Trump sets his sights on Cuba

There’s a real Netflix energy to geopolitics coverage right now — Maduro gets yeeted, and within hours everyone is frothing over season two (Cuba).

So… is Cuba next? Let’s find out.

In the spirit of casually summarising seven decades of US-Cuba history in a paragraph already part-wasted on throat-clearing, the TLDR is there’s been bad blood since Fidel Castro’s communists ousted the unpopular Batista administration, seized ~6,000 US-owned firms, executed ~1,000 political rivals, arrested tens of thousands more, and sent another quarter million folks fleeing in the initial exile wave alone.

It’s been intrigue ever since, with the US trying everything from the disastrous Bay of Pigs invasion, endless assassination plots, and modern history’s longest-running embargo, while Cuba has deployed tens of thousands of troops around the world, hosted Soviet nukes a jet-ski away from Miami’s beaches, and locked up its own people for suggesting that, you know, maybe they’d like a say in how their country is run. Cuban intelligence is strong, too, managing to recruit (say) deep in the DIA, and even a US ambassador.

And that brings us to Trump 2.0, who’s now ramped up pressure by… 

• Seizing Venezuela’s Nicolás Maduro and cutting Havana’s cheap oil
• Pressuring Mexico to halt its own oil shipments, and
• Threatening tariffs on anyone else supplying Cuba with oil.

The result is the island of 11 million people just ran out of jet fuel, and has maybe 20 days of regular fuel left until life grinds to a halt: transport, agriculture, tourism, food distribution, and hospitals potentially going dark as Cuba’s blackouts go permanent.

Why? It’s the Donroe Doctrine of US pre-eminence in the region, and Trump’s gambit is Cuba’s leaders will do a deal: maybe prisoner releases, compensation for seized US assets, and/or cutting security ties with Russia and China, which both run big signals intelligence facilities out of Cuba targeting the US (which of course spies back). DC hardliners like Marco Rubio, born to Cuban émigrés, also want more: regime change.

So… is Havana caving? Not yet. Hardly a stranger to US pressure, it’s adapting instead, with new restrictions on fuel sales, plus a four-day work week for state employees — the idea is to reduce energy consumption so forex-generating activities like tourism can continue off Cuba’s own heavy oil output (covering ~40% of its energy needs).

And… will Havana cave?

To be clear, this is shaping up as Cuba’s biggest threat since the 1991 collapse of its key sponsors (the Soviets), and it was already under pressure via (say) rare 2021 protests or an unusually public and senior corruption scandal involving the economy minister in 2025.

Plus if Maduro’s fate is any guide, it’s hard to see China or Russia doing much beyond their current offers of food and oil, in yet another reminder of the regional limits of their own power, not to mention Cuba’s own isolation. Meanwhile, Maduro’s fate was also a reminder of not just US power, but Trump’s willingness to use it.

That being said, this island’s regime has proven resilient through decades of crises, retains tight control over society, has a pervasive intelligence network, and broader security services with strong economic incentives to hold on. Ditto, its repression has prevented any real opposition from even coming close to gaining traction.

So all that to say… Cuba is no Venezuela: any hit would be higher-risk, while any leader swap would be lower-reward. That’s why a continued economic squeeze seems more likely for now. And yet to the extent this just creates even more misery on the island, that’ll further complicate DC’s calculations around what (if any) hand to play next.

Intrigue’s Take

We once happened to be standing near a US president (Obama) when several senior Latin American officials came over to greet him. They had maybe 30 seconds with the world’s most powerful man before his motorcade whisked him out of their lives, and do you know what they did with those 30 seconds? They didn’t even mention their own countries let alone some specific irritant. Rather, they thanked him for easing US pressure on Cuba.

And to be clear, these weren’t chardonnay socialists (known locally as ‘caviars’). To the contrary, they were staunch critics of disastrous authoritarians elsewhere, like Maduro.

Our point in mentioning this anecdote? Cuba enjoys an amount of quiet diplomatic goodwill that’ll be surprising for anyone reared on US soundbites. And that goodwill stems not from elections, competence, or even affinity, but rather a historical narrative that’s widely accepted, particularly (but not exclusively) across broader Latin America.

It’s the narrative that Cuba alone proves you can just say “no” to Washington. It’s this same narrative that’s allowed the regime to frame itself as the noble victim of imperialism rather than (say) the chief architect of its own misery. And it’s the same narrative that also helps explain why Havana now has one of the world’s highest embassy densities.

All that to say, this narrative won’t save Cuba’s communist party from whatever may come. But it will explain why the region’s reaction will be a little more mixed.

Sound even smarter:

• Two Mexican navy ships are on their way to the island carrying over 800 tons of initial humanitarian aid.
• Havana-friendly Nicaragua just ended its visa exemptions for Cubans, ending a popular escape route for folks hoping to flee Cuba for the US.
• Most nations vote against the US embargo on Cuba at the UN each year.