The news arriving from Havana these days feels starkly different than the cautious optimism I remember. Reports of widespread power outages, a crippled economy, and now, talk of a potential U.S. Intervention under the Trump administration, are a jarring echo of a past many hoped had been left behind. The situation, as reported by CNBC, is dire: an oil shortage pushing Cuba to the brink, coupled with increasingly bellicose rhetoric from Washington. It’s a far cry from the tentative steps toward normalization I witnessed during a decade of reporting from the island, and it’s brought a wave of memories flooding back.
I first landed in Havana in March 2012, tasked with covering Pope Benedict XVI’s visit. Even then, the layers of bureaucracy were immediately apparent. As a journalist, securing permission to report felt like navigating a maze, repeatedly explaining our credentials to immigration officials. Thankfully, my team’s Spanish skills proved invaluable. But beyond the logistical hurdles, there was a palpable sense that something was shifting. The city itself, with its faded pastel buildings and a remarkable fleet of meticulously maintained classic American cars, felt like stepping back in time – a time that, even then, seemed poised for change.
A Brief Opening
For more than 50 years, Cuba and the United States had been locked in a geopolitical standoff. The 1959 revolution, led by Fidel Castro, brought a communist government to power just 90 miles from Florida, and quickly aligned the island with the Soviet Union. The subsequent seizure of U.S. Property and businesses led to a full U.S. Embargo in 1962, a policy that would severely restrict the flow of goods, fuel, and essential supplies to Cuba for decades. But by 2012, a subtle thaw was beginning. The Pope’s visit felt less like a religious pilgrimage and more like a symbolic gesture, a signal that dialogue might be possible.
Between 2012 and 2016, I made ten trips to Cuba, field producing for CNBC with correspondent Michelle Caruso-Cabrera. Each visit seemed to coincide with a significant moment, a potential turning point. We were invited to speak with the central bank governor, to meet with small business owners cautiously navigating a changing economic landscape. We even ventured off the official itinerary to Hershey, Cuba – a town built by Milton Hershey to secure a sugar supply for his chocolate empire – a poignant reminder of the island’s pre-revolution American ties. The repurposed Coca-Cola factory and the Western Union building now housing the country’s telecom company spoke volumes about a history both severed and stubbornly present.
The Promise of 2015
The real momentum began in July 2015, when President Barack Obama announced the restoration of diplomatic ties. The announcement triggered a flurry of activity. We quickly moved from Latest York to Miami, then onto a charter flight to Havana. The atmosphere on the ground was electric, though tempered with a characteristic Cuban caution. Hope was palpable, but it was a carefully guarded hope. People were excited, but wary of getting their expectations too high.
A month later, the U.S. Embassy reopened for the first time in more than 50 years. I watched the flag raising from a crumbling apartment building across the street, a small detail that felt monumental. For younger Cubans, in particular, it represented a potential future filled with opportunity, access, and choice. Obama’s subsequent visit in March 2016 only amplified that feeling. Travel restrictions were relaxed, and limited trade began to resume. While the embargo remained legally in place, its grip loosened, allowing a trickle of commerce and tourism to flow.
That week in Havana was remarkable. The Rolling Stones played a historic concert, and Major League Baseball held its first game on the island in years. Even amidst the excitement, there was a sense of restraint. Cubans had learned to be pragmatic, to remember how quickly things could change. Many questioned whether the United States truly intended to engage with Cuba without demanding significant political reforms.
A Shift in the Wind
By 2016, the changes were becoming visible. Carnival Cruise Line, through its Fathom brand, made the first U.S. Cruise ship visit in nearly four decades. JetBlue launched direct flights from New York. For a time, it genuinely felt like the barriers were coming down. Reporting, however, remained challenging. Permits could be revoked at the last minute, phone service was unreliable, and Wi-Fi was a rare commodity. Restaurants often presented elaborate menus, only to inform you that rice and beans were the only option. The contrast between the elegant facades of buildings and their crumbling interiors was a constant reminder of the island’s economic struggles.
Yet, even amidst the hardship, signs of transformation were emerging. Family-run restaurants, known as *paladares*, began to flourish in people’s homes. Airbnb listings proliferated. It wasn’t a dramatic overhaul, but it was a tangible shift.
My final trip came in November 2016, shortly after the death of Fidel Castro. While he had ceded power to his brother Raúl years earlier, Castro’s passing was a watershed moment. Havana fell silent. Music stopped, alcohol disappeared, and the city entered a period of formal mourning. It felt like an ending, but within Cuba, it was more complex than that.
Standing there, I sensed the energy of the previous years dissipating. The same questions resurfaced: What now? What would become of the reforms? What would be the future of U.S.-Cuba relations? Leaving Cuba that last time, I felt I had witnessed something rare – a brief period when history seemed to accelerate, when long-standing patterns loosened, and the future felt, for a moment, open.
In the years since, that momentum has stalled, and in some cases, reversed. The U.S. Withdrew embassy personnel, new travel restrictions were imposed in November 2017, and the flow of American visitors dwindled. The opening that once felt within reach has given way to familiar tensions, now exacerbated by the current crisis and the increasingly aggressive rhetoric emanating from Washington. As CNBC reports, President Trump has even alluded to a “friendly takeover,” raising serious concerns about the island’s sovereignty.
History in Cuba doesn’t always follow a linear path. It often circles back on itself. What comes next between these two nations remains unwritten, but the current trajectory is deeply unsettling. The situation demands careful observation and a commitment to understanding the complex realities on the ground.
The immediate future hinges on the evolving geopolitical landscape, particularly the ongoing conflicts in Venezuela and Iran, and the impact of the U.S. Oil embargo. The next key development to watch will be the outcome of ongoing diplomatic efforts, if any, to address the energy crisis and prevent further escalation.
What are your thoughts on the current situation in Cuba? Share your perspectives in the comments below.
