A U.S. Department of Justice official told Reuters on May 14 that the indictment of Raúl Castro "sounds imminent." The official, speaking anonymously, said the action is happening soon.

Grand jury approval is still required. But the machinery is moving.

The Ratcliffe Trip

CIA Director John Ratcliffe flew to Havana on May 14 — an unusual move — and sat down with Raúl "Raulito" Guillermo Rodríguez Castro, the 94-year-old's grandson, along with Interior Minister Lázaro Álvarez Casas and the head of Cuban intelligence services.

Ratcliffe delivered Trump's message directly: the U.S. will engage on economic and security issues, but only if Cuba makes fundamental changes. A CIA official confirmed Cuba can "no longer be a safe haven for adversaries in the Western Hemisphere."

You don't fly the CIA director to a communist adversary's capital for a goodwill visit. You do it to deliver a warning with a smile.

The 1996 Case

On February 24, 1996, Cuban Air Force MiG-23 fighter jets shot down two unarmed Cessnas operated by Brothers to the Rescue — an exile humanitarian group that patrolled the Florida Straits looking for Cuban rafters.

Four people were killed.

The International Civil Aviation Organization (ICAO) concluded the planes were shot down outside Cuban airspace — meaning Cuba violated international law. The U.S. Congress later found the planes were on a mission identical to hundreds they'd flown since 1991 and posed no threat to Cuba.

At the time, Raúl Castro was Cuba's Defense Minister and commanded the armed forces. The U.S. Southern District of Florida has been building a prosecutorial initiative for months targeting Cuban Communist Party leadership specifically, according to CBS News.

The Broader Pressure Campaign

Reuters flagged the Venezuela parallel that deserves attention: in January, the Trump administration called its military operation against Nicolás Maduro a "law enforcement operation" to execute criminal charges. Trump said in March that Cuba is next.

The oil blockade, the power outages, the expanded sanctions, the CIA visit, and the imminent indictment are all part of one coordinated strategy.

Miami's Federal Prosecutors

According to CBS News, Miami's top federal prosecutor launched a dedicated initiative months ago targeting Cuban communist leaders. It involves federal and local law enforcement plus the U.S. Treasury Department and covers economic crimes, drugs, violent crimes, and immigration violations.

Raúl Castro stepped down as Communist Party leader in 2021. He's 94 and hasn't held formal power in years. But he's still widely considered one of the most powerful figures on the island, and his grandson is the regime's point of contact with Washington.

Indicting the patriarch signals to every Cuban official still in power: we know who you are, and we have grand juries.

The Implications

For the four families who lost loved ones when Cuba shot down those planes in 1996, this comes 30 years after the fact.

For Cubans on the island right now — already suffering blackouts, fuel shortages, and food scarcity from the U.S. blockade — the pressure is about to intensify.

For the Castro regime, the math is simple: Ratcliffe flew to Havana with a carrot and a stick. The carrot is economic engagement. The stick is a federal indictment of the man who built the entire security apparatus.

The Trump administration has used criminal charges to build pressure against adversaries in the region. They're building the same case file on Cuba.