Donald Trump’s regime change playbook is entering its third chapter, even as the second chapter is still being written, rewritten and resisted in real time.
What began in a compound in Caracas, Venezuela – a path forged in darkness by American special forces and presidential ambition – wound its way to Tehran. Now, increasingly, it appears to be leading towards Havana, Cuba.
First came Venezuela: the extraordinary raid which removed Nicolás Maduro from power and transported him to the United States, where he entered the same prison that once housed figures like Jeffrey Epstein and Sean Combs.
Then came Iran: a war launched with the language of speed and decisive victory, but which instead exposed the dangers of strategic overconfidence and a White House often bouncing between maximalist rhetoric and improvised diplomacy.
Now, the signs are gathering around Cuba.
The clearest signal – though far from the only one – came this week with the unsealing by the US Department of Justice of an indictment against Cuba’s 94-year-old former president, Raúl Castro, accusing him of murder linked to the shooting down of military aircraft decades ago.
In isolation, the case would already have represented a serious escalation in tensions between Washington and Havana. But in the context of Trump’s increasingly muscular policy towards the island, it has become clear that Cuba is the next destination for an American operation – of some sort or another – designed not merely to pressure a government but ultimately to destabilise or remove it.
Even the symbolism was striking. The indictment was unveiled on 20 May — a date celebrated in Cuba as marking the birth of the republic. Perhaps coincidence. Probably not.
Cuba and Trump caps on sale in Miami hours after federal US prosecutors announced charges against former Cuban president Raúl Castro (Photo: Rebecca Blackwell/AP)Around the same time, the aircraft carrier USS Nimitz sailed into the southern Caribbean, a deployment widely interpreted as another layer of pressure on the Cuban regime.
In truth, the signs of Trump’s intentions towards Cuba have been visible for months. The US has tightened sanctions, intensified efforts to restrict oil supplies to the island and pursued an economic pressure campaign severe enough to deepen fuel shortages and wider instability.
In another political era, developments like this might have dominated headlines. But in the permanent turbulence of Trump’s America – where crises collide and disappear within hours – some of these major strategic shifts have struggled to command attention for even one news cycle.
Their consequences, however, remain very real.
Cuba’s already fragile economy has deteriorated further, while fears of shortages and unrest have grown sharper. And just in case Trump’s intentions were not clear enough, he has personally floated the idea of a “friendly takeover” of Cuba – a phrase many dismissed as characteristic provocation from a president whose rhetoric often blurs the line between policy, performance and outright threat.
For Trump, a victory in Cuba – whatever form it ultimately takes – would represent more than a short-term political win. Unlike regime change in Tehran, or even Venezuela, a transformation in Havana would amount to an expansion of US influence in North America, likely to satisfy the same instinct for territorial and geopolitical assertion that lay behind his fascination with Greenland.
And for Trump’ Secretary of State, Marco Rubio, the issue appears even more personal.
He is the son of Cuban immigrants and has built much of his political identity around Cuba and opposition to its communist government. For years, Rubio has argued that Havana represents not merely an ideological adversary but a direct strategic challenge to the United States. It is he who increasingly appears to be driving the Trump administration’s enthusiasm for regime change on the island. Earlier this week he again described Cuba as a US “national security threat”.
US Secretary of State Marco Rubio, left, has described Cuba as a ‘national security threat’ to America (Photo: Jim Watson/AFP)How Trump’s failings in Iran could influence his Cuba strategy
A so-called “friendly takeover” of Cuba could be interpreted in several ways: economic coercion, internal destabilisation, negotiated capitulation or something far more direct. Asked this week about the possibility of using US forces to extract Castro from Cuba, Trump replied, ambiguously: “I don’t want to say that.”
But what might once have sounded like an implausible, even absurd idea now seems the obvious option, given the success of the US operation in Venezuela. Dangled threats against the US’s enemies have increasingly become the operating pattern of Trump-era power projection. Venezuela proved that. Iran reinforced it.
And yet, Iran also exposed US limits.
The operation there has plainly not unfolded as Washington imagined. Two and a half months after Trump declared the mission “very complete, pretty much”, it remains anything but complete.
The swift victory once implied by the White House has instead given way to something far murkier. Negotiations in Islamabad failed to produce the breakthrough American officials had hoped for, while attempts to secure an exit through backchannel diplomacy have also faltered.
There are lessons here for Washington. For all the precision weapons, satellite intelligence and technological superiority of modern warfare, conflict still obeys an older rule: wars are often far easier to begin than to end.
Solving the perceived “Cuba problem” offers Trump the chance to turn the attention economy back in his favour. But even for a President instinctively drawn to the momentum of the immediate news cycle, the stakes now appear larger than spectacle alone.
Nearly two years into a second term, facing low approval ratings at home and the growing prospect of strategic failure in Iran, the possibility of delivering a dramatic foreign policy victory much closer to US shores carries obvious appeal. A successful reshaping of Cuba would not only help consolidate support in the present but would offer Trump the prospect of defining his legacy around the restoration and expansion of American influence in its own hemisphere.
While keeping all options open on Cuba, it seems clear that Washington’s hope is that pressure from within leads to the collapse of the government there and a new, America First-friendly leadership to replace it. This might well rely on patience from a notoriously impatient US president.
What also remains unclear is whether Washington intends to wait for some form of resolution in Iran before turning fully towards Cuba — or whether escalating pressure on Havana is part of a more urgent attempt to reassert momentum more broadly from the White House.
But to argue, as some do, that Cuba would serve purely as a distraction from Iran – the way that many commentators saw that war as a diversion from the scandal of the Epstein files – risks understating the scale of the administration’s ambitions.
Because the truth may be simpler than that. Indeed, the evidence suggests that for the Trump administration, sooner or later, the path from Venezuela was always going to lead to Havana.
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