Tipsheet

The CIA Lands in Havana: Trump Sends a Direct Message to the Cuban Regime

Dmitri Bolt
Dmitri Bolt  |  May 15, 2026 2:00 PM

CIA Director John Ratcliffe visited Cuba on Thursday to deliver a message that the island can no longer serve as a safe haven for America’s adversaries. 

The trip comes as President Trump continues to operate under what many have dubbed the “Donroe Doctrine,” a fusion of the Monroe Doctrine and the president’s name, which holds that the world’s most powerful nation should ensure that countries within its hemisphere are not acting against American interests. The visit also signals that the Trump administration may be weighing stronger action against Cuba if its demands are not met, similar to its approach toward Venezuela, as U.S. officials have not been particularly shy about calling for regime change in Havana.

The CIA director met with Cuba’s interior minister, the head of Cuban intelligence, and the grandson of Raúl Castro, and told them the United States is open to economic and security negotiations, but only if Cuba guarantees it will no longer serve as a safe haven for America’s adversaries.

The country has been facing a major crisis not only because of its communist government, but also because U.S. sanctions have blocked it from receiving oil from Russia and China, contributing to severe energy shortages and rolling blackouts.

The Cuban regime promptly denied that the U.S. had offered aid, although Secretary of State Marco Rubio revealed that the offer of $100 million to the country had been made both privately and now publicly. 

This comes as the Trump administration views Cuba as the next major target in the Americas to ensure alignment with U.S. interests.