If President Donald Trump’s recent comments are to be believed, he wants regime change in Cuba. Even after seizing a wanted dictator out of Venezuela and while monitoring an air war in Iran. Along with ongoing military tension with Mexican drug cartels. Against that backdrop of cross-global conflict, the decadeslong tension between the island nation and the U.S., just 90 miles from the Florida Keys, looks ready for its final act.
“Cuba is going to fall pretty soon,” Trump told CNN. “They want to make a deal so badly … I’m going to put [Secretary of State Marco Rubio] over there, and we’ll see how that works out. We’re really focused on this one right now. We’ve got plenty of time, but Cuba’s ready after 50 years.”
Already struggling with economic sanctions imposed by Trump, the communist stronghold sees current leader Miguel Diaz-Canel — the regime’s successor to the late Fidel Castro and his 94-year-old brother Raúl — holding a tenuous sway over a weakened country less likely to garner support from a Ukraine-obsessed Russia, or from China with its Iranian allies under daily attack. If U.S. forces were to attempt a takeover akin to the special forces action in Caracas, Cuba might have to face the threat on its own.
Ravi Balgobin Maharaj is a Caribbean affairs analyst based in Trinidad and Tobago. He considers outdated notions that the current tension between the U.S. and Cuba is merely a lingering hangover from 1961’s Bay of Pigs invasion, 1962’s Missile Crisis, or the 1999-2000 Elian Gonzalez controversy. Instead, he sees an altered version of the 1823 U.S.-issued Monroe Doctrine, which declared the portions of the Western Hemisphere under American influence off-limits to European (and eventually Russian or Chinese) influence.
“We are witnessing the final chapters of a very old story,” Maharaj said. “While many believe those 20th-century scars provide the emotional fuel for policy, the 21st-century engine is driven by (Donald Trump’s) cold, calculated ‘Donroe Doctrine.’ This isn’t just about communism anymore. It’s about the aggressive removal of Chinese and Russian intervention in our hemisphere and the total consolidation of regional natural resources.”
Some wonder if American resources are spread too thin for action in Cuba in light of the joint Israeli-U.S. action over Tehran. Maharaj, though, expects that any potential action in Cuba was accounted for by the State Department and the War Department before the Iran operations began.
“In this administration’s view, the board is interconnected,” he explained. “The collapse of the Maduro regime in Venezuela on Jan. 3 wasn’t an isolated event. It was the removal of Cuba’s primary energy artery. Far from being distracted by Tehran, Washington is using the momentum of the Iran conflict to settle backyard accounts.”
Maharaj insists the Trump administration sees the Tehran-Moscow-Havana axis as a single entity, warranting moves to ensure that, while the U.S. military is engaged abroad, no rival power can use a desperate Cuba as a strategic or electronic foothold near American shores.
“The strategy isn’t simply to sit back and watch Cuba self-destruct in the dark, either,” Maharaj said. “We are seeing a much more surgical approach to ‘regime dismantling’ through the control of energy.”
Clark H. Summers, Ph.D., is Assistant Professor of Government and Political Philosophy at Belmont Abbey College in North Carolina. He makes it clear that Cuba poses no current threat to the U.S. itself, but it could be useful to America’s more distant enemies like Russia and China, who worry about losing Iran as a major ally.
“Cuba is less a strategic problem for U.S. interests in the Caribbean and the Western Hemisphere, but more of a means by which more significant ‘bad actors’ are able to exert influence or project power,” Summers said. “North Korean and Russian interests would be negatively impacted by a regime change in Havana.”
As for China, Summers believes its efforts to grow and strengthen regional influence would diminish. Meanwhile, he sees some immediate U.S. domestic economic boost should there be military action against Cuba.
“It is likely that there would be an initial surge of remittance and relief money from the Cuban-American community, as well as a potential flood of American tourists seeking to visit,” he said. “Tourism and developing business markets may stimulate the first real economic development among the general Cuban populace in more than 60 years.”
However, Summers warns that there is no reason to expect the Cuban population to possess the cultural norms and attitudes to make a smooth transition to a more open, free-market economy.
“Much of the necessary social infrastructure — legal systems, rule-of-law, and trust in local law enforcement — will take time to develop, perhaps one or two generations,” Summers said. “Unless the U.S. is prepared to invest significant resources with ‘boots on the ground,’ a sudden collapse or removal of the current Cuban government will likely result in significant pain and disruption to the average Cuban.”
Michael Montgomery is a political scientist and former U.S. diplomat who once coordinated State Department involvement in the American embargo of Cuba. He is now a Human Services professor at the University of Michigan-Dearborn. Montgomery agrees that the Cuban people are currently suffering and would continue to struggle with or without U.S. intervention. In fact, he sees the island nation eventually heading toward total collapse.
“Without access to Venezuelan oil, the lights in Havana will just flicker out at some point, leading to some kind of regime change without the expenditure of U.S. blood,” Montgomery said. “There is no high-profile ‘bad guy’ analogous to [former Venezuelan President Nicolas Maduro) in the current Cuban government who might be captured in a comparatively low-risk extraction mission.”
Montgomery points out that the Cuban military is larger than Venezuela’s and backed up by reserves. Any kind of conventional intervention would likely prove more costly than the Maduro operation.
“Cuba is boxed in economically,” he said. “Although other nations have never supported our longstanding embargo on Cuba, the Cuban government doesn’t access to enough hard currency at this point to buy what it needs, and there’s not sufficient oil from non-Venezuelan sources.”
Regarding Cuba’s long-standing and currently expanding economic pitfalls, Williams College political science professor James Mahon Jr. says the seeds for the downfall were sown decades ago.
“The great puzzle of Cuban economic reform has always been why they did not take the Vietnam/China route to ‘market socialism,’” Mahon said. “It appears that the Castros did not trust Cubans to get rich. They might’ve been afraid that rich Cubans would become a fifth column for U.S. manipulation and influence. To be fair, the country’s history may have taught [the Castros] this, but the policy has been disastrous.”
Mahon wonders if Rubio — a longtime, earnest critic of the island’s government whose parents fled from Cuba — is so determined to be its liberator that he will not accept anything less than military action.
“The obvious risk of this current [U.S. sanctions] policy is that it will create economic desperation worse than what gave us the Balseros,” referring to the raft-riding Cuban refugees of the 1990s. “Cuba knows how to weaponize the emigration of desperate people. Once they start arriving, where will they be deported? The optics will be poor.”
Professor Summers focuses on the strategic challenges of invading Cuba and believes they alone provide enough reason for the U.S. to keep its powder dry for now.
“I think military action against Cuba is very unlikely,” Summers concluded. “Although U.S. SOUTHCOM performed well in Operation Absolute Resolve, the resources necessary to repeat such an action — logistical, personnel, training, and operational — will demand a lot of time and money.”
Considering possible hard-line U.S. military action in or over Cuba, Summers reminds those monitoring Cuba that American resources still maintain a functional blockade of Venezuela and could need to manage rescue operations into cartel-afflicted Mexico. Both conditions make an ad hoc aerial campaign without clear attainable objectives less likely.
“There’s no significant land force at hand to conduct the necessary security mission, and the Trump administration has shown no predisposition to commit U.S. troops to such activity,” he said.
Looking ahead and monitoring the Iranian conflict, Maharaj anticipates that the trajectory after the Iranian situation stabilizes will become clear quickly.
“The U.S. is positioning itself for what I call a managed transition,” he said. “By controlling the flow of oil into the island via new private-sector licenses, Washington is already picking the winners and losers of a post-Castro Cuba.”
Maharaj urges observers to expect more maritime friction as the U.S. Navy increases safety patrols to protect private fuel shipments, eventually leading to a scenario where the Cuban government is forced to concede its sovereignty over the economy or face an internal uprising fueled by the very energy the U.S. is now providing.
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With all this in mind, Montgomery sees no reason for Trump to step down hard on Cuba.
“The smart play here would be to talk tough, but basically just wait for Cuba to collapse in on itself,” he said. “When that happens, declare victory.”
John Scott Lewinski (@johnlewinski) is a writer based in Milwaukee.















