Cuba’s communist regime was not supposed to live to see its 66th birthday. Yet Cuba is one of the world’s longest-surviving single-party states and the oldest in the Western Hemisphere. President Donald Trump and his team have all but said that they want to topple the government just as soon as he receives Iran’s “unconditional surrender.”
Have conditions and attitudes changed enough on the island since 1959 for the leadership and party to survive the next phase of America’s amped-up Monroe Doctrine?
Privation and pressure are nothing new in Cuba, but some periods are worse than others, and it’s instructive to recall one. Cuba’s “Special Period” was the grim decade following the collapse of the Soviet Union. I visited Cuba in the 1990s, and the experience was searing. With the dissolution of its patron state, Havana could no longer count on subsidized Soviet oil or a guaranteed market for its sugar. The crisis was immediate and visceral. I watched as Cubans, with a resilience born of necessity, abandoned their vehicles—late-model Ladas and Moskvitchs, 1950s Chevys and Fords—useless without gas, and turned to bicycles. Farmers hitched oxen to plows as tractors sat rusting in the fields for want of fuel and spare parts. Buses were actually passenger trailers pulled by transport trucks called camellos—camels—humped and hulking hot boxes stuffed with hundreds of passengers at a time.
Nights grew dark with rolling blackouts, the dreaded apagones. (The last place you wanted to find yourself was in an elevator.) Queues for meager food rations stretched for blocks, though freshly cut-and-crushed sugar cane provided abundant juice beside the cane fields, with no ice to make it refreshing. Moscow’s abandonment made it grim to believe in revolution as the Cold War ended.
A newly constituted Russia, struggling to feed its people, had no interest in propping up its Caribbean client. But the regime held. Cubans endured, their patience bolstered by Fidel Castro’s revolutionary cred. He framed the hardship as a noble struggle against imperialist forces. In Santiago de Cuba, the nation’s second-largest city, citizens got through it, making son Cubano music in the streets. Newly allowed, if heavily regulated, private restaurants served fare you could forage like rabbit or fish.
Years later, I made it back to Havana amid relative abundance and optimism. Barack Obama had reopened the U.S. Embassy, tourists spent dollars, and the small step toward normalization created unanticipated opportunities for private commerce to bloom amid the command-and-control economy—a private restaurant here, a hard-currency appliance shop there. Privately owned classic American gas-guzzlers had both spare parts and were running with near-full tanks.
Today, the crisis is back and worse. This is not just another chapter of hardship; I call it the “Extra-Special Period,” a convergence of pressures that could finally topple the regime. No exploding cigars, à la one of American intelligence’s more hapless and infamous ideas to knock off Castro. But this time, once again, the crisis has a Moscow connection.
Russia, mired in Ukraine, can’t play benefactor to far-flung allies when it’s emptying prisons and recruiting mercenaries for its war on Kyiv. Its capacity to project power in Venezuela, Syria, Iran, and Cuba is a joke. Putin finds himself leaning on North Korea, that prosperous economic superpower, for munitions.
Trump’s team perceives vulnerability and has its own domino theory. It starts with a weakened Venezuela that aligns with U.S. interests and is no longer permitted to supply Cuba with oil in exchange for medical assistance and security support. The Iran conflict has driven up the price of petrol in the open market, making it even harder to deliver fuel to the island.
Right now, it’s grim in Havana. Commercial airplanes are grounded due to a lack of jet fuel. Blackouts are back. But unlike the 1990s, the context is dangerously different.
Cubans under 40 have little memory of the 1990s, let alone Che Guevara and the revolution. Batista is a word in a textbook. They have less revolutionary patience. Their leader is not the charismatic, defiant Fidel, clad in battle fatigues, but a gray-suited successor without magnetism or iconic stature. This generation of Cubans is not isolated. The internet, though censored and slow, pierced the information blockade, connecting young Cubans to global democracy and a diaspora that fuels their discontent with viral anthems like Patria y Vida.
Furthermore, the cautionary tale of Venezuela looms large. Cubans have watched their once-wealthy ally descend into catastrophe, perhaps a terrifying preview of their own future. They’ve seen a corrupt, socialist system run out of other people’s money.
Into this volatile mix steps an administration teeming with ambition and short on humility. It is not lost on any Cuban citizen that Marco Rubio hails from their stock, a political boy wonder whose career is old-school anti-Castro. Republican presidents from Richard Nixon to Trump 1.0 sopped up the anti-Castro votes of South Florida Cubans but, in the end, had little interest in reliving the Bay of Pigs, the botched 1961 effort to topple the regime. But Rubio is not Henry Kissinger, Colin Powell, or Rex Tillerson, wary of regime change. For him, this is not just policy; it is a personal mission.
Rubio is the first Floridian secretary of state working for the first Floridian president. His crusade is rooted in his family’s familiar story of exile, but with a desire to rebuild a homeland only 90 miles away. For a secretary of state whose identity is linked to Cuba’s, bringing down the Western Hemisphere’s last socialist dictatorships (looking at you, too, Nicaragua) is a bracing cause, as invigorating as a cafecito with the exiles at Miami’s Café Versailles.
Biography can be destiny. For Eastern European ex-pats like Madeleine Albright and Zbigniew Brzezinski, freeing Eastern European captive states was always on their minds, but tempered by Council on Foreign Relations realism. Zbig, as Jimmy Carter’s National Security Advisor, loved arming the Afghans to stick it to the Soviets who conquered his native Poland but he would never try to invade Warsaw, the city of his birth.
By contrast, Rubio has one foot in the realist camp, a former chair of the Senate Select Committee on Intelligence. But as a Trump loyalist working with the likes of Steven Miller and Peter Hegseth, his regime-toppling side is in full force. Bearing this stick, Rubio’s team hopes to change Havana using the carrot of economic relief and opportunity. Credible fresh reports indicate secret meetings are ongoing with Raúl Castro’s inner circle.
They talked to Maduro, too. He went “the hard way.”
Havana is weak, hollowed out. It survived for decades on a cocktail of foreign patronage, nationalist propaganda, and brutal repression. But today, the patronage is drying up, the propaganda no longer resonates, and the repression is being met with a defiance amplified by technology. Trump’s expressed desire is for Cuba “to fall very soon” As with Iran, there’s no apparent democratic successor at the ready.
In this Extra-Special Period, external realities and internal decay may achieve what decades of boycotts and pressure have not. The fissures in the Cuban regime’s brittle foundations are visible. It’s feeling like something is about to break.
