What Was the CIA Director Doing in Cuba?

I have to admit I was a bit shocked when scrolling through X to discover this post from the CIA. There were pictures, but without explanation. 

Havana, Cuba pic.twitter.com/7S7TtJPyf5

— CIA (@CIA) May 14, 2026

That’s CIA Director John Ratcliffe and folks whose faces are blurred out (likely active CIA assets), apparently meeting with Cuban officials. 

Here he is outside the U.S. Embassy in Cuba. That looks like he’s standing with Chief of Mission Mike Hammer.

. @USEmbCuba https://t.co/VSCtMdqQ6A pic.twitter.com/VNRWiqvSK6

— Embajada de los Estados Unidos en Cuba (@USEmbCuba) May 15, 2026

So what was Ratcliffe doing there, and why was the CIA posting about it? 

Turns out he was there to meet with Raúl Castro’s grandson, who is a colonel in the Ministry of Interior, who has acted as a gatekeeper/intermediary to his grandfather. 

Ratcliffe met with Raúl Guillermo Rodríguez Castro, Interior Minister Lázaro Álvarez Casas and the head of Cuban intelligence services, and discussed intelligence cooperation, economic stability and security issues. A CIA official confirmed the meetings to the AP.

Ratcliffe was there “to personally deliver President Donald Trump’s message that the United States is prepared to seriously engage on economic and security issues, but only if Cuba makes fundamental changes,’’ the CIA official said. 

An official statement from Cuba’s government noted that Thursday’s meeting “took place … against a backdrop of complex bilateral relations.”

You don’t generally think of the CIA Director performing in a diplomatic role. But actually that might also send a message too — as in, “Understand our capabilities — you don’t want to hit the ‘find out’ stage.”

According to the AP, Secretary of State Marco Rubio had a meeting with the same man in February during a Caribbean Community summit in St. Kitts, and U.S. and Cuban officials also met recently in Cuba.

Meanwhile, Cuba is in deep trouble because they no longer have the oil they were getting from Venezuela. They were already in big economic problems before that. And we’re turning the screws, with also reportedly seeking to indict Raúl Castro, their former leader. While Castro stepped down in 2018, he is still seen as an important figure in the Communist regime. 

The potential indictment — which would need to be approved by a grand jury — is expected to focus on Cuba’s deadly 1996 shootdown of planes operated by humanitarian group Brothers to the Rescue.

The plan comes as the U.S. heaps pressure on the Cuban government. The Trump administration has threatened heavy tariffs on any country that exports oil to Cuba, leading to energy shortages as oil shipments are largely cut off.

READ MORE: Raúl Castro’s Past Comes Knocking: U.S. Moves to Indict Cuban Revolutionary in Deadly ’90s Attack

This shows that, although President Donald Trump is in China, he’s still keeping the pressure on and making moves regarding Cuba.

It sounds like Ratcliffe might be there giving them their options, which, right now, don’t look good, without change. 

If the CIA is meeting with you face to face like this, your regime is already changed, you just don’t know it yet. https://t.co/Ak42RCyTEu

— Wall Street Mav (@WallStreetMav) May 15, 2026

HOY ME VOY A DORMIR FELIZ https://t.co/iEPJjEedy2

— Ramiro Marra (@RAMIROMARRA) May 15, 2026

That translates to, “Today, I am going to sleep happy.” 

Editor’s Note: Thanks to President Trump and his administration’s bold leadership, we are respected on the world stage, and our enemies are being put on notice.

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