What Was the Cuban Revolution? The Dream Is Dying but the Myth Will Persist
Just how and when the Cuban dictatorship will disappear is impossible to predict: a deal with Donald Trump to build hotels in Varader; the Marines welcomed by crowds on the Havana Malecón; popular protests overwhelming an army unwilling to fire on its people; a real, necessary and desirable peaceful transition to democratic rule and economic reform. Dozens of experts and pundits have lost their shirts betting on the regime's demise since 1959. The convergence of new factors, however, suggests that Cuba has entered a new and probably terminal phase. Its economic collapse, the end of the Venezuelan subsidy, the Trump administration's willingness and ability to squeeze it further, the growing discontent and protests of the island's inhabitants, are all factors that were absent in prior decades.
But those unknowns only mask a certainty: The idea of the Cuban Revolution and the historical forces it unleashed have already been extinguished. For nearly half a century, a persistent external attraction and fascination allowed Cuba and its outsized leader to punch way above their weight in international affairs. Partly out of a cunning strategy for dealing with the United States, partly out of sheer megalomania, Fidel Castro was able to project his revolution's impact well beyond the island's shores: in Latin America, in Africa and in a different, more defensive fashion, in the United States and Europe. Not to mention the Soviet Union, which made Cuba a centerpiece of its foreign policy for 30 years. Perhaps the only other nation of a similar population (on par with Paris) and with similar clout on the world stage has been Israel, with a similarly powerful military and intelligence service.
The proximate cause of the end of that revolutionary allure was the fall of Venezuelan President Nicolás Maduro-and the intimate role Cuba played. When American operatives extracted Maduro in January 2026, they did so by first eliminating the Cuban security detail that formed his innermost ring of protection. With Maduro gone, President Trump announced that he would "run" Venezuela. But, in the hours after the operation, Secretary of State Marco Rubio-for whom the end of the Castro regime has been something close to a lifelong personal mission-made it clear that Havana was the ultimate target: "It was Cubans that guarded Maduro."
While much of the newly compliant Venezuelan regime was kept in place, the lifeline that had kept the Cuban regime alive for a quarter century-between $4 billion and $6 billion annually in subsidized oil, hard currency and preferential trade-had been severed. Cuba's electrical grid, already in cascading failure since 2024, lost what little fuel remained. After the Venezuela raid, power cuts across more than half the island lasted upward of 20 hours a day; the country ran out of diesel entirely; the U.N. declared a humanitarian emergency.
Washington moved quickly to ensure there would be no rescue. In February, the United States imposed what amounted to the first effective naval blockade of Cuba since the Missile Crisis of 1962, intercepting oil tankers and threatening supplier countries with tariffs until all complied. Rubio sanctioned Grupo de Administración Empresarial S.A., the military conglomerate controlling between 40 and 70 percent of Cuba's economy. Cuba's external patrons-the Soviet Union, Venezuela-had been, exhausted or defeated. Russia remained too consumed by its own predicament with Ukraine to compensate, and China's heart was never in it despite donations of solar panels without batteries to alleviate the power collapse.
Trump, at a Miami summit in late March, confirmed the logic in sequence: "Cuba is next." The clearest signal came in May, when CIA Director John Ratcliffe flew to Havana and met with Raúl Guillermo Rodríguez Castro-Raúl Castro's grandson, known as Raulito or El Cangrejo (the crab), who oversees the family's interest in GAESA-delivering Trump's terms while the CIA posted photographs of the encounter on social media. Then, on May 20, the Justice Department indicted Raúl Castro for murder for ordering the downing of two planes with Americans in 1986. "We have Cuba on our mind," Trump said shortly afterward.
***
Now that the Cuban revolution's attractiveness has faded and its final days seem closer than ever, a look back on a fascinating, though largely futile, story is instructive. From the outset, Castro believed that by supporting revolution throughout Latin America, he could both distract Washington from adventures like the Bay of Pigs and Operation Mongoose and, at the same time, put an end to Havana's isolation. From early on, the Kennedy Administration was able to force nearly every nation in the hemisphere-Mexico and Canada were exceptions-to break off trade, travel and diplomatic relations with the island. Castro's response was to sponsor armed struggles through guerrilla groups nearly everywhere in Latin America, again, with the exception of Mexico.
Régis Debray, a young French intellectual, provided the theoretical underpinning for the armed route to revolution in Latin America in a book prefaced by Fidel himself: Revolution in the Revolution? Castro trained young potential combatants from Venezuela, Colombia, Guatemala, Nicaragua, Argentina, the Dominican Republic, Peru and later Bolivia and Brazil in camps near Havana, mainly in one named Punto Cero. Manuel Piñeiro, his "Minister of Revolution" and known as Redbeard, armed and indoctrinated them then dispatched them off to the jungles and mountains of their respective countries.
Excepting the Sandinista Front in Nicaragua, which fought its way to power in 1979, all of these attempts failed, and hundreds, perhaps thousands of young Latin Americans died in a misguided fight based on a misguided reading of the Cuban Revolution itself, by misguided leaders, as heroic as they may have been. Father Camilo Torres' remains were just recently found and consecrated in Colombia, more than 50 years after his death; those purportedly of Che Guevara were buried in a memorial in Santa Clara, Cuba-where he won his greatest battle in 1958-on the 30th anniversary of his death in 1997. The Argentine armed group led by Ricardo Massetti collapsed in 1964. And so it went.
But the failure of all of these guerrillas-in Brazil, led by Carlos Marighella, in Venezuela by Douglas Bravo and the Petkoff brothers, in Peru by Luis de la Puente, by Raúl Sendic and his Tupamaros in Uruguay-did not only cause the deaths of their participants. Their existence and, occasionally, their threat to the status quo, legitimized the brutal repression carried out by the armed forces of many of these countries. The multiple military coups of the '60s and '70s were not all a response to armed struggles, but they justified the death, disappearances and torture of thousands of students and workers in many, if not all, of the nations of Latin America. Again, only Mexico was spared military rule.
***
Central America and Angola in the '70s and '80s were a different story. In Nicaragua and El Salvador, and to a lesser extent in Guatemala, the Cubans armed and assisted well-implanted, long-standing mass movements that also had an armed component. They were able to send large amounts of weapons to Nicaragua and El Salvador, experience Chilean advisers to Nicaragua and coordinate their aid with excellent, real-time communications with Havana from all three countries. The Sandinistas overthrew the Somoza dictatorship and remained in power for 10 years. Their political survival was partly insured by the help of thousands of Cuban security personnel backing their response to the so-called Contras, trained and armed in neighboring Honduras by the Reagan Administration. When Daniel Ortega returned to office through elections in 2007, he gradually established a new dictatorship, in power still today.
In El Salvador, the FMLN guerrillas fought the U.S.-backed military to a standstill in 1989 and eventually signed a peace agreement in 1992 that allowed them to win the presidency on two occasions. The Cuban connection was key in their fight and their years in government, although they concluded in disgrace, with the 2019 election of strongman Nayib Bukele, who may well be around for several decades.
The Angolan and Ethiopian expeditions in the '80s ended poorly in the latter case, and successfully in the former one. Thanks to Operation Carlota in Angola in 1975, Cuba funneled thousands of well-trained troops, largely of Afro-Cuban descendance, to the former Portuguese colony in support of the MPLA, competing for power with the American-backed UNITA led by Jonas Savimbi and the Chinese-supported FNLA. At the 1988 Battle of Cuito Cuanavale, the Cuban contingent, said to have been personally commanded by Fidel Castro from Havana, defeated the South African army and consummated Angola's independence under a Cuban-backed regime.
But the expedition to the Ogaden region in support of Ethiopian leader Mengistu Haile Mariam in the late '70s ended less favorably. He was removed from power in 1991 and later convicted of human rights violations under the Ethiopian Red Terror. President Reagan's Secretary of State Alexander Haig once complained to Cuban leader Carlos Rafael Rodríguez that Washington had intercepts of Cuban pilots in Russian MiGs exchanging flight instructions in Spanish over the Ogaden. This was one more extreme example of Cuban international projection, thousands of miles from the Caribbean.
***
By the mid-'90s, with the collapse of the Soviet Union and the cancellation of its massive subsidy to Cuba's economy, most of these adventures came to an end. Castro lacked the resources and the opportunity to pursue them. But a new foreign venture soon appeared, in the figure of Hugo Chávez in Venezuela, elected president in 1999. Fidel achieved one of the most impressive feats in modern international relations: A poor, small, sparsely populated island practically colonized an oil- and resource-rich nation with more than three times its population. For a quarter century, Chávez and his successor Maduro provided cheap or free oil as well as hard currency to Cuba in exchange for thousands of doctors, sports instructors and intelligence and security agents. Cubazuela was born and thrived during this period.
Castro was once again able to project his ideas of Latin American sovereignty, anti-Americanism and social welfare in exchange for the elimination of democratic institutions and individual freedoms. Chávez became his partner and enabler, providing subsidized oil to many nations in the region, lobbying against the idea of a Free Trade Area of the Americas Agreement and in favor of the first "pink tide" in Latin America. With Castro masterminding the operation, left-of-center regimes from Bolivia to El Salvador, among the island-states in the Caribbean and elsewhere benefited from Chávez's largesse until his illness sidelined him in 2011. Thanks to the Venezuelan oil bonanza and a long-standing presence in Africa through medical teams, Cuba was able to secure broad diplomatic support in the United Nations General Assembly and other U.N. agencies, though its record in Geneva's human rights bodies was far more contested.
The Cuban Revolution's influence beyond its shores, however, was not limited to these characteristics. In many Latin American, African and European countries, sympathizers and outdated admirers of the regime formed groups, institutes, centers and multiple associations of "friendship" with the island. These also included left-wing political parties closely linked to the Department of the Americas, Minister of Revolution Piñeiro's outfit in charge of relations with nongovernmental actors abroad. Often named for independence hero José Martí, frequently invoking the notion of "solidarity" with Cuba, these nuclei of supporters were extraordinarily useful to Castro and his regime.
Most of the time they concentrated their energies and activities on cultural events, the commemoration of iconic dates, welcoming Cuban dignitaries and, in general, promoting the island's feats and interests. But whenever a local government crossed the dictatorship with a vote at the U.N. or abiding by American sanctions or restricting travel or trade with Cuba, these groups would transform themselves into a type of fifth column. They would organize demonstrations against the authorities, publish articles and comments in the press critical of the government and hold forth in universities, cultural institutions and the media in Castro's defense and in opposition to local policies.
In many ways, though without the resources, they replicated the Soviet model during the Cold War: civil society groups sympathetic to Moscow, alongside powerful Communist Parties in some countries-Italy, France, Chile, Uruguay-and myriad writers, poets, artists, dancers and filmmakers, always ready to defend the "party line" as determined by the Soviet regime.
The first and second "pink tides" in Latin America, in the early years of this century and subsequently during the current decade, together with Venezuelan funding, allowed the Castros to live on borrowed time and maintain their halo abroad, well after their revolution had run out of resources and prestige. Cuba became a founding member of the Community of Latin American and Caribbean States (CELAC), its dream of an Organization of American States without the United States or Canada.
It continued to send thousands of doctors to Africa and Latin America, so much so that the sums paid to the Cuban government by foreign nations became the regime's principal source of hard currency. The medical teams brought goodwill and local networks in addition to badly needed dollars and, over time, represented one of Cuba's best international calling cards. It was not until the second Trump Administration that the U.S. "persuaded" countries like Jamaica, Honduras, Guatemala and Guyana to cancel these missions, but many others, from Mexico to Calabria in southern Italy, retained them.
***
This detailed description begs a question. How did a tiny island, a failed experiment and a regime only able to survive thanks to recurrent, massive subsidies from abroad acquire such influence and projection in large parts of the world over an extended period of time? There is no single answer to this query, though a few of the responses are well known.
First, the iconic images of the young, bearded, olive-clad fighters coming down from the mountains captured the imagination of many throughout the world, and the ensuing reversals of fortune their regime endured, including the subservience to Moscow for nearly 30 years, did not erase that original virtue.
A second possible account rests on the revolution's ostensible accomplishments in social policy, particularly in health and education. In this region and other parts of the world, results in these fields over the past half century have been generally considered insufficient or downright dismal. But apparent Cuban successes allowed its admirers to sustain a simple yet conclusive argument. The regime may be repressive and anti-democratic, depend heavily on external subventions because of its malfunctioning economy, but despite a decades-long American economic embargo, it at least achieved what few others did: dramatic improvements in health and education metrics. This in itself, for socially-minded, progressive souls, was-and still is-reason enough to back and admire the regime.
It did not matter a great deal that neither account was entirely accurate. Over the past 60 years, most Latin American societies-the exceptions being parts of Central America, Haiti and Bolivia-made enormous strides in both education and health. The average length of schooling reached 10 years in many countries, most of it free; universal literacy is a fact, again, in most of them; a growing share-often a third or more-of young men and women obtain some type of higher education. One can argue with the quality of the education they all receive, but that is another discussion.
Similarly with health: Vaccination is practically universal (and free), life expectancy has increased dramatically, infant mortality has dropped to very low levels, and some type of health care protection is available to large numbers (universal in Brazil, and more mixed numbers in Chile, for example). So, the Latin American performance over the years is not what many Cuban admirers believe.
On the other hand, the Cuban statistics are not entirely comparable. They are mostly not subject to international evaluation and comparison. For example, in education, Havana does not participate in the OECD's Programme for International Student Assessment, and UNESCO data often relies on reporting from Cuban authorities, rather than on standardized, internationally supervised tests. The same is true for its health indicators, often drawn from Pan American Health Organization or WHO statistics that ultimately rely on data collected by the Cuban government. That said, these doubts have scant bearing on the revolution's boosters' enthusiasm.
Lastly, and most importantly, however, the regime's initial popularity and persistent esteem-albeit now mainly among fringe groups-springs from another basic feature. It resides in a consistently nationalistic, or anti-imperialist as its supporters label it, attitude to the United States. While some may correctly view this as demagogic anti-Americanism, across Latin America, Europe and Africa, it is seen as a heroic, altruistic form of resistance to the worst evil the world has endured since World War II.
The Latin American and European left, the Non-Aligned Movement decades back (Fidel was its president in the late 1970s), the so-called Global South today, all include slices of public opinion and important sectors of the intellectual and political elites that are ferociously anti-American. They reject American interventions, from Guatemala, Cuba, the Dominican Republic, Chile, Panama and Venezuela, to the Congo, Vietnam, Iraq and most recently Iran. They also repudiate what they call Americanism or U.S. cultural influence, from McDonald's to jeans.
Their governments, whether left- or right-of-center, cannot translate these sentiments into foreign or economic policy: The dangers and costs are too high. But they can cheer someone else who dares to do so and is willing to pay the price (and in Cuba's case, an exorbitant one). Even today, Mexico, Brazil and Colombia, all oil exporters, accepted Donald Trump's ultimatum: If you send crude to Cuba, you'll face outrageous tariffs. They all caved.
If American civilization has extended all over the world, with the admiration, envy and grudging respect of billions of people, there continue to be sectors in each society-insofar as we can tell in countries like China-that strongly dislike what it represents. The Castros and Cuban Revolution have been a beacon for them since 1959, including today. For 67 years, their resistance in the face of American hostility-including the embargo-is, in the eyes of these sectors, exemplary.
***
In March the air-borne flotilla Nuestra América Convoy touched down in Havana from the United States and Europe; the sea-traveling supporters of the Cuban dictatorship sailed from different Mexican ports and docked in Havana harbor a few days later. Dozens of bearers of humanitarian aid, guitars, Che Guevara T-shirts and boundless enthusiasm for the solidarity they extended to the besieged regime were welcomed by the regime, as if a time capsule had traveled from the early 1960s to the second quarter of the 21st century. Jean-Paul Sartre, Simone de Beauvoir, Gabriel García Márquez and C. Wright Mills were not around, but their putative grandchildren might have been. Pablo Iglesias, a former leader of the Spanish left-wing group Podemos was there, Congresswoman Ilhan Omar's daughter was there, Greta Thunberg and Jeremy Corbyn were there, and Emma Fourreau, a representative of La France Insoumise, the French extreme-left party, also went.
The Cuban Revolution retains its hold on the imagination of Europeans, Americans and Latin Americans, with no other justification than the aggravated aggression put in place by Donald Trump. None of the pilgrims to the tropical Mecca would ever survive there for more than a few days with no electricity, gasoline, water, food, medicines or everyday necessities such as soap, toothpaste and toilet paper. Nor would any of them wish to live there. But like their predecessors more than 60 years ago, the seduction still worked. They were likely the last for whom Fidel's old trick still worked. Therein lies his lasting-and only-success.
2026 NEWSWEEK DIGITAL LLC.
This story was originally published May 27, 2026 at 5:00 AM.