In 1960, Eisenhower signed the embargo against Cuba. Eleven presidents have come and gone since then. The Soviet Union collapsed. China became a superpower. And the embargo just kept cruising on autopilot—nobody quite remembered why, but nobody had the nerve to switch it off either. By the mid-1960s it was already obvious: the regime hadn’t fallen, but it had gained a permanent external enemy to blame for everything from bread shortages to broken-down buses. American politicians dug in anyway. That’s what happens when foreign policy gets dictated not by common sense but by resentment and domestic lobbying.
It didn’t have to go that way. Imagine Washington had chosen, back in the 1970s or 80s, not to choke the island with a blockade but to swing the doors open for business. Havana was once the tourist capital of the Caribbean—between 1915 and 1930 it drew more visitors than any other destination in the region. Hotels, restaurants, car rentals, farm exports—all of it could have flowed onto the island under an American flag. Cubans would have gotten jobs, American companies a market, and the communist leadership would have lost its favorite card: “the Yankees are to blame for everything.” But pragmatism lost, and the ritual endured.
While the U.S. locked itself out, Europeans, Canadians, and the Chinese strolled right in. They’re making money, building hotels, signing contracts. Cubans still live with shortages, listening to the bosses’ spin tales about the wicked blockade. That’s the outcome of a policy driven less by American interests than by the grievances and muscle of one particular lobby.
When the Soviet Union fell apart, Cuba was on its knees. The economy collapsed, fuel ran out, people were starving. The timing couldn’t have been better to lift sanctions, fire up normal economic relations, and let Cubans compare life before and after. The regime would have crumbled without a single shot. Instead, Little Havana and their allies in Congress dug in hard—and nothing changed. These were the same people who’d spent decades trying to kill Fidel Castro by proxy: the botched Bay of Pigs landing in ’61, the mid-air bombing of Cubana Airlines Flight 455 in ’76 (73 dead). The Church Committee archives later added poisoned food, a toxin-laced wetsuit, and an exploding cigar from the CIA’s playbook. None of it worked, but all of it pumped up the political clout of Florida’s hawks.
Now it’s 2026, and we’re watching another turn of the same spiral, just with the heat dialed up. Oil shipments blocked. Former president Raúl Castro indicted in absentia for murder. Talk of sending in troops, and not in whispers anymore. The direction comes from Secretary of State Marco Rubio, a product of that same Miami diaspora. President Trump echoes the line. On May 21 he put it bluntly: “It looks like I’ll be the one that does it”—meaning he’d be the one to “solve the Cuba problem” by force. This isn’t policy anymore. It’s a family vendetta, just funded by taxpayers.
Cuba doesn’t threaten U.S. security. No nuclear weapons, no missiles pointed at Florida. It’s a poor, exhausted island 90 miles off the American coast. What the U.S. has, by contrast, is an economy, a culture, the pull of a free market—everything needed to win without an army. A tourism boom, joint ventures, a diaspora returning with cash and connections—all of it could have worked without bombs or invasions. But instead of a calculated move, we get the same old impulse: “punish them” and “don’t give an inch.”
Stubbornness, if you stick with it long enough, starts to look like principle. In reality it’s just expensive self-deception. Sixty-six years of American policy toward Cuba prove exactly one thing: embargoes don’t topple regimes—they preserve them, and they screw over American business in the process. History won’t file this under “steadfast resolve.” It’ll file it under “how not to conduct foreign policy”—a lesson paid for by several generations of Cubans and American taxpayers alike.
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