The United States and Cuba: A Complex History Reaches Another Crossroads

A New Chapter in an Old Rivalry

While the world’s attention has been fixed on international conflicts in the Middle East, a potentially explosive situation has been quietly brewing much closer to American shores. In mid-April, President Trump made headlines when he cryptically suggested that the United States might “stop by Cuba” after dealing with Iran. This wasn’t just casual rhetoric. The Trump administration has effectively choked off nearly all oil shipments to the island nation, pushing Cuba’s already fragile economy to the brink of total collapse. Behind closed doors, high-level negotiations between the two countries are underway, though details remain scarce. What is clear, however, is Trump’s bold declaration that he believes he’ll have “the honor of taking Cuba” – a statement that has left many wondering what exactly he means. For nearly seven decades, this small island just ninety miles from Florida’s coast has cast an enormous shadow over American foreign policy, punching far above its weight in terms of international significance. The current crisis represents yet another dramatic turn in a relationship that has never been simple, never been easy, and has profoundly shaped both nations in ways that continue to reverberate today.

The Paradise That Never Was

To understand today’s tensions, we need to rewind to the 1950s, when most Americans viewed Cuba through rose-colored glasses as nothing more than a hedonistic tropical playground. Jorge Malagon Marquez, a Cuban-American history professor at Miami Dade College, describes it as a place “where anything goes, where there are casinos, where there’s prostitution,” and to a large extent, that reputation was well-earned. Hollywood celebrities like Frank Sinatra would jet down for weekends of partying, gambling, and indulgence. For many Americans, Cuba was synonymous with exotic fun in the sun, a convenient escape from the conformity of 1950s American life. But this glamorous image was dangerously incomplete. What American tourists didn’t see – or chose to ignore – was the deep dissatisfaction simmering beneath the surface among ordinary Cubans who were living entirely different realities. Many Cuban citizens were barely subsisting, laboring in industries that were outright owned and controlled by American companies. As Professor Marquez explains, “Cubans loved Americans coming as tourists or what have you, but it was the control of the economy that really bothered them.” This economic domination was made even more bitter by historical memory: when the United States “freed” Cuba from Spanish rule after the Spanish-American War in 1902, the independence granted was severely limited. Marquez compares it to the independence he gave his teenage children – “Sure, you’re independent, so long as you’re home by 10 o’clock.” Cuba was technically sovereign, but the United States maintained the right to intervene militarily whenever its interests were at stake, a right it exercised repeatedly until the 1930s. By the late 1950s, decades of economic exploitation and political interference had created the perfect conditions for revolution.

The Rise of Castro and the Cold War’s Longest Shadow

While many Latin American countries harbored similar grievances against American intervention, Cuba became something different – the only long-lasting communist dictatorship in the Western Hemisphere. What made the difference? According to Professor Marquez, it was “Fidelismo” – a cult of personality centered on one man that transcended ordinary political ideology. “If it had been anybody else, this would’ve fizzled out within the first couple of years,” he notes. Fidel Castro seized power in 1959 and immediately transformed from a bearded revolutionary into a central figure in the global Cold War. His communist revolution sparked American fears that similar movements would spread throughout the Americas like dominoes falling. Castro’s authoritarian regime proved remarkably resilient, surviving challenge after challenge: a comprehensive trade embargo that has now lasted over six decades, the terrifying Cuban Missile Crisis that brought the world to the brink of nuclear annihilation, and even the collapse of the Soviet Union, which had been Cuba’s primary patron and economic lifeline. Marquez himself experienced the power of Castro’s personality cult firsthand as a five-year-old in Cuba. He recalls being part of the “Pioneers for the Revolution,” children who wore red scarves and participated in disturbing exercises designed to replace religious faith with loyalty to Castro. In one exercise, teachers would have children bow their heads and pray to God for candy – and when no candy appeared, they would be told to ask Fidel for candy instead. Miraculously, candy would then appear. “I wish I were making this up!” Marquez exclaims. Such indoctrination was systematic and pervasive. In 1967, Marquez and his family joined the flood of refugees fleeing the island, becoming part of the more than 1.5 million Cubans who have sought freedom in the United States since the early 1960s.

The Bay of Pigs and the Making of Cuban-American Politics

The exodus from Cuba brought to America not just refugees seeking a better life, but people carrying deep political grievances that would reshape American politics, particularly in Florida. Among those who fled were Elsa and Becky Cobo, whose father Arturo witnessed firsthand the brutality of Castro’s revolution. As a teenager in Havana in 1960, Arturo watched as military forces stormed his father’s bank, literally taking the keys from his grandfather’s hands and ordering him to leave. “That’s when he said, ‘We gotta do something,'” Elsa remembers. Arturo escaped to the United States and enlisted in a CIA-trained brigade of Cuban exiles preparing for a secret operation to overthrow Castro. In April 1961, this force landed at Cuba’s Bay of Pigs, expecting American air support that would ensure their success. At the last minute, President John F. Kennedy, a Democrat, withdrew that support, leaving the exile forces stranded and vulnerable. “They were basically left there to die,” says Elsa, the betrayal still raw in her voice decades later. This abandonment had profound political consequences that echo to this day. When asked why Cuban-Americans are so overwhelmingly Republican, Professor Marquez’s answer is simple and direct: “Bay of Pigs. That’s it. You don’t have to go further than that.” The perception that a Democratic president had betrayed Cuban freedom fighters created a political allegiance that has defined Cuban-American voting patterns for generations. Arturo Cobo spent nearly two years in a Cuban prison as a result of the failed invasion. After his release, he settled in Key West, Florida, where he dedicated himself to helping wave after wave of refugees arriving from Cuba, many barely surviving the perilous ninety-mile crossing.

Desperate Journeys and a Community in Exile

The desperation of those who risked everything to escape Castro’s Cuba is preserved at the Key West Botanical Garden, where makeshift rafts used by refugees are displayed as stark testament to human determination. These crude vessels, some made of little more than Styrofoam and hope, carried people across treacherous waters where many met their deaths. The Cobo sisters’ father devoted his life in America to assisting these desperate arrivals, never forgetting his own journey to freedom. These successive waves of migration fundamentally transformed South Florida, creating vibrant Cuban-American communities in Miami and beyond. But as Professor Marquez points out, this exodus also inadvertently strengthened Castro’s grip on power back in Cuba: “Those that would have been willing to rise up? Gone. I mean, you gotta give it to Fidel Castro. He was brilliant, you know, in a sort of, like, evil way. He was the evil genius.” By allowing – even encouraging – his opponents to leave, Castro eliminated potential resistance without firing a shot. Arturo Cobo died in 2019, like countless other exiles, never returning to his homeland and never seeing the free Cuba he had fought for. “They came over hoping that one day Cuba would be free,” says Becky, “and never imagined… they would not see the day that that would happen.” The sorrow in that realization is compounded by the knowledge that their absence from Cuba may have been exactly what allowed the regime they fled to endure for so long.

Today’s Crisis and an Uncertain Future

Fidel Castro died in 2016, and the Cold War that gave context to so much of the U.S.-Cuba conflict ended decades ago. Few serious analysts believe Cuba poses anything like the threat it once represented to American interests. The Cuban economy, which never functioned well under communist central planning, has been in absolute freefall since the COVID-19 pandemic, with nearly one-fifth of the remaining population leaving the island since 2021. The country that once positioned itself as a beacon of socialist possibility has become a failed state, dependent on foreign assistance and oil shipments from dwindling allies like Mexico and Russia. Into this situation of humanitarian crisis, the Trump administration has chosen to apply maximum pressure, blocking virtually all oil shipments and worsening conditions for ordinary Cubans. President Trump’s statement that “whether I free it, take it, I think I can do anything I want with it” has created tremendous uncertainty about what comes next. On both sides of the Florida Straits – in Miami’s Little Havana and in Havana itself – Cubans are watching and waiting, uncertain whether they’re witnessing the final chapter of the Castro regime or the beginning of something potentially worse. For the families who fled decades ago, for the community they built in America, and for those who remained on the island, the question remains the same one that has haunted this relationship for nearly seventy years: what will Cuba’s future look like, and what role will America play in shaping it?