Trump has said that he can “take Cuba anytime.” But if he expects a walkover like Venezuela, he should think again. While Cuba’s proximity to the U.S. and collapsed economy should make it an easier target, its totalitarian system better resembles that of Iran, whose resistance to U.S. military and economic pressures may be inspiring Cuba’s besieged communists to do the same and possibly coordinate their moves with the IRGC.
Cuba and Iran have maintained close relations since the earliest days of the Islamic revolution, when the Castro regime was among the first governments to officially recognize the radical Islamic mullahs who took power in 1979 with organized violence and summary executions, much as Fidel Castro did in 1959.
According to Western intelligence reports, Cuba’s spy agency (DGI) assisted the forerunners of the Islamic Revolutionary Guard who invaded the American embassy in Tehran, helping with the analysis of seized U.S. intelligence documents. On a 2001 state visit to Iran, Castro declared at the University of Tehran that “Cuba and Iran working together will bring the American empire to its knees.” (RELATED: Darkness Before the Light in Cuba)
U.S. security officials suddenly reveal that Cuba has 300 Iranian kamikaze drones targeting southern Florida.
Successive Iranian presidents and IRGC generals have visited Cuba and its Latin American allies in Venezuela, Nicaragua, Bolivia, and Brazil, where Quds Force and Hezbollah have set up extensive support networks. Past U.S. administrations have downplayed Cuba’s Iranian connections. But as tensions with Havana have escalated since Trump’s Venezuelan intervention and his imposition of an oil blockade on Cuba, U.S. security officials suddenly reveal that Cuba has 300 Iranian kamikaze drones targeting southern Florida. (RELATED: Cuba on the Cusp: Getting the Story Right This Time)
Recently defected Cuban military officers consider the number a joke, telling The American Spectator that hundreds more Iranian Shaheds, older Mohajer-6s, as well as upgraded Russian models could be assembled at secret facilities in Cuba. Iranian drone factories have operated in Venezuela and Bolivia, according to U.S. intelligence sources. Cuban drone pilots have trained and operated with Russian UAV battalions in Ukraine, where 20,000 Cuban “mercenaries” have been serving with the Russian army, according to Ukrainian intelligence reports.
Despite Cuba’s crippling fuel shortages, rolling blackouts, economic paralysis, and growing food shortages, the communist regime expects that it can wait out the U.S. blockade and counter a U.S. military intervention, according to sources inside Cuba. It has plans for a “people’s war” merging the regular army of about 50,000 with politically controlled militias currently organized for internal repression as Committees for the Defense of the Revolution (CDR).
“They have been preparing for a U.S. invasion for decades,” says Carlos Calvo, a Cuban army lieutenant who served with the elite Punto Cero unit, the Praetorian Guard of the Castro family, and other high-level regime officials. He says that Cuba’s asymmetrical warfare strategy is based on tactics developed by communist forces during the Vietnam War, imparted by North Vietnamese instructors who have trained guerrilla groups from all over Latin America, including Colombia’s FARC and ELN.
The recently issued U.S. murder indictment against Fidel Castro’s brother, Raúl, who succeeded Fidel as president upon his death and still presides over the armed forces as he has done since the start of the “Revolution,” indicates U.S. plans for a Maduro-style regime decapitation with the hope that a more moderate and acceptable figure fills his vacancy. (RELATED: The Man Behind the Dictator)
But Raúl Castro’s security is tighter and far more extensive than was Nicolás Maduro’s in Venezuela, according to Calvo. Punto Cero’s 800 highly trained and indoctrinated bodyguards protect him at all times, moving wherever he goes and guarding his various fortified residences and command bunkers. They are selected from Cuba’s special forces known as Avispas Negras (Black Wasps), armed to the teeth with Russian AKM automatic rifles, RPG-7 anti-tank rockets, Igla shoulder-fired SAMs, and BTR armored personnel carriers.
Calvo recalls being a subordinate to Punto Cero’s chief Colonel Alfonso Roca, who headed Maduro’s Cuban security team in Venezuela and died in the savage firefight with Delta Force along with 30 of his men on the night that U.S. Special Forces descended on the presidential compound in Caracas. While surprised and overwhelmed by Delta’s dead-accurate firepower and SOAR attack helicopters, the Cubans managed to hit a Chinook, seriously wounding its pilot and a half dozen Delta commandos.
Castro’s main fortified residence in Havana is surrounded by a jungle of trees and minefields, which make a special forces helicopter landing “impossible to execute,” says Calvo. Castro can also take refuge in a network of underground command bunkers connected by tunnels, where large numbers of soldiers can be housed and big quantities of weapons, ammunition, and other supplies stored.
Chinese and Russian electronic spy stations in Cuba can intercept U.S. military communications with powerful antennas designed to resist jamming and provide early warning of a U.S. sneak attack.
“We cannot repeat the same operation we did in Venezuela,” says U.S. Army War College professor and Latin America specialist, Dr. Evan Ellis. He expects initial U.S. air strikes on Cuba to be directed at one or two of the main “command nodes” to possibly take out Castro with a drone, missile, or bunker-busting bomb similar to how Iranian Supreme Leader, Ali Khamenei, was eliminated in the first bombing strike of Operation Epic Fury.
Castro is charged with the murder of four Americans in two aircraft shot down by Cuban MiG fighters on his personal orders in 1996. However much delayed the response has been by the U.S. establishment’s reticence to confront Cuba, the incident warrants the kind of targeted assassination regularly carried out against terrorists who kill Americans. U.S. investigations further indicate that the air attack on the unarmed Cessna planes of Brothers to the Rescue was carefully planned in advance, involving an elaborate DGI operation in Miami to penetrate the exile group.
But Raúl Castro’s elimination is unlikely to produce a Cuban Delcy. Puppet president Miguel Díaz-Canel is a communist party apparatchik and a trusted appointee of the Castro family, whose other members would remain in control of the security services. Raúl’s son, Alejandro, is a senior colonel in the DGI, where a nephew is a lieutenant colonel. His grandson, called “The Crab,” who wears gold medallions and follows Raúl everywhere, is a chief thug in Punto Cero.
A former U.S. intelligence officer who has operated in Cuba says that it might be possible to leverage sectors of the regular army to dislodge the Castros. But most Cuban senior generals are partners with the Castros in GAESA, the conglomerate of state-owned enterprises whose accumulated profits from tourism, mining, and other ventures are distributed privately, similar to how the IRGC manages Iran’s economy.
Retired U.S. Special Forces colonel Ron MacCammon, who served as U.S. military attaché in Venezuela, says that Cuba may threaten to flood the U.S. with a refugee exodus larger than that unleashed by Fidel Castro in the 1979 Mariel boatlift, to pressure Trump. “They will time it to influence the midterm elections, in which a victory by leftist democrats would play into their hands.”
Last week, the Trump administration moved to shut down a U.S. network of radical left activist groups with known ties to Cuba, which have been involved in violent pro-Hamas anti-ICE and other organized protests. One of the militant leaders, Manolo De Los Santos of the New York–based Peoples Forum, recently toured Havana with a DGI agent involved in the Brothers to the Rescue shootdown, who is now a chief officer of the CDRs, as reported in Cuba’s official newspaper, Granma.
Secretary of State Marco Rubio was less than sanguine about prospects for a negotiated transition in Cuba in recent Senate testimony. He cited conversations with regime “technocrats who agree that the situation in Cuba is unsustainable.” But the Castros control the guns as well as a vast intelligence and terrorist network stretching throughout the western hemisphere, enabling Cuba to strike America’s weak points. (RELATED: The Son of Cuba Takes on the Last Communist Neighbor)
Military action against Cuba may be inevitable. Dr. Ellis expects operations to start within weeks. Airborne troops and Marines are being prepositioned at SOUTHCOM bases in southern Florida, Puerto Rico, and the Cuban base of Guantanamo. The USS Nimitz aircraft carrier strike group has moved into the northern Caribbean to cover Cuba’s southern coasts as surveillance flights multiply around the island. But a realistic ground strategy, requiring the organization of an armed insurgent movement in Cuba, needs to be in place. And if it can’t be done in Cuba, what hope is there in Iran?
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