has also mobilized official demonstrations and messages of unity against what it describes as an "imperialist aggression."
Internationally, Russia has expressed its support for Havana, labeling Washington's strategy as "blackmail and threats," consistent with its strengthened geopolitical alliance with the island.
A Political Legacy for Trump and Florida Allies
According to the Journal, Trump views the end of the Cuban regime as a historical achievement in foreign policy.
Anti-Castro rhetoric has been a constant theme in his speeches, resonating with influential exiled Cuban sectors and key figures in his administration, like Secretary of State Marco Rubio.
"The anti-communist hawks in the administration have always felt that this place is so small and so close that it's a real humiliation to allow it to continue as it is," commented David Smith, a foreign policy expert at the University of Sydney, in an interview with Al Jazeera.
A Tougher Challenge than Venezuela?
Despite optimism in Washington, some analysts caution about the structural differences between Cuba and Venezuela. Ricardo Zúñiga, a former official in the Obama administration involved in the bilateral thaw between 2014 and 2017, noted: "The Cuban regime is a much tougher nut to crack."
Unlike Caracas, Cuba lacks an organized opposition or frequent protests that could fuel an internal negotiated exit.
Moreover, as Smith pointed out, the Cuban regime has survived six decades of sanctions, assassination attempts, diplomatic isolation, and deep economic crises.
The loyalty of the repressive apparatus and the opacity of internal power dynamics on the island remain barriers to any external attempts at causing a collapse.
The White House appears determined to play its most ambitious card in Latin America: to end Cuban communism, a feat that numerous U.S. presidents have not achieved.
As a Wall Street Journal source put it: "This is the moment. If we don't act now, we might not get another chance for decades."
Key Questions on U.S. Strategy Toward Cuba
What is the main objective of the Trump administration's strategy in Cuba?
The primary goal is to instigate a political shift in Cuba by applying economic, diplomatic, and symbolic pressures, while identifying internal partners open to negotiating a transition.
How has the loss of Venezuelan support affected Cuba?
The capture of Nicolás Maduro by U.S. forces has left Cuba without its main source of subsidized oil, exacerbating its economic crisis and increasing the government's vulnerability.
What are some of the economic sanctions imposed by the U.S. on Cuba?
Sanctions include migratory restrictions on Cuban officials involved in medical missions abroad, diplomatic pressure on host countries of Cuban doctors, and threats of a complete oil cutoff through enhanced naval surveillance.