Opinion

Losing Cuba, the global trickster

The Cuban Revolution, with all its contradictions, has given plenty to the world. Its fall will be a major loss.

By Mario Reinaldo Machado

Lecturer at Dartmouth College.

19 Oct 2026

Cuban President Fidel Castro and South African leader Nelson Mandela gesture during the celebration of the “Day of the Revolution” in Matanzas on July 27, 1991 [File: AP]

Cuba is once again in the United States’s crosshairs. Washington’s operation in Venezuela at the start of the year is largely seen to have paved the way for a similar undertaking on the Caribbean island. Recent media reports have revealed US military activity nearby while US officials have repeatedly said they want “Cuba to be free”.

When and how the US may strike is still unclear. But indications are that the Cuban Revolution may be nearing its end. That is reason enough to pause and reflect on the outsized role this nation of 10 million has played on the world stage.

When thinking of the Cuban presence on the global geopolitical scene, the figure of Eshu, the most powerful spirit in Cuban Santeria comes to mind. Derived from the beliefs of the Yoruba people, Eshu is a divine messenger, the guardian of the crossroads and mediator between the past and the future.

In stories, Eshu is often portrayed as a mischievous elder, one whose antics are used to teach humility and morality. As a character, Eshu is a classic trickster, an archetype commonplace to many traditions that functions to challenge established norms, subvert power structures and reveal hidden truths.

It’s hard to imagine a more apt analogy for Cuba than Eshu, the trickster, foil to US hegemony. At its best, trickster Cuba forced an open debate on what kind of world we might aspire to and held the empire to account, at times even pushing the US towards its better angels, however begrudgingly. At its worst, it held up an uncomfortable mirror to US power.

It is a potent formula, one struck upon from the very earliest days of the revolution. In September 1960, just a year after taking Havana, Cuban leader Fidel Castro found himself visiting New York to address the United Nations General Assembly. Wary of his anti-imperialist rhetoric, a Cold War-obsessed US government put pressure on several prominent hotels to refuse service to Castro and his entourage. But the Cubans were not to be deterred. Instead, they went uptown to Harlem and found a place at the Hotel Theresa.

Photographers and TV camera people flocked there. A media sensation ensued. And Castro used the opportunity to draw comparisons between the plight of the Cuban delegation and that of Black Americans being refused service in the segregated South.

This landed like a bomb in the middle of the burgeoning civil rights movement. It was an awkward contrast, not just because of the optics but because of the location, not in the heart of Jim Crow, but in a liberal northern city, New York, the cradle of American civilisation. This was the first, but not the last time that Cuba, the trickster, would strike.

In the following years, the revolutionary government developed its programme of Cuban Internationalism, which inevitably stood as a counter to US soft power efforts in the developing world through organisations like the Peace Corps and USAID.

Cuba would send as many as  400,000 doctors, not to mention engineers, agricultural technicians and other professionals, to 164 countries across the world. This material solidarity garnered great affection for Cuba among many countries in the Global South, countries as disparate as Venezuela, South Africa and Vietnam, where characters like Castro and Che Guevara are as recognisable as national heroes like Simon Bolivar, Nelson Mandela and Ho Chi Minh. In these same countries, American leaders are remembered too, often in far less flattering terms.

Other examples of Cuba’s trickster antics abound. Perhaps most notable is the Cuban armed forces’ sound military defeat of the Bay of Pigs invasion, which, while carried out by Cuban exiles, was supported and funded directly by the CIA.

There is also the revolution’s support for the Palestinian liberation movement and the antiapartheid struggle even as the US provided diplomatic cover and military aid to Israel and the apartheid regime in South Africa.

From 1975 to 1991, more than 300,000 Cuban soldiers fought alongside forces in Angola, eventually emerging victorious in a proxy conflict with the US. Operation Carlota, as it was called, would not only liberate Angola and neighbouring Namibia, but it would precipitate the downfall of South African apartheid as well. According to former South African President Nelson Mandela, Cuba’s intervention in Angola “destroyed the myth of the invincibility of the white oppressor”.

Castro himself has carried the spirit of Eshu. The Cuban leader reportedly survived more than 600 assassination attempts and died of natural causes at the age of 90.

And there are the many ways that Cuba has defied the “third world” label so often foisted upon it by beating the US in literacy rates, infant mortality and life expectancy at various points in its revolutionary history.

But beyond all of this, there is the sheer fact of the revolution’s survival. For more than 60 years, the US has imposed a severe economic embargo against the island. The embargo – the world’s longest – has been intensified at various points, specifically after the fall of the Soviet Union as Cuba reeled from a profound economic crisis.

Despite this regime of maximum pressure from the world’s largest superpower, the revolution nevertheless persevered through the crisis of the 1990s by diversifying  and liberalising the economy and by drawing upon its well-established programme of internationalism in the Global South. Not only that, but it managed a nationwide sustainable agricultural revolution in the process, a feat for any nation, but perhaps unsurprising for Cuba, given its trickster nature.

But tricksters also work in unexpected, even contradictory ways. Despite these accomplishments, the denial of political rights and the repression of the freedoms of expression and assembly have been the Cuban Revolution’s greatest failings.

Speech is not free in Cuba. Access to information and the internet is heavily restricted, and recent popular protests have been violently extinguished.

Such dynamics have long been pointed to by detractors as evidence of Cuba’s inherent authoritarian nature. But in this regard, Cuba is not the US’s opposite, but rather its peer.

The US in 2026 is a country facing its own rash of unfreedoms: comical levels of corruption; the erosion of democratic institutions; the embrace of AI and the panopticon surveillance it enables; continual attacks on free speech, voting rights and the media; extrajudicial killings of US citizens by masked agents of the state; and an increasingly monarchical presidency. All of which is to say nothing about the spectre of the infamous detention facility at Guantanamo Bay, still home to 15 detainees from the “global war on terror”, raised once more in relation to President Donald Trump’s brutal immigration crackdown.

One cannot help but be struck by the ways that the Trump administration appears to emulate countries like Cuba or Russia or Iran that it rhetorically maligns.

But in this way, Cuba carries on in its role as the foil to American power. In its repression, it reflects the creeping authoritarian inclinations that characterise the Trump administration. Tricksters, after all, are themselves morally ambiguous. And if the greatest flaw of the US has always been that it fails consistently to live up to its most laudable ideals, then in this sense, it is no different to Cuba and its revolution.

With the US poised and ready and with the conditions in Cuba deteriorating rapidly, we may be witnessing the final days of the revolution. That begs the question: When the day comes that Eshu no longer guards the crossroads, what then? What becomes of the world when there is nothing but unquestioned empires and techno-feudal overlords? Without tricksters to confound their power, will we revert to the revanchist past or tumble into some kind of dystopian future?

If and when the revolution finally falls, there will no doubt be cheering on the streets of Miami. But there will be tears elsewhere – tears not just for the revolution, but for the alternative that it represented, however flawed. Perhaps if the US had listened more or differently, they would have heard the lesson that Eshu was trying to teach.

The views expressed in this article are the author’s own and do not necessarily reflect Al Jazeera’s editorial stance.