Until 1959, when Fidel Castro toppled the Fulgencio Batista oligarchy, Cuba was America’s Caribbean playground of choice and Key West’s next-door neighbor where we went to shop, visit family and perhaps schedule a doctor visit. Havana was the big city, flush with goods and services not found in tiny Key West. In 1953, Havana’s population was 1.3 million, Key West’s but 21,000.
Batista brought that prosperity, and the U.S. government loved Batista. During his first term, from 1933 to 1944, Batista consolidated his power among like-minded oligarchs, courted labor unions and government workers and delivered an economy flush with education, healthcare, budding tourism and public works.
A bloodless military coup in 1952 returned Batista to power, and from then until 1959 he delivered a reign of political terror, obscene embezzlement of public funds and overt corruption. But the U.S. government loved him, turning a blind eye to Batista’s dictatorship and touting instead his anti-Communist credentials.
Then came Castro. In 1960 Castro nationalized foreign assets, hiked taxes on imports and morphed his socialism into a decades-long alignment with the Communist Soviet Union.
The U.S. government was having none of that. Virulently awash in anti-Communist rhetoric and policy, first the Eisenhower administration and then the Kennedy administration cut Cuba loose, closed borders, failed to overthrow the Castro government and turned our attention to Communists in Vietnam.
On Dec. 26, 1991, the Soviet Union fell, and with that Cuba began what became a grueling descent into grinding poverty and political impotence for all but the most privileged. Propped up until last week by its alliance with Venezuela, Cuba faces a bleak prospects.
Can we allow Cuba to fall?
Closer to Havana than to Miami, Key West has a Cuban heritage tightly woven into our island’s life, food, language, music, art, family ties and culture. It’s impossible to know where one begins and the other ends. Key West Cubans represent generations of U.S. citizens who retain strong ties to and financial support for family members who’ve remained in Cuba.
There was a time in the 1880s, at the height of the cigarmaking industry, when a third of Key West’s population was born in Cuba. Though Cuban immigration has slowed to a trickle and generations of Cubans have assimilated into “American” culture, about 23 percent of our island’s population is of Cuban descent.
On Saturday morning, Jan. 3, President Donald Trump announced he’d launched a military strike into Venezuela, capturing its dictator President Nicolás Maduro and his wife and partner, Cilia Flores. Just before noon Trump said, “We are going to run the country until such time that we can do a safe, proper and judicious transition.”
Given the economic dependency between Cuba and Venezuela, Trump’s longstanding personal lust for developing in Cuba and his administration’s appetite for Western Hemisphere dominance, my question seemed logical: Will Cuba be next?
Like clockwork he answered on Sunday: “Cuba is ready to fall.”
The prospect of the United States taking over Cuba isn’t particularly reassuring. We’ve not had the best track record for running U.S. territories. Since World War II, we’ve turned nation-building failures into wars in Vietnam, Iran, Iraq, Afghanistan and parts of Africa.
Cuba’s own precarious political history doesn’t lend itself to a stable foundation to be run by U.S. interests, though surely we can hear the glee in corporate boardrooms as they anticipate explosive tourism potential with perhaps a heaping side dish of sugar from fallow cane fields. When Americans last “ran” Cuba, organized crime and the sugar cartels ruled the island as a fiefdom for the rich and powerful, the “Epstein class,” if you will.
And yet, Trump is right. Cuba is ready to fall. Medical care is limited. Food, shelter and electricity are rationed to the point of despair. Despite almost heroic preparation in eastern Cuba before Hurricane Melissa, the October 2025 Cat 3 storm, recovery is painfully slow. With the removal of Venezuelan oil and financial support, Cuba stands to unravel.
For many in Key West that means increasing hardships and uncertainties for their families and friends only 90 miles away.
There’s no easy choice here. Politically and ideologically I am appalled at the administration’s determination to rule the Western Hemisphere and its hunger for Greenland, Mexico and Canada. But Cuba is Key West family. How can we in good conscience allow it to fall further?
Helping Venezuela rebuild and keeping Cuba from worse failure will be a tall order, and Trump’s administration hardly seems equal to it.
It has traded our international diplomatic toolbox for a military hammer. It has replaced skilled diplomats with ideologs. It has gutted international programs for buttressing democracy and providing humanitarian and medical assistance in favor of plundering resources. Cultural exchanges, where people discover their fundamental similarities, have given way to “America first” chest-thumping, insults to allies, Orwellian visa restrictions and travel bans.
How the administration proceeds WITH Venezuela, not IN it as overlords or exploiters, will be a crucial indicator of what might be ahead for Cuba. If Trump continues to focus more on oil resources than working to re-establish a truly democratic society, things look grim.
Learn more
https://www.wlrn.org/culture/2015-01-07/when-key-west-was-cuban
https://www.loc.gov/classroom-materials/immigration/puerto-rican-cuban/crossing-the-straits
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