AFTER THE END
How Cuba might change and what it will look like after is the big question.
News reports emerged today that CIA Director John Ratcliffe was in Havana yesterday to meet with senior figures in the communist regime of Cuba to discuss a reported $100 million aid offer along with easing of economic sanctions in exchange for “fundamental changes” to the dictatorship’s political system. The visit came amidst 22-hour blackouts across Cuba as fuel reserves have fully run out and protests broke out Wednesday night in neighborhoods within the capital.
Today it was also reported that the U.S. Department of Justice will seek to indict former President Raúl Castro in connection to the 1996 downing of humanitarian planes. Castro’s grandson, Raulito, was among the regime figures that Ratcliffe met this week. After years of refusing any negotiation on political changes, President Miguel Diaz-Canel today said he was willing to consider the U.S. aid offer without mentioning — or outright refusing — a wider political negotiation.
What is underneath?
The consensus among many observers this week is that the communist regime in Cuba is approaching its end. The successful removal of Nicolas Maduro from Venezuela by U.S. special forces in January, followed by the termination of Venezuelan oil supplies to Cuba, has accelerated a process that has been long coming, they argue.
There has been a long-standing political community of Cuban-Americans in South Florida, united in their determination to bring down the communist regime despite it often seeming out of reach for over 60 years. They have become a powerful faction in the Republican Party throughout its various shifts in leadership and ideological direction, railing against any softness or accommodation with the regime. With Secretary of State Marco Rubio, himself a Cuban-American, playing a central role in the Trump Administration’s Cuba strategy, they may be closer than ever to realizing that dream even if the outcome lacks the cinematic drama of the overthrow of the Eastern European communist regimes in 1989.
And like the Soviet and satellite states as they reached their end, everyone but the robotic propaganda mills can see that Cuba’s economic and political model failed on its own many years ago. Even Fidel Castro, in a late-day moment of candor in 2010 to The Atlantic’s Jeffrey Goldberg, admitted “the Cuban model doesn’t even work for us anymore” when asked if he still saw reason to export it.
When its Soviet sponsors disappeared in 1991, Cuba fell into a deep crisis along with its fellow travelers in North Korea. The so-called “Special Period” that followed has been emblematic of the inherent lie at the heart of the Cuban model. The name suggested a temporary glitch in the socialist matrix when, in fact, it was permanent and impossible to reverse. This was despite billions of dollars in global tourism revenues, hundreds of millions in Spanish and Canadian joint venture investments and unusually favorable trade conditions from China, Russia and Venezuela designed to lift up the regime’s own vision of socialist development.
When Maduro was captured, Russia and China essentially shrugged. Now that Cuba’s regime is failing, they have again done nothing meaningful to intervene diplomatically. President Donald Trump was in Beijing while Ratcliffe was in Havana, and there are no indications that Cuba ever came up between Trump and Chinese leader Xi Jinping. So much for the decades of slogans and “fraternal” actions in Cuba’s favor. They were nothing but geopolitical games aimed at the United States, now past their sell-by date.
The anticipated indictment of Raúl Castro will add vivid leverage to the discussions that Ratcliffe helped advance this week. It may not be the last indictment of a regime figure, and would put targets on all of them for special forces actions like the one that rendered Maduro to Rikers Island and left dozens of his Cuban security forces dead. Like Delcy Rodriguez faced in Caracas in January, they are all being told in one way or another to cooperate with U.S. negotiators on a transition strategy or tempt Maduro’s fate.
So how might a transition begin - if it does? Would it require some kind of military action by the U.S. or a popular uprising to tip the scale? Before Maduro’s capture and its aftermath, conventional wisdom would have said, yes, that the Cuban regime would never give an inch in order to safeguard its sovereignty and would have to be attacked from without or within. But things feel different now to many observers.
First off, the Cuban people blame those in power for their suffering now, not the United States. They are increasingly angry and discontented over shortages, misery and the collapse of the power grid. There is a palpable sense that the incumbent government has lost any credibility and has basically given up, so Diaz-Canel and whoever else he puts on TV to defend the government can’t count on the people’s loyalty.
Second, the regime has become less of a revolutionary communist dictatorship and more like the Batista government it overthrew in 1959. As part of the “Special Period”, Raúl Castro created the Grupo de Administración Empresarial S.A. (GAESA) in the 1990s as an arm of the Cuban military that came to own and control nearly every aspect of the country’s economy. It operates as a very disciplined mafia straddling the state-owned and “privatized” areas of all sectors, hoarding and siphoning off profits and capital while also controlling key banking and commercial trade channels in and out of the country. It has fortified its relatively small elite while creating a level of economic inequality for the Cuban people that is objectively worse now than the pre-revolutionary period.
Third, while the current leadership is as deeply unpopular in Cuba as Maduro’s regime was in Venezuela, the state security apparatus in Cuba is as strong as it’s ever been. The Venezuelan regime was always more from the authoritarian mold, with power divided among rival factions and a ham-fisted approach to repression. Cuba has always been a totalitarian dictatorship with a highly developed system of surveillance and control, and a tightly unified governing structure. That means two things at the same time: the regime can usually deactivate most public uprisings before they pose a threat, and it can largely hold together internally against efforts to divide and conquer it.
If the crisis drags on and the Cuban people don’t play along with state propaganda in blaming the U.S. for the increasingly visible suffering they will experience, the situation could become uncomfortably messy for the regime. This had probably been dawning on the leadership ahead of Ratcliffe’s visit this week, and we have yet to see whether the talks might end up shaking something loose from the standoff.
Our take:
What appears to be taking shape as Washington’s strategic gambit is to probe whether Cuba could be an easier, “cleaner” version of the Venezuelan outcome. Hold out the possibility of varying degrees of “decapitation” as conditions worsen on the ground in order to push the military elite to see an opportunity taking shape rather than a threat.
Unlike in Venezuela, where the regime was a tin-pot gaggle of gangsters pitted against each other, Cuban’s military is an intractable octopus poured into and coiled tightly around everything of value on the island. That also makes it somewhat invisible as an entity. Like an octopus, any part of a limb that gets severed would regenerate and it can change its colors and texture to pretend it is something else in order to survive.
Diaz-Canel and any other political face of the regime could be easily tossed aside and the military would be largely untouched. That might be looking like a good idea about now, and it is probably what the Trump Administration is trying to precipitate.
The top military brass and their effective minions at GAESA, as they look out at their blacked-out and restive island, need only to remember what happened in Venezuela and see how easy it could be for them. They could toss out much of the incumbent government and make a deal with the Americans that both sides will agree constitutes “fundamental changes”. The U.S. may get favorable economic terms in exchange for easing sanctions along with other concessions that will look like the communist model has been junked and China has been sidelined. In the end, Washington would get the major political win it seeks and the Cuban military - probably with a change in color and texture - will remain in power.
It would certainly be better for both sides than any military confrontation, large or small. The Cuban military has been preparing to repel a U.S. invasion for more than half a century and even in its weakened posture today, most are confident that Cuba will put up a bigger fight than Venezuela. And don’t believe the regime’s own protestations that it has “run out” of all forms of fuel. That pertains only to the people; the military has certainly stockpiled enough resources for its own defensive strategies. It would probably be a bloody affair with costs to both sides that neither will want to shoulder, particularly in light of the Iran conflict’s political impact in the United States.
And Iran is also a lesson to both sides of the Cuba question. Iran’s regime didn’t crumble like some in Washington thought it would, given its willingness to murder tens of thousands of its own people without losing its trading partners around the world. The Cuban regime will not tip over with just a gentle shove even now. Iran’s military has also woven itself deeply into the country’s economy and governing apparatus. When the religious leadership was killed off in the opening hours of the war, the military simply supplanted them and took full control.
But Iran has oil and has tactical control of the Strait of Hormuz. Cuba has nothing like these advantages in its toolkit. All the more reason to consider the upside of making a deal that allows the regime to recombine, live on and maybe even prosper. They could get the beneficial treatment that Delcy Rodriguez received without any fear of internal strife, the consolidation of power the Iranian military pulled off, and all without a single bomb or American soldier landing on their territory.
It’s all still very theoretical, of course. The Cubans have the chance to show they are not as addled by ideology and hubris as their revolutionary founder often was. They might choose to see themselves as lucky, or the beneficiaries of some kind of providence, that they came third after Venezuela and Iran. Time will tell.

