Another Sign the Cuban Regime's Days Are Numbered

AP Photo/Desmond Boylan

Everyone is focused on Iran right now and appropriately so, but we're still watching event in Cuba closely. President Trump suggested this week that Cuba's government was going to collapse and that Sec. of State Rubio had been talking to people there about a future deal. However, the president said he wanted to remain focused on Iran for a couple more weeks.

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“We want to finish this one first,” Trump said Thursday, referring to the current attack on Iran. It “will be just a question of time” before Cuba’s government falls, and “you and a lot of unbelievable people are going to be going back to Cuba, hopefully not to stay,” he told a White House audience that included a large number of Republicans from South Florida, many of Cuban descent.

“I just want to wait a couple of weeks,” he added. On Friday, in an interview with CNN, he repeated that Cuba “is going to fall very soon.”

Today there's a fresh sign that the administration is in fact doing two things at once. The DOJ is now actively investigating Cuba's communist leadership with the goal of bringing indictments.

The U.S. attorney in South Florida has ordered a broad-ranging inquiry into Cuba’s leaders and Communist Party officials for drug, immigration, economic and violent crimes with a goal of bringing fast indictments, according to three people with knowledge of his actions...

Bringing criminal cases against Cuban leaders could provide a legal and political pretext for...action, just as the Justice Department’s indictment against Venezuela’s president, Nicolás Maduro, and his wife, Cilia Flores, was used to justify his capture and extradition.

Leading the new effort in Florida is Jason A. Reding Quiñones, a relatively inexperienced federal prosecutor and Trump loyalist...

If the administration does in fact seek charges against Cuba’s leaders to facilitate a snatch-and-grab operation inside Cuba like that against Mr. Maduro, it would be an extraordinary use of the criminal justice system to advance the White House’s geopolitical agenda. Federal indictments are not typically meant to be a pretext to remove foreign leaders from office, but rather to bring them to justice inside American courts.

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Last month, Cuban American members of congress asked Trump to pursue indictments against Cuba, and specifically against Raul Castro, for the shooting down of two airplanes in 1996.  Mario Diaz-Balart, Carlos Gimenez and Maria Elvira Salazar and Nicole Malliotakis argued Castro was directly responsible for this attack.

It is our understanding, based on public information, that on February 24, 1996, Raul Castro ordered a Cuban Mig fighter jet to engage and obliterate two Brothers to the Rescue civilian aircraft over international waters. Flying those planes were three American citizens, Armando Alejandre, Jr., Carlos Costa, Mario de la Pena and Pablo Morales, a legal U.S. resident. Those four brave men were flying small civilian aircraft over the Straits of Florida to identify and help rescue Cuban rafters making the perilous escape from totalitarian Cuba. We believe that the following facts are instructive regarding Raul Castro’s complicity in the crime...

In an audio recording of a conversation which took place just weeks after the shooting and obtained by The Miami Herald, Raul Castro can be heard discussing giving the orders to shoot down the Brothers to the Rescue aircraft: In the recording, Raul Castro can be heard saying: “I told them [Cuban Mig pilots] to try to knock them down over [Cuban] territory, ”and “Knock them down into the sea when they reappear.”

Raul Castro isn't in control of Cuba at this point, he's 94-years-old, but as the surviving link to Fidel Castro's legacy, dragging him into an American court would be a statement about the island's future.

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And there could be other indictments against other leaders, maybe even Cuba's current president Miguel Díaz-Canel. What both the NY Times and the Washington Post see coming is another special forces operation that simply removes the leadership and replaces it with someone willing to play ball with the United States.

The effort to bring charges against Cuban officials coincides with President Donald Trump saying that his administration is eyeing Cuba as the next country whose government might be overthrown, following the capture of Venezuela’s Nicolás Maduro in early January and the killing of Iran’s supreme leader last Saturday.

This may be what Trump has in mind. We'll have to wait a few more weeks to find out.

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Mitch Berg 4:25 PM | March 06, 2026
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