The US Flights That Helped Fidel Castro Clear Out Dissidents - OZY | A Modern Media Company

The US Flights That Helped Fidel Castro Clear Out Dissidents

The US Flights That Helped Fidel Castro Clear Out Dissidents

By Wesley Tomaselli


Because 50 years ago, a deal between the United States and Cuba changed some families’ lives forever.

By Wesley Tomaselli

Orlando Gutierrez-Boronat tried not to squirm as he sat in a bunker in Havana’s airport in 1971, waiting to board the DC-3 that would jet him and other Cuban nationals off the island. He was tense, as they all were. Eyes darted. His mother felt scandalized because authorities had seized her wedding ring just before the flight. His father felt battered; he had done two years in a work camp before being able to request leave. Orlando and his family knew that this flight would finally mean relief from Fidel Castro’s dictatorship. They also felt like they were leaping off a cliff.

“Between 1968 and 1973, they finished wiping out whatever resistance had remained,” says Gutierrez-Boronat, who now lives in Miami. Once that plane took off, he and his family soared over the Atlantic toward Spain, free from repression — but also exiled from their home. 

The 5-year-old’s flight to Spain was part of a U.S.- and Spain-sponsored humanitarian airlift that removed Cubans from Fidel Castro’s communist grip during the late 1960s and early 1970s. Some 300,000 fled Cuba during those years and ended up in places like New Jersey, Madrid and Miami. The Freedom Flights — as they were called by their passengers — “became a vehicle of reunification” for Cuba’s exiles, explains Andy Gomez, a Cuba expert at the University of Miami. Gomez describes Fidel’s art of cleansing the island of dissidents by using American money as “masterful … when there was any kind of opposition, he would open the spigot and let the water flow.” That spigot saw half a million people trickling out of the dictatorship over the subsequent decades.

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A group of Cuban refugees in Manhattan watches President Kennedy delivering a speech on television. Kennedy described a seven-point program directed at Cuba, including a quarantine. Kennedy also warned the Soviet Union against provoking any Cuban attacks.

Source Bettmann/Getty

In 1961, the Kennedy administration botched a bid to throw out Castro and install a U.S.-friendly democracy: Washington trained Cuban exiles to invade, but when they landed in the Bay of Pigs, U.S. bombers sent to blaze the trail missed their targets — leaving the 1,400-strong group, labeled Brigade 2506, in a David vs. Goliath contest with 20,000 Cuban troops. Bogged down in bad weather, guns jammed and without reinforcements, most of the exiles wound up surrendering, and about 100 were executed. A year later, Argentine revolutionary Che Guevara saw labor communes on a tour of Maoist China and brought the idea back to Cuba, where it was used to punish and discourage dissent. The following year, under newly sworn-in President Lyndon B. Johnson, Washington made a quiet truce with Castro: The U.S. would foot the bill to peacefully fly out those who wanted to leave Cuba, and Castro would get rid of his opposition. Gutierrez-Boronat and his family were free.

Awaking to the world in a strange, new Spain, Gutierrez-Boronat remembers his mother falling over the stacks of books in Madrid’s shops. “Cuba had done away with free speech. All the newspapers, all the literature said the same thing.” Eventually, the family moved to Nicaragua and then finally settled in South Florida. “Sometimes we get lost inside the U.S.-Cuba thing — how that defines everything. People have a history of their own. It’s not just defined by how you’re related to the U.S.,” says Gutierrez-Boronat.


As people leave (or get forced out of) their homelands in greater numbers, the response to migrants and refugees is changing. Some, like Venezuelan economist Ricardo Hausmann, say immigration makes an economy more productive. U.S. President Donald Trump, Italy’s Five Star Movement and other emerging political forces around the world think otherwise — and they’re challenging the laissez-faire attitude toward the flow of people that accompanies globalization, on the shaky ground that immigration hurts more than it helps.

The U.S. often assumes itself to be a promised land for newcomers. And for some — like the victims of Ireland’s famine, Mexico’s drug war and Cuba’s dictatorship — it turned into a haven. Cities like New York, which welcomed Italian immigrants during the early 1900s, Miami with the Cubans mid-century and more recently Minneapolis with the Somali diaspora set a precedent for sanctuary cities and how to cope when people are forced into exile.

But at the same time, Gutierrez-Boronat is worried about the assumption that everyone wants to come running from their country and adopt this identity that we call “immigrant” — someone who comes to live permanently in a foreign country. The Cuban experience is a reminder that some leave their country of origin reluctantly and continue to feel like strangers in a strange land rather than cheerfully integrating into the culture of their new home. Some, like Gutierrez-Boronat, want to go back.

Now 52, tall and husky, Gutierrez thinks back to one of his most anxious memories from that day in 1971: watching a little girl getting tugged out of line by Cuban police. Her grandparents were sympathizers. Her parents wanted out. The guards took her into a separate room and pressured her to stay. But she defied them and got back in line. “There’s a lot of pain involved,” he says. “We never saw ourselves as immigrants. We saw ourselves as exiles. We never rejected the United States. But hey — we’ve been torn away from who we want to be.”

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