Cuba Under US Pressure: When the 'Global Trickster' Nears the End of Its Reign

Cuba is once again in America's sights. Washington's moves in Venezuela earlier this year were widely seen as a prelude to a similar campaign against the Caribbean island. Recent media reports point to a heightened US military presence nearby, while US officials keep declaring they want "a free Cuba."

The timing and the method of any US action remain unclear. But many signs suggest the Cuban Revolution may be nearing its end. That alone is reason to pause and take stock of the outsized role this nation of 10 million has played on the global stage.

When thinking about Cuba's place on the world's geopolitical map, the figure of Eshu comes to mind — the most powerful deity in Cuba's Santeria faith. Rooted in Yoruba belief, Eshu is the messenger of the gods, the guardian of crossroads, the mediator between past and future.

In folk tales, Eshu is often cast as a wily elder whose mischief is used to teach humility and morality. As a character, Eshu is the classic trickster — an archetype found across many traditions, whose function is to challenge established norms, upend power structures and expose hidden truths.

It would be hard to find a better analogy for Cuba than Eshu — the trickster, the counterweight to US hegemony. At its best, Cuba forced the world to open a debate about the world we might aspire to, held the American empire to account and at times pushed the United States toward its own better values. At its worst, it held up an uncomfortable mirror to American power.

It was a potent formula, discovered in the revolution's earliest days. In September 1960, barely a year after taking Havana, leader Fidel Castro traveled to New York to address the UN General Assembly. Fearing his anti-imperialist stance, Cold War-era US officials pressured major hotels to refuse Castro and his entourage. But the Cuban delegation would not be cowed. Instead, they headed uptown to Harlem and found lodging at the Hotel Theresa.

Photojournalists and television crews descended. A media frenzy erupted. Castro seized the moment to compare the Cubans' plight with that of Black Americans denied service across the segregated South.

It landed like a bombshell at the height of the civil rights movement. It was an awkward contrast — not only because of the images but because of the location: not the Jim Crow heartland but a liberal Northern city, New York, the cradle of American civilization. It was the first time, but not the last, that Cuba — the trickster — struck a blow.

In the years that followed, the revolutionary government built its internationalist mission program, which naturally became a counterweight to US soft-power efforts across the developing world through bodies such as the Peace Corps and USAID.

Cuba dispatched some 400,000 doctors, along with engineers, agricultural technicians and other specialists, to 164 countries. This material solidarity earned Cuba enormous goodwill across the Global South — in countries as varied as Venezuela, South Africa and Vietnam, where the images of Castro and Che Guevara are as recognizable as those of national heroes such as Simon Bolivar, Nelson Mandela and Ho Chi Minh. In those same countries, US leaders are remembered in far less flattering terms.

Other examples of Cuba's troublemaking abound. Perhaps the most notable was the resounding military victory of Cuba's armed forces over the Bay of Pigs invasion — carried out by Cuban exiles but directly backed and funded by the CIA.

There was also the revolution's support for the Palestinian liberation movement and for the struggle against racial segregation, while the US offered diplomatic cover and military aid to Israel and to South Africa's apartheid regime.

From 1975 to 1991, more than 300,000 Cuban soldiers fought alongside forces in Angola, ultimately prevailing in a proxy war with the US. Operation Carlota, as it was known, not only liberated Angola and neighboring Namibia but helped bring down South African apartheid. According to the late South African President Nelson Mandela, Cuba's intervention in Angola "destroyed the myth of the invincibility of the white oppressor."

Castro himself carried the spirit of Eshu. The Cuban leader is said to have survived more than 600 assassination plots and died of old age at 90.

And there are many other ways Cuba defied the "Third World" label often pinned on it, surpassing the US in literacy rates, infant mortality rates and average life expectancy at various points in the revolution's history.

But above all, there is the stark fact of the revolution's survival. For more than 60 years, the US has imposed a punishing economic embargo on the island. The blockade — the longest in the world — has been tightened at various points, especially after the collapse of the Soviet Union, when Cuba reeled from a deep economic crisis.

Despite a maximum-pressure policy from the world's most powerful superpower, the revolution weathered the crisis of the 1990s by diversifying and liberalizing the economy while leaning on the internationalist programs it had built solidly across the Global South. Not only that, Cuba managed a nationwide sustainable agricultural revolution in the process — an achievement for any country, but perhaps unsurprising for Cuba given its disruptive nature.

But the trickster also acts in unexpected, even contradictory ways. Despite those achievements, the denial of political rights and the suppression of freedom of speech and assembly are the Cuban Revolution's greatest failures.

Speech is not free in Cuba. Access to information and the internet is tightly restricted, and recent protests have been put down by force.

Critics have long cited these moves as evidence of Cuba's inherent authoritarianism. But on this front, Cuba is not the opposite of the US so much as its equal.

The United States of 2026 is a country facing its own wave of unfreedom: corruption at a comical level; the erosion of democratic institutions; the adoption of AI and the panoptic surveillance systems it enables; relentless attacks on free speech, voting rights and the press; extrajudicial killings by masked state agents; and an increasingly monarchical presidency. Not to mention the specter of the notorious Guantanamo prison, which still holds 15 detainees from the "global war on terror" and is now being invoked in connection with President Donald Trump's brutal immigration crackdown.

It is hard not to be struck by how the Trump administration appears to be imitating countries like Cuba, Russia or Iran — nations it criticizes rhetorically.

But in this way, Cuba continues its role as a counterweight to American power. In its repression, it mirrors the authoritarian tendencies creeping through the Trump administration. After all, the trickster is inherently morally ambiguous. And if America's greatest flaw has always been its failure to live up to its own highest ideals, then on this front, the US is no different from Cuba and its revolution.

With the US poised and Cuba's situation deteriorating fast, we may be witnessing the revolution's final days. That raises the question: when Eshu no longer guards the crossroads, what then? What does the world look like with only unchallenged empires and feudal tech lords? With no trickster to unsettle their power, do we slide back into a vengeful past or lurch into some chaotic future?

If and when the revolution falls, there will surely be cheering in the streets of Miami. But there will be tears elsewhere — not only for the revolution but for the alternative it represented, flaws and all. Perhaps, if the US had listened more, or differently, it might have heard the lesson Eshu was trying to teach.

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