Paul Conroy's Havana Diaries: Embargo Blues
With its recent flexing of military muscle, America is back on the world stage, rattling sabres with the confidence of a superpower that has never quite learned to stay its hand. Threats of intervention ricochet from Greenland to Iran, and one familiar name keeps resurfacing—Cuba, the long-standing Caribbean irritant, ninety miles off the Florida coast and still stubbornly red.
The question hanging in the heavy Havana air is no longer if pressure will come, but how much more the system can take. How close is the much-vaunted end of communism in this small, exhausted thorn lodged in the side of the American Goliath—and what, exactly, will be left standing when it finally gives way?
Havana, centuries of exquisite architecture and deep culture lie crumbling, starved of care and suffocating beneath a failed revolution, communist rule, and the long shadow of American embargoes. Paint peels. Stone flakes. Time itself feels rationed. Yet inside the central tourist district of old Havana, history’s damage is held at arm’s length, like a bad smell politely ignored.
The historical buildings are a palimpsest of colonial fingerprints: Spanish baroque façades and grand archways now tired and blistered, neoclassical touches and pastel colours whispering of a European age laid awkwardly over Caribbean heat. Every courtyard and balcony carries the same message—old elegance still clinging on, long after the money and care ran out.
Nothing captures the split-screen reality better than the Ambos Mundos Hotel. Its elegant façade of rich reds and clean stone once housed Ernest Hemingway, who declared it “a good place to write.” Inside, polished wood and an expensive bar hum with privilege. Outside, a slow-moving parade of affluent tourists stops just long enough to read the commemorative plaque before sweating tour guides herd them on, history consumed, box ticked.
In the narrow, shaded street nearby, a trumpet player picks out a tune from the Buena Vista Social Club—the perfect soundtrack to this carefully curated Havana. The postcard version: pink Cadillacs, rum, expensive cigars. Everything is calibrated for the shrinking number of tourists still allowed through the gates, Trump-era restrictions slamming shut the brief Obama thaw, selling those who make it in a carefully packaged illusion of the perfect Havana experience.
There’s little incentive to step beyond the gated calm of the tourist zone. But walk a few hundred metres down any of the narrow feeder streets and the city snaps back to life. The manufactured hush of colonial grandeur collapses into noise and motion: street vendors shouting, reggae rattling from battered ghetto blasters, barefoot kids flooding the pavement, fashioning toys from broken bicycle parts and sun-bleached plastic. Life—raw, improvised, and unlicensed—pushes its way back in.
Within half a mile, the scrubbed, on-show Havana has faded to a rumour. Buildings lean and sag, many on the brink, balconies propped up with jury-rigged timber, standing less through engineering than pure stubbornness. In places, whole buildings have been gutted from the inside, their façades left standing like stage sets, skeletal against the hard blue of the Caribbean sky.
Ad hoc mechanics colonise the pavements, torsos buried in open engines. The glossy pink classics are gone; what remains are relics kept alive past reason—battered shells that feel closer to garden sheds than vintage icons. On street corners, old women sit beneath parasols. At their feet, empty soft-drink bottles filled with petrol are sold by the litre to young men on whining two-stroke scooters.
Every so often you hit a snaking queue. Locals, slick with sweat, wait with practised patience. The prize is fresh bread—another basic commodity now worthy of a line. One teenager, improbably, has fallen asleep on his bicycle taxi, white rubber wellington boots stretched out, absurd in the crushing heat.
Images of Guevara and Castro are everywhere—but only where dollars circulate. They glare out from T-shirts and posters in high-priced tourist shops, revolutionary icons reduced to retail, priced exclusively in foreign currency.
Step outside that perimeter and they vanish. You’re no more likely to see communist heroes on the walls than you are to find portraits of Margaret Thatcher hanging in a Yorkshire pit town. The revolution does not decorate the spaces where people actually live. Whatever glories it once promised now exist only in the minds of those who imagined them. On the streets, there’s no mythology. Just life, stripped down to what works—and what survives.
In faded, peeling doorways, residents sit behind ancient wrought-iron gates, watching the street slide past. Some lay out small tables draped with lace cloths, selling whatever can be spared: mirrors, hairbrushes, chipped ornaments. Not souvenirs. Not nostalgia. Just excess carved from necessity. Anything that might scrape together a few extra pesos.
On every other street corner, mountains of rubbish rise up in slow, rotting heaps—another symptom of an infrastructure slipping into its death throes. From the shade, nursing a cold beer, I watch a procession of shambling, broken figures drift toward the overflowing steel bins. Plastic bags and empty bottles are knotted to their threadbare clothes like makeshift armour.
They rummage with practised urgency, hands disappearing into the stink, hunting for something edible. Then the realisation lands: someone else has already stripped the bins clean. A sigh, barely audible, and they shuffle away. Minutes later, another figure takes their place. The cycle repeats. Quiet. Relentless. Unnoticed.
It’s been over six wild decades since Fidel and Che rolled in and booted out Batista, installing one of the longest-running communist regimes on the planet. From day one, Cuba was on a collision course with its big, paranoid neighbour to the north. McCarthyism was frothing in the U.S., and Cuba cosying up to the Soviets poured fuel straight onto the fire. The Cuban missile crisis sent the temperature into the red. The Bay of Pigs fiasco—America’s botched coup attempt—ended in public humiliation for Kennedy’s White House and locked in decades of mutual hostility. As ever, it was ordinary Cubans who paid the price.
Sixty years of sanctions and embargoes have chewed Cuban society down to the bone. An estimated five million Cubans have risked the shark-infested ninety-mile stretch to the U.S.—close enough to taste, far enough to kill you. Those who stayed have endured a long, grinding descent, propped up by communist life support. First Moscow. More recently, Venezuela—Hugo Chávez’s discounted oil keeping the island’s heart beating for the past two decades.
Now, with Donald Trump pulling geopolitical stunts straight out of a pulp thriller—snatching Nicolás Maduro and turning oil into a choke collar—Cuba’s future looks like a bad trip with no comedown. Washington threatens to cut supplies, float a full maritime embargo, and Marco Rubio—the Cuban-American hardliner—publicly warns Havana’s leadership they should be “very worried.” For the average Cuban, the horizon is darkening fast.
With the drying up of the oil, comes the plague of power cuts, already a feature of everyday life, the lack of fuel means whole neighbourhoods are plunged into darkness up to twenty hours at at time. Those who can afford it turn to fume belching generators for power, those who can’t fall back on the time-honoured candle for their light. The lights are rarely off in the tourist district.
I meet Antonio, a 64-year-old stone mason whose face reads like a case file—every crease carved by hard years. He grins anyway, pointing proudly at one of the elegant buildings he once repaired. “I fixed that stone,” he says. “Then I fell. Broke my hip.” He shifts on the park bench, wincing.
I ask what he thinks of the men still running the country. He’s unusually blunt. Cubans learned long ago that honesty carries risk.
“They don’t give a shit,” he says, shrugging, as casually as commenting on the weather. “This is the Caribbean. We’re ninety miles from America. This should be paradise—like the Bahamas.” He pauses. “Instead, we have shops full of nice things you can only buy with dollars. We don’t have dollars. We have pesos.” He taps his pocket. “Pesos buy nothing.”
“Maybe,” he says, optimism briefly breaking through the fatigue, “in one year we have a change of government and life is better.” Then another thought catches. “This is a good country. You are safe here. Cubans will not rob you. We like guests.”
He’s right. Wandering Havana’s backstreets, I’ve never felt threatened or sized up—not like Rio, Santiago, or Buenos Aires. Despite the vast gulf in wealth, there’s none of the hard resentment inequality usually breeds. Just people carrying on, open-faced, making room for strangers in a city that has learned how to endure.
Behind gates and courtyards, in old villas and haciendas, the Cuban elite remain insulated from the grind. They never feel the bone-breaking arithmetic of survival. Outside those walls, most people live on improvisation and grit, fuelled by humour, resilience, and a stubborn refusal to collapse—even as everything around them threatens to do exactly that.
As if sanctions and daily deprivation weren’t enough, more bad news arrived from within on Sunday night. The still-powerful regime approved measures to declare a state of war, citing rising tensions with the United States, and began pushing the language of general mobilisation—what they call “a war of all the people.”
For a population already stretched to breaking point, it was another tightening of the vice, another reminder that in Cuba the pressure doesn’t just come from abroad—it’s applied at home too.
On the walk home I take the seafront—the Malecón—a sea-battered ribbon of crumbling concrete where Havana slams head-on into the Atlantic. Apart from a handful of young men
fishing in the gentle swell, it’s almost deserted. The four-lane road is empty too, save for the occasional neon-pink Cadillac ferrying the same predictable, badly dressed tourists back to their air-conditioned resorts, Havana’s last reliable cash crop.
As the final light drains from the sky, I pass a solitary figure perched on the stone sea wall. A girl—fifteen, maybe sixteen—stares out toward the darkening horizon, arms wrapped tightly around her knees. Against the bruised blues of sea and sky, her stillness carries a quiet gravity. There’s a sadness there you can almost touch.
Like all of Cuba, I imagine she’s looking toward a better future somewhere out beyond that vast stretch of water. How long she’ll have to wait is, like everything else here, impossible to say.
