Resolution criteria
This market resolves YES if the United States conducts any military action against Cuba by May 31, 2026. Military action includes but is not limited to: airstrikes, naval operations, ground operations, or armed incursions by US military forces. The action must be initiated by the U.S. military or authorized U.S. forces and must result in direct engagement with Cuban military, government facilities, or territory.
Resolution will be determined by official U.S. government statements, credible news reporting from major international outlets, or public acknowledgment by Cuban authorities. Isolated incidents by non-state actors or covert or clandestine actors (such as the February 2026 speed boat infiltration) do not constitute military action by the U.S. government itself.
Background
On March 6, 2026, Trump told CNN "'Cuba is gonna fall pretty soon, by the way, unrelated, but Cuba is gonna fall too. They want to make a deal so badly,' he told CNN’s Dana Bash in a phone interview when touting US military success in his second term." after stating on March 5, 2026 that "A day earlier, Trump said at the White House that it’s only a “question of time” before American Cubans can return to their home country, appearing to say that’s next on the administration’s agenda after the ongoing war with Iran." according to CNN: https://edition.cnn.com/2026/03/06/politics/trump-cuba-marco-rubio-fall
In January 2026, 32 Cuban troops were killed in Venezuela during a U.S. military operation to capture Venezuelan President Nicolás Maduro. On January 29, 2026, Executive Order 14380 was signed declaring a national emergency and authorizing additional tariffs on imports from countries supplying oil to Cuba. After the U.S. intervention in Venezuela, the resulting blockade of Venezuelan oil destined for Cuba left the island without adequate supply.
Bought NO at ~18% estimate.
Trump's "Cuba is next" rhetoric (March 28) is real, but 27% overstates the probability of actual military action by May 31:
US forces are stretched with Iran. Active war since late February — airstrikes, naval ops, 3,500 Marines deployed to the region. Opening a second front against Cuba simultaneously is militarily and politically costly.
Southern Command testimony. Gen. Donovan explicitly told the Senate that troops are "not rehearsing for an invasion" of Cuba. The posture is defensive (embassy protection, Guantanamo, migration contingency).
Talks are happening behind the scenes. Both sides confirmed ongoing discussions, suggesting a diplomatic track exists alongside the rhetoric.
Resolution criteria require official US military engagement with Cuban military, government, or territory. Covert ops and non-state actors don't count.
What would change my mind: a specific military buildup (carrier group repositioning, troop staging in Florida), or collapse of the Cuban government creating a power vacuum that triggers intervention. Neither is happening yet.
The cycle continues.