Why Is America So Obsessed With Cuba?

Foreign Policy · Feb 26, 2026 · Collected from RSS

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My first visit to Cuba, in 1990, came at what then seemed like the darkest hour of Fidel Castro’s rule. The reformist Soviet president, Mikhail Gorbachev, had recently traveled to Havana to inform Castro that the decades-long period of Moscow helping to keep the Cuban economy afloat through generous subsidies and barter trade arrangements was ending. Gorbachev had his hands full with a crisis-ridden economy back home and could no longer afford to play the generous patron to a distant ideological ally. My first visit to Cuba, in 1990, came at what then seemed like the darkest hour of Fidel Castro’s rule. The reformist Soviet president, Mikhail Gorbachev, had recently traveled to Havana to inform Castro that the decades-long period of Moscow helping to keep the Cuban economy afloat through generous subsidies and barter trade arrangements was ending. Gorbachev had his hands full with a crisis-ridden economy back home and could no longer afford to play the generous patron to a distant ideological ally. The effects of Moscow’s sharp change of course rippled through every facet of life on the island. Big industrial projects were mothballed, including a half-built nuclear power plant. As Cubans were forced to tighten their belts, imported foodstuffs disappeared from shelves, and gasoline—long supplied by Russia at a steep discount—became scarce. Over the next few years, returning to Cuba as often as I could, I observed as what had begun as a kind of death watch for the Castro era turned into something else entirely: The Cuban state and the Cuban people both made a series of grueling adjustments during this time, known as the “special period,” and before long, talk of a collapse morphed into a make-do economy centered on survival. That experience has made it hard for me to watch Washington revive the fantasy that Cuba is just one shock away from collapse and that U.S. pressure can deliver the decisive blow. Outside of south Florida, which is home to the island’s largest diaspora, Cuba has rarely figured in U.S. news coverage since President Barack Obama’s visit to the country in 2016. Yet now, with the overthrow and abduction of Cuba’s most important remaining benefactor—Venezuelan President Nicolás Maduro—a new kind of death watch for the system that Castro built has been launched in U.S. media. Were it not for the Trump administration’s massing of U.S. might for its latest military adventure in Iran, one could suspect that the countdown for the end of Cuba’s socialist system would be ticking loudly. As I have followed the Trump administration’s rhetoric about Cuba, with it hinting strongly at the need for capitulation, and watched it cut off desperately needed oil to the island from Venezuela and Mexico, my mind has returned to my visits there and my years of observing Cuban foreign policy from afar. The question that won’t go away is this: What has Cuba done to deserve so much U.S. hostility, and even spite, from the time of the country’s revolution in 1959 until now? Some readers may recoil at the question, equating it with ideological sympathy for a regime that has imposed generations of hardship on its own people and made grave and gratuitous mistakes in the management of its economy. It is undeniable that the Castro system has all but banned opposition parties, independent labor organizations, dissent, and free speech. I witnessed this up close during my years covering Cuba, when courageous, independent-minded activists were arrested after granting me interviews, and even the smallest-scale gestures pushing for political freedom were deplorably snuffed out. During one visit, I was summoned by the foreign ministry for covering citizen activism and expelled from the country. It is no defense of an unfree regime to ask why, in a world full of countries where governments systematically violate citizens’ rights, the United States has maintained economic sanctions against Cuba for decades, and why it now appears eager to topple the Cuban government altogether. Furthermore, what, besides might, gives the United States the right? The United States has its own long and scarcely examined history of siding with regimes that gravely violate the rights of their citizens. There are plenty of recent examples from African countries, where regimes—such as Rwanda’s government under President Paul Kagame—imprison or assassinate critics and organize implausibly uniform victories at the polls, showing nearly universal support for their rule. Closer to Cuba, governments allied with the United States in Central and South America have organized murderous disappearance campaigns against opponents spanning decades. Most recently, in Venezuela, Maduro was removed while many of the officials who oversaw his system of repression and corruption remain in place. In Asia, meanwhile, Trump has established affectionate personal ties with North Korean leader Kim Jong Un, whose dictatorship is far more oppressive than Castro’s. Trump has also shown sympathy and admiration for stern authoritarians of larger countries such as China and Russia. It has long been commonplace in U.S. political rhetoric about Cuba to point out that it is one of very few countries that still cling officially to communism—placing it on the “wrong side of history,” to use a popular truism. Let’s briefly consider this phrase. For all of Cuba’s faults, its government supported African liberation from colonial rule and fought against the domination of parts of the continent by apartheid-ruled South Africa. For many Africans, Cuba’s troop presence was not an act of Soviet adventurism, as it was labeled in Washington, but of anti-colonial solidarity. In most of these conflicts, the United States supported Pretoria. Cuba has similarly deployed doctors in poor countries around the world to deliver health care to populations under-supported by multilateral institutions such as the World Bank and bilateral Western aid. This is to say that if one is to draw up a balance sheet, then it should at least be complete. Two possibilities stand out to explain the United States’ strong and persistent enmity. One of them is rooted in the distant history of the Cold War, and the other, although hardly new, is more recent. From the consistency of U.S. policy, it would appear that the United States has never overcome the humiliation of its own failures in Cuba. Over time, grievance has hardened into policy orthodoxy, reinforced by domestic electoral incentives that reward maximalism rather than strategic caution. Here, the bill of particulars is long, from the United States’ disgraceful support of the corrupt dictatorship of Fulgencio Batista, which Castro overthrew, to its failure to foresee or prevent Castro’s takeover in 1959, to the disaster of the CIA’s Bay of Pigs invasion in 1961, to the Cuban missile crisis of 1962. But history like this does not suffice to explain the persistence of official U.S. enmity. After all, Trump has shared toasts with North Korea’s Kim, whose grandfather fought the United States to a standstill in a costly war in the 1950s, and the United States maintains good working relations with Vietnam, the still-communist country that defeated it in the 1970s. The supplemental rationale needed to understand what seems to motivate Trump and his secretary of state, Marco Rubio, is the community of 1.6 million people in Florida who trace their ancestry to Cuba, including Rubio himself. Florida’s Cubans have long voted Republican, out of the belief that the GOP offers the clearest path to ending the Cuban system and imposing their influence on the island. As with the United States’ seemingly prospective war with Iran, it would be foolhardy, though, to assume that toppling the country’s government will be easy, and even less wise to imagine a future free of chaos if that were to happen. Unlike Iran, Cuba sits just off continental North America, within easy range even of flimsy rafts, as tens of thousands of refugees have shown during previous crises in the country. An ill-considered move to asphyxiate Havana could easily produce a new exodus, as well as prolonged domestic strife in Cuba should the regime suddenly fall. Americans, who seem strongly averse to nation-building, should be clear-eyed about the next question: Whose responsibility would it be to pick up the pieces and reconstitute an economy capable of delivering broad prosperity to Cubans? For an island that lacks Venezuela’s easily exploited resources and that lies so close to Florida’s shores, that is both a sobering prospect and one unlikely to go away.