Is Cuba Next? Yeah, But Don’t Hold Your Breath…
- Ross Bogen
- 3 days ago
- 3 min read

By Club Member Ross Bogen
Jon Lee Anderson’s article, in the March 30 New Yorker, is packed with insights on the most likely next foreign policy outrage/excursion by the Trump administration, the toppling of the “Revolutionary” regime in Cuba and its absorption as an economic dependency into the developing american Co-Prosperity Sphere. Admittedly, it is a bit of a long read, even by New Yorker standards (over 7000 words), so while it’s well written and worthwhile, here’s the gist:
In a situation almost unthinkable 18 months ago, Anderson suggests that the Cuban government in is unlikely to survive the tender mercies of the U.S. now focused on them. The current situation in Venezuela and Iran could also have been called unthinkable, of course. As far as regime change goes, however, the third time may be the charm.
The problem is, while Venezuela could be called a failing state, Cuba makes it look practically thriving. Even before the US cut off oil supplies from Venezuela and imposed a virtual blockade, Cuba was effectively on life support. All the progress made recovering from the fall of the Soviet Union, during the Hugo Chavez years and the diplomatic/economic opening by the Obama administration, evaporated as Maduro reduced support and Trump restarted the Cold War. With its government essentially broke, infrastructure decimated by three hurricanes, tourism cut off by COVID, and recurring energy shortages, Cuba’s economy is comatose. In the last five years, the island has lost 20% of its population to emigration, including an even larger proportion of young people.
As shocking as it sounds, Venezuela’s fate seems almost hopeful to many Cubans. After all, the U.S. didn’t so much change Venezuela’s regime as co-opt it, exacting tribute in the form of oil, but promising at least more stability. Unfortunately for Cuba, it doesn’t have a singular leader available for decapitation, even figuratively, or a stand-in comparable to Delcy Rodriguez. Its natural resources are limited to some minerals (no oil), and tobacco, but mainly sand – that is, beaches. While El Trump Habanero is a possibility, the governance vacuum and decrepit infrastructure – “crumbling” would be generous – pose serious obstacles. The amount of investment necessary simply to re-establish a functioning economy is staggeringly huge.
Given its current pre-occupation (so to speak) with Iran, Anderson suggests the US is unlikely to take military action in Cuba, instead trying “to choke it into submission”. Lest that descend into humanitarian crisis, Trump raised the proverbial boot off Cuba’s neck a bit this week by letting a Russian tanker through the blockade, giving the Cubans a few more weeks to think about it.
In the end, however, it’s hard to see how this will turn out well. Cuba has been under one-party, uncompromisingly communist rule for so long, it’s hard to imagine where a regime acceptable to the White House would come from. Instead, a distinct possibility is a descent into end-stage state failure, hopefully not a hellscape à la Haiti, and more likely a kleptocracy on the Russian model (a post-Communism trailblazer), with perhaps a Caribbean flavor added by the military taking the role of Haitian gangs. Anderson offers no predictions, for his part, only the observation that, between the self-interest of both the Americans and the current regime’s elite, the suffering of the Cuban people is only likely to increase.




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