Trump Havana Hotel and Casino?

I worry that the next step will not be Greenland, but rather Cuba. I’m not sure that’s much better, although probably quite a lot less likely to shatter NATO.

The Cuban economy is under extraordinary pressure, suffering from aggressive trade and financial sanctions from the Trump administration and decades of economic mismanagement. 

The economy has contracted by 4% over the last year and is facing massive shortages of energy and food. 

Tourism to Cuba suffered mightily during the pandemic and has not recovered, just as additional financial sanctions have straitjacketed Havana’s efforts to access international financial markets.

Ending Venezuelan support for Havana will only exacerbate these conditions.

Cuba’s military defenses are trivial. While formidable during the Cold War, Cuba’s military capabilities rapidly atrophied in the 1990s and have not recovered. 

Estimates suggest that Cuba has fewer than two dozen active fighter aircraft, all of which are antiquated. The lack of hard cash and the need to fund domestic priorities shrank Cuba’s arms imports, with no replacement from local industry.

In short, Cuba would pose even less military menace to US intervention than Venezuela. 

Cuba is in a really bad way, probably worse even than in the 1990s after the collapse of the USSR. There’s not really a light at the end of the tunnel; the 2026 midterms offer no meaningful hope to change Trump’s foreign policy, and January 2029 is a long way off. Trump may not control Venezuela but deterring Caracas from supporting Havana is not a difficult thing to do. Any support from Russia or China would offer Trump an immediate casus belli. Moreover, despite his protestations I suspect Trump finds “solving” the Cuba “problem” to be an attractive part of his legacy. He’s no doubt watched the Godfather II many times, and would like to do what Hyman Roth (and John F. Kennedy) could not; create real partnership between government and “legitimate business.”

People have been going broke betting against the communist government of Cuba for longer than I’ve been alive… but there comes a time for us all and I think we’re running right up against it. The best I can say is that taking Cuba off the board would reduce just a little bit of the insanity of American politics… but that’s not much succor.