President Donald Trump signed an executive order last Thursday that authorizes tariffs against any country supplying Cuba with oil. The goal is straightforward: cut off alternative suppliers like Mexico and Russia, and squeeze the island until something breaks.
The timing matters. After Venezuelan leader Nicolás Maduro was captured in January, Cuba lost its primary source of subsidized oil. The island's economy is teetering near collapse, and oil supplies are running dangerously low. Trump's team is reportedly already identifying Cuban exiles, government insiders, and civic groups to broker a deal that could replace the Communist leadership before the year ends.
What the Betting Markets Are Saying
Over on Polymarket, traders are pricing in a real possibility of regime change. The current odds that Miguel Díaz-Canel is out as Cuba's leader by December 31 sit at 55%. Meanwhile, the probability of a U.S. military strike on Cuba in that same timeframe is much lower at 26%.
That spread tells you something important: traders think Trump's economic pressure campaign could work without sending in troops. If a negotiated transition happens, both sides will come to the table with clear needs. The U.S. will want political concessions. Cuba will want economic relief. And one of the fastest ways to deliver that relief? Reopening tourism, starting with cruise ship itineraries.
Why Cruise Operators Are Paying Attention
For investors in Norwegian Cruise Line Holdings (NCLH), Royal Caribbean (RCL), and Carnival (CCL), a reopened Cuba could be a genuine game-changer.
U.S. cruise ships were last allowed to sail to Cuba during a brief normalization period from May 2016 to June 2019. Interest was massive. Then the Trump administration banned the routes again, and that was that.
Fast forward to today, and the cruise industry is dealing with what analysts are calling a "Caribbean Capacity Overhang." Regional capacity has jumped 9% year-over-year, creating a supply glut that's putting pressure on pricing power. Over 200 ships now operate in the Caribbean, and popular ports like Nassau are oversaturated. Maintaining premium pricing in that environment is tough.
Cuba could change the equation entirely. Between 2016 and 2019, Cuba sailings commanded pricing premiums roughly 20% higher than comparable cruises to the Bahamas. A democratic transition could reopen one of the most desirable and profitable destinations in the region, giving cruise lines a fresh itinerary option right when they need it most.
Whether Díaz-Canel actually loses power this year is anyone's guess. But the fact that prediction markets are pricing it above 50-50 suggests the pressure campaign is being taken seriously. And if Cuba does reopen, the cruise lines won't be the only ones watching closely.
