Will Cuba Pay the Price for Trump’s Thwarted Hubris?

The American relationship with Cuba over the past century and a bit could charitably be described as complicated.

The island was ‘liberated’ from Spanish control following the Spanish-American War of 1898 though in reality the United States heavily circumscribed Cuban independence under the terms of the Platt Amendments (which allowed the US to intervene in Cuba if it so chose), turning the island into a de facto vassal. All of this was in keeping with the Monroe Doctrine and the United States’ desire for a sphere of influence in the western hemisphere. The opinions of the Cuban people, whose economy was integrated with and exploited by their gigantic neighbour, never really seemed to count for much.

And we all know how it turned out in the Cuban Revolution that brought Fidel Castro to power, in the disastrous Bay of Pigs intervention where the Americans supported an abortive invasion hoping to overthrow Castro (instead cementing his rule) and finally in the Cuban Missile crisis where the Soviet Union ultimately backed down BUT where Soviet leader Nikita Khruschev secured a promise from the then Kennedy administration that the United States would not invade Cuba.

And for the past sixty-plus years they haven’t, leaving Cuba intact as an anti-American communist state some 90 miles offshore from their own mainland. This bothers them. It has always bothered them. It clearly violates the instinct in Washington that they should be unchallenged in the Americas. The existence of the Cuban regime as it stands today is itself a provocation. And they would dearly love to ‘rectify’ that issue.

I have to add I am not portraying the Cuban regime as the good guys here. It’s a communist dictatorship that imprisons its critics and which has helped impoverish its own country. As with Iran, if that government collapses, I won’t shed any tears. But I also think that wiser US Presidents have been correct in seeing unsavoury regimes as problems to be carefully managed rather than indulging the cheap catharsis and ego-flattering nonsense of forcing the issue through a violent intervention that carries with it unforeseen consequences and the potential for immense human misery.

But many Americans aren’t willing to wait for the regime’s internal contradictions to bring it down. They wish to expedite things. Many of those who think this way can be found among the Cuban-American community based in southern Florida, consisting of exiles and the descendants of exiles who fled persecution under the Communist regime. They pine for the day a government they hate collapses.

The more muscular approach towards the island advocated for by Republicans have made them a reliably Republican voting bloc, one which has demonstrated its influence in the past. There are still those who believe the backlash against the decision of the Clinton Administration to repatriate Elián Gonzalez back to the custody of his father led to the election of George W.Bush at the turn of the millennium (as that election hinged on an impossibly small margin in the state of Florida) and all that has subsequently flowed from that outcome.

The Cuban-Americans demand hawks from their public representatives on the matter of their ancestral homeland.

And so enter Trump, only too happy to oblige.

Trump is not a happy man these days. He has overplayed his hand badly in regards to Iran. It’s been quite staggering to see how he has blown the overwhelming US advantage in power against the Islamic Republic by attacking that nation without considering the likely consequences of his actions. His hubris, fuelled by previously brazen actions taken during his second term in office that delivered successes without feared consequences, has finally caught up with him.

At this point the war could genuinely end as an American Suez Crisis and demonstrate the limits of American power to the wider world.

The American President knows this.

Beneath his bluster and arrogance lies a man keenly aware of, and enraged by, the negative opinions lobbed his way. To say he is thin-skinned almost seems to understate his inability to respond rationally to criticism. Such a person is almost by definition unfit for the Presidency, yet he is the President, and we all must endure the consequences of his misjudgments and petty retributions.

Though it seems increasingly likely the people of Cuba are going to endure those consequences more than most. Were it not for the fact that global geopolitics has gone haywire this year, what is currently happening in Cuba would likely be dominating the news right now.

Trump has effectively imposed a full blockade on the island, several steps up from the long-running embargo the United States imposed on the island from 1960 onwards.

According to Diana Roy, writing for the Council on Foreign Relations…

Since January, the Donald Trump administration has severely limited oil shipments to Cuba, a decision which has sparked fuel shortages, sharp price increases, and prolonged power outages—the country has already experienced three nationwide blackouts in March. Cuba’s recent economic and energy crises stem from a combination of long-standing structural challenges and policy decisions, including underinvestment in the energy sector, but Trump’s hard-line policies and economic sanctions have exacerbated these difficulties since he returned to office in 2025.

Senior U.S. officials have indicated that the end goal of these policies is to bring about political and economic liberalization in Cuba, including the potential removal of President Miguel Díaz-Canel from power. “Cuba has an economy that doesn’t work and a political and governmental system that can’t fix it. So they have to change dramatically,” said U.S. Secretary of State Marco Rubio on March 17. “They’ve got some big decisions to make over there.”

Cuba is currently experiencing the worst humanitarian crisis it has seen since the revolution as a result of Trump’s enforced embargo. Trump’s motives are transparent, as he said a few weeks back he feels that ‘he will have the honor of taking Cuba’.

This is about him trying to prove that he can accomplish with direct action what his predecessors, many of whom he regularly lambasts as ‘weak’ and ‘stupid’ for their preference of multi-lateral diplomacy rather than the direct application of American might, could not.

And in the aftermath of his ongoing humiliation in the Middle East, where his attempt to ‘solve’ that particularly long-running problem is instead looking like it is making everything worse, the temptation to put the squeeze on Cuba and to be the US President who removes a perpetual thorn in their side could very well prove to be too tempting for him to pass up.

In his mind he badly needs a win and Cuba is bound to look like a much easier target than Iran at this point. A violent intervention is already ongoing as inflicting a humanitarian catastrophe on an entire nation, as Trump has done, is an inherently violent act.

As to where this violent intervention will ultimately go, it looks like a full-scale invasion is unlikely. That would that require significant military assets to be committed to an invasion, assets the US can probably no longer afford to spend given their expenditures over Iran and as they try and keep one eye on an increasingly gleeful China.

Instead it seems Trump is angling for a more Venezuela-style approach. He’d likely prefer an internal coup that installs a US-friendly leader (there have been frequent reports that the Trump administration is ‘negotiating’ with Fidel Castro’s grand-nephew Rául Castro) given that would deliver him a win without the messy aftermath. If that’s not forthcoming, he may opt for a decapitation strike that is similar to the one that removed Maduro and, again, the installation of a US friendly leadership.

I fear Trump won’t back down on this. If he, somehow, pulls out a win over Iran then he will be emboldened. If he is forced into a humiliating compromise with Iran, no matter how he attempts to spin it, he will feel emasculated and desperate to reassert himself.

Either way, dark days probably lie ahead for Havana.