Talk inside Washington suggests the Trump administration believes the political clock may finally be ticking for Cuba’s long-standing communist leadership.
According to US officials speaking to The Wall Street Journal, the White House is increasingly confident that a dramatic shift in Havana could happen before the end of the year, even though no official playbook for toppling the government has been publicly revealed.
Why the White House Thinks the Moment Is Ripe
Officials say two major developments have fueled this renewed confidence.
First is the recent US-backed operation that led to the capture and removal of Venezuela’s socialist leader, Nicolás Maduro, on January 3.
That success has emboldened some within the administration, who see it as proof that entrenched left-wing governments in the region are not untouchable.
Second, Cuba’s economic lifeline has been deeply tied to Venezuela for years, particularly through heavily subsidized oil supplies.
With Maduro now out of power, US intelligence analysts believe Cuba’s already fragile economy is on the brink of collapse.
An Economy Under Extreme Strain
Intelligence assessments paint a bleak picture of daily life on the island.
Widespread blackouts, shortages of food and medicine, and extreme poverty have become the norm.
Nearly nine out of ten Cubans are said to be living below the poverty line, while oil supplies are expected to dry up within weeks if alternative sources are not secured.
US officials believe this mounting hardship could create cracks within the Cuban leadership, even if it doesn’t immediately spark mass unrest.
No Invasion Plan, but a Search for Insiders
Despite the bold rhetoric, officials stress there is no concrete military plan to overthrow Cuba’s government, which has ruled since Fidel Castro seized power in 1959.
Instead, the current focus is quieter and more strategic: identifying figures inside the Cuban system who may be open to cutting deals with Washington.
This approach closely mirrors how the operation against Maduro unfolded, where someone from within his inner circle ultimately turned against him.
That mission culminated in a dramatic assault on Caracas, costing the lives of dozens of Cuban soldiers and members of Maduro’s security team.
Oil as a Weapon of Pressure
Alongside diplomatic maneuvering, the US is intensifying economic pressure.
By targeting oil shipments tied to Venezuela, American forces are not only punishing Caracas for past policies but also tightening the screws on Havana.
For decades, Venezuelan oil has kept Cuba’s lights on, and cutting it off now threatens to bring the island’s economy to a grinding halt.
Sharp Divisions Inside the Administration
Not everyone in Trump’s orbit agrees on how far to push.
Some officials and close allies—particularly Cuban exiles based in Florida—are urging a hard-line approach to finally end nearly 70 years of communist rule.
Others are urging caution, pointing to past failures like the Bay of Pigs invasion and the long-running trade embargo, both of which failed to dislodge the Castro leadership and instead entrenched it further.
Why Cuba Isn’t Venezuela
Skeptics inside the administration argue that Cuba presents a far tougher challenge than Venezuela ever did.
Cuba operates as a strict single-party state, bans political opposition, and has violently crushed the few large-scale protests it has faced, notably in 1994 and again nationwide in 2021.
Venezuela, by contrast, has had visible opposition movements, recurring protests, and elections—even if those elections were widely viewed as rigged to keep Maduro in power.
Fears of Chaos and Humanitarian Fallout
Some Trump officials worry that trying to replicate the Venezuelan playbook in Cuba could backfire badly.
With citizens already heavily repressed and resources scarce, a sudden collapse could trigger a major humanitarian crisis, destabilizing the island and potentially sending waves of refugees abroad.
Legacy on the Line for Trump
Despite the risks, Trump reportedly sees the potential end of Castro-era rule as a defining foreign policy achievement.
Advisors say he believes succeeding where past presidents—including John F. Kennedy—failed would cement his legacy in the Western Hemisphere.
Public Warnings and Defiant Responses
The administration has become increasingly open about its intentions.
Jeremy Lewin, the State Department’s acting undersecretary for foreign assistance, recently said Cuba must either step aside or find a way to genuinely provide for its people.
Trump himself escalated the message on January 11, warning that after Maduro’s fall, no more Venezuelan oil or money would be flowing to Havana.
He urged Cuban leaders to strike a deal “before it is too late.”
Havana Shows No Sign of Backing Down
So far, Cuban leaders appear unmoved.
Power still rests heavily with Raúl Castro, now 94, even after he formally stepped aside in 2021 and handed day-to-day leadership to President Miguel Díaz-Canel.
Díaz-Canel recently dismissed US pressure outright, declaring that Cuba would not surrender or negotiate under coercion, especially while honoring Cuban security personnel killed during efforts to protect Maduro.
What Comes Next?
With economic pressure mounting, diplomatic warnings growing louder, and internal debates still unresolved, the path forward remains uncertain.
Whether this moment leads to historic change—or becomes another failed chapter in US-Cuba relations—is a question that may soon have an answer.
Share on Facebook «||» Share on Twitter «||» Share on Reddit «||» Share on LinkedIn