Is Cuba Ready to Fall?

President Donald Trump delivers remarks at a press conference at Mar-a-Lago in Palm Beach, Florida, following Operation Absolute Resolve in Venezuela, leading to the capture of Venezuelan President Nicolas Maduro, Saturday, January 3, 2026. (Official White House Photo by Molly Riley)

UPDATE 1.13.26: President Trump has put Cuba on notice that there will be no more money or oil coming to it from Venezuela.


To Avoid Capture, Go Somewhere Unknown

“If you are really trying to avoid capture, you go to places people don’t know about,” a former US military officer told the WSJ.

Escape: 101

“You wonder why Maduro didn’t go to some nondescript apartment in the middle of Caracas or the countryside.”

Intelligence is critical in protecting VIPs. Patterns of life, daily habits, and routine can seem mundane, but become critically important in helping to keep VIPs safe. For example, it is well known that Russian President Vladimir Putin goes to great lengths to maintain secrecy about his movements, residence details, or workspaces.

Become Unknown

Is there trouble for Havana’s leaders? Maduro’s capture was bad enough. There was more carnage. Cuba reported that 32 officers assigned to a safety detail for Venezuela’s strongman were killed. This doesn’t augur well for Cuba’s leaders.

Cuban intelligence, known for decades as Cold War stars, just had its invulnerability punctured.

U.S. elite forces descended on Maduro’s compound at around 2 a.m. local time Saturday, grabbing him and his wife before they could escape to a safe room, said Gen. Dan Caine, the chairman of the Joint Chiefs of Staff.

Cuba’s defeat indicates its weakness, according to María Werlau, author of “Cuba’s Intervention in Venezuela,” a book published in 2019.

Relied upon by the Soviet KGB for its extensive informant networks in Latin America and Africa, Cuban expertise to protect allies, detect unrest and suppress dissent became a lucrative export. After the collapse of the Soviet Union, Cuba’s security and intelligence services secured a lifeline from oil-rich Venezuela as Havana inched closer to economic collapse.

Old School Craft

Despite a U.S. armada threatening the Venezuelan leader for months from the Caribbean, how did Cuba’s security detail fail to defend Maduro? Perhaps even worse, Cuba’s security failed to inflict any damage on the Americans, points out  Jorge Castañeda, Mexico’s former foreign minister and author of several books about Cuba’s regime. “This means the Cubans weren’t where they needed to be, with the strength they needed to have.”

These intelligence flaws are likely to hurt the communist regime at home, writes the WSJ, especially should Cuba lose its economic support and subsidized oil shipments amid an unprecedented economic implosion.

“The people can go hungry, but the repressive apparatus must have privileges,” offers Enrique Garcia, a former Cuban intelligence officer who defected to the U.S. “If the regime loses all economic capacity, no system can withstand it.”

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Debbie Young
Debbie, our chief political writer at Richardcyoung.com, is also our chief domestic affairs writer, a contributing writer on Eastern Europe and Paris and Burgundy, France. She has been associate editor of Dick Young’s investment strategy reports for over five decades. Debbie lives in Key West, Florida, and Newport, Rhode Island, and travels extensively in Paris and Burgundy, France, cooking on her AGA Cooker, and practicing yoga. Debbie has completed the 200-hour Krama Yoga teacher training program taught by Master Instructor Ruslan Kleytman. Debbie is a strong supporting member of the NRA.