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Cuba could experience freedom for ‘first time in 70 years’ within weeks, former Trump official predicts
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Cuba could experience freedom for ‘first time in 70 years’ within weeks, former Trump official predicts

Jimmie Dempsey
Last updated: March 17, 2026 6:25 pm
Jimmie Dempsey Published March 17, 2026
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A former Trump administration official said the U.S. may be on the verge of a breakthrough in Cuba, as President Donald Trump ramps up “maximum pressure” on the island’s communist regime.

“I think where we could actually end up in the next couple of weeks is, for the first time in 70 years, we could have an opportunity for the Cuban people to actually experience freedom brought to them by Donald J. Trump,” former White House NSC chief of staff Alex Gray said Tuesday.

Appearing on “America’s Newsroom,” Gray contrasted Trump’s “maximum pressure” approach to the policies of previous administrations he says “strengthened the regime” and lengthened its tenure for another decade.

FLORIDA LAUNCHES PROBE AFTER CUBA KILLS 4 ABOARD US-FLAGGED SPEEDBOAT NEAR KEYS

“I think the ideal situation is that President Trump is able to do what his predecessors were not able to, which is to get Cuba to change its behavior long term and change its regime, and I think that the president is looking at the same set of facts that previous American presidents looked at, and they didn’t do anything with it,” Gray told Dana Perino.

“Barack Obama looked at an opportunity in the 2010s and… he opened a U.S. Embassy there. He actually strengthened the regime and kept it on life support for another decade.”

CUBAN ACTIVIST TO TRUMP: ‘MAKE CUBA GREAT AGAIN’ BY ENDING COMMUNIST RULE

President Trump in Oval Office

Gray’s remarks come amid a total power grid failure that plunged the Caribbean island into darkness. 

Fox News senior White House correspondent Peter Doocy questioned the president about the country on Monday, asking, “When you say Cuba is next, is Cuba – whatever you do with the military there, it seems like something – will that look more like Iran or Venezuela?”

Trump replied, “I can’t tell you that. I can tell you that they’re talking to us. It’s a failed nation. They have no money, they have no oil, they have no nothing.”

“I do believe I’ll be… having the honor of taking Cuba… That’s a big honor,” he added later.

Various geopolitical developments under the Trump administration have fueled speculation that Cuba’s communist regime could soon be next in the president’s playbook, including Venezuelan dictator Nicolás Maduro’s removal from power and even more recent strikes against the Iranian regime.

Fox News’ Greg Norman-Diamond contributed to this report.

Read the full article here

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