When are we going after Cuba?

We all saw Trump and Marco Rubio ramp up the heat recently by calling Cuba a failed country and targeting Raúl Castro. Trump even flat-out hinted that while previous presidents have spent sixty years looking at doing something about the island, he would be the one to actually finish the job. If the administration is genuinely planning a definitive move to collapse the regime, the clock is ticking loudly. This isn't a call for a military invasion, but rather a realization that if a final, decisive economic chokehold is coming, it has to happen before the midterm election cycle completely freezes major foreign policy wildcards.

The administration has already laid the groundwork this year with brutal secondary sanctions targeting Cuban banking and threatening massive tariffs on foreign nations that try to ship oil to the island. With Venezuela’s lifeline cut and the Cuban electrical grid in total collapse, the regime is completely vulnerable and on life support. However, the window for a knockout blow is rapidly closing because Washington always gets cautious as November approaches. If Trump wants to fulfill his promise to the Florida electorate and finally break the back of the Cuban dictatorship, he has a very narrow summer window to do it. If it doesn’t happen soon, the momentum will stall, and Havana will simply wait us out.