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The Trump administration has assessed Cuba’s economy as being close to collapse and that the government has never been this fragile after losing a vital benefactor in Venezuela Maduro
The Donald Trump administration is actively searching for government insiders within Cuba who could help broker a political deal to usher out the island’s Communist leadership by the end of the year, according to a Wall Street Journal report that frames the effort as a post-Venezuela strategic push.
Washington sees Cuba as next geopolitical battleground
Senior US officials told the Journal that, emboldened by the ouster of Nicolás Maduro in Venezuela, the administration believes Cuba’s long-standing communist regime is more vulnerable than at any time in decades and may be ripe for political transformation.
Officials cited in the report assessed that the collapse of Cuba’s key economic partner — Venezuela — has left Havana exposed, placing unusual stress on its economy. Although there is no detailed blueprint for ending Communist rule, the strategy being pursued involves identifying potential reform-minded figures inside the existing government who might be willing to negotiate a transfer of power.
Trump publicly urges negotiation ‘before it is too late’
In a Jan. 11 social-media post, Trump appeared to underscore this approach, exhorting Cuban leaders to seek an agreement with the United States.
“I strongly suggest they make a deal. BEFORE IT IS TOO LATE,” Trump said, adding that there would be “NO MORE OIL OR MONEY” channelled to Cuba.
The president’s hard-line stance follows a broader tightening of economic and diplomatic pressure on the island, including curbs on overseas medical missions — a critical source of hard currency for Havana — and visa bans on officials linked to those programmes, according to officials.
Lessons from Venezuela drive policy thinking
US officials told the Wall Street Journal that the January 3 operation in Venezuela — which resulted in the capture of Maduro and the death of allied Cuban security personnel — illustrates the perceived value of engaging with insiders to effect regime change. In Venezuela’s case, the raid was reportedly aided by an asset within the former president’s inner circle, reinforcing the administration’s belief in leveraging internal dissent or pragmatism as a catalyst for political transition.
In meetings with Cuban exile groups and civic leaders in Miami and Washington, U.S. officials have focused on identifying individuals within Havana’s ruling establishment who might “see the writing on the wall” and be willing to cut a deal rather than cling to power amid mounting economic strain, one official told the Journal.
Havana under strain but resistance remains
The Trump administration’s calculations are grounded in stark assessments of the Cuban economy, which has suffered chronic shortages, power blackouts and falls in oil supply since Caracas reduced exports and U.S. sanctions tightened. Analysts and residents alike have warned of deepening hardship, raising questions about the island government’s resilience.
Yet Cuban leaders have publicly rejected U.S. pressure. Tens of thousands of Cubans recently held a mass demonstration in Havana to denounce U.S. actions in Venezuela and protest Washington’s tightening sanctions, with President Miguel Díaz‑Canel affirming the government’s resolve.
International responses have also emerged. On 15 January, Reuters reported that Russia criticised what it described as “blackmail and threats” against Cuba, asserting that such approaches are unacceptable and reaffirming Moscow’s support for Havana.
Strategic gamble or overreach?
Trump and his advisers, including key figures with strong ties to Florida’s Cuban-American community, are treating the potential collapse or negotiated exit of Cuba’s Communist regime as a defining test of their hemispheric strategy. By leveraging diplomacy with insiders and continued economic pressure, they hope to achieve a peaceful but definitive end to communist rule without direct military intervention.
Yet analysts caution that such transitions are complex and can defy straightforward replication. Cuba’s centuries-old revolutionary government retains deep institutional control and popular symbolism, making any negotiated regime change a fraught proposition.
English (US) ·