When Cuba appears in the news today, the discussion usually begins with communism, sanctions, and geopolitics. But the story really begins earlier — in the decades before the Cuban revolution.
In the 1940s and 1950s Havana was one of the most glamorous cities in the Western Hemisphere. American tourists flocked there for gambling, nightlife, music, and a kind of freedom that felt unavailable at home. Casinos, cabarets, and luxury hotels lined the waterfront. The city had the atmosphere of a tropical Las Vegas.
But beneath the glamour was a system of corruption and organised crime.
Much of the casino economy was controlled by American mob figures, particularly Meyer Lansky. Working closely with the Cuban dictator Fulgencio Batista, Lansky helped turn Havana into an offshore gambling empire. In exchange for bribes and a share of the profits, Batista granted casino licences and hotel permits to mob-backed investors.
In 1946 leading figures of American organised crime gathered at Havana’s Hotel Nacional. Among those present was Lucky Luciano. The meeting was essentially a strategic conference for the American mafia, and Cuba was central to their plans.
New luxury developments soon followed. One of the most famous was the Riviera Hotel and Casino, opened in 1957 with mob connections and huge investment. Havana’s nightlife attracted celebrities and entertainers, including Frank Sinatra, who performed in mob-connected venues and helped reinforce the glamorous image of the city.
For foreign visitors Havana looked dazzling. But the benefits were unevenly distributed. Much of the wealth generated by tourism and casinos flowed to foreign investors, criminal networks, and a small political elite. Meanwhile many ordinary Cubans lived in poverty, especially in rural areas. Corruption was widespread and political dissent was often suppressed.
To many Cubans it increasingly felt as though their country had become a playground for outsiders.
It was in this atmosphere that the revolutionary movement led by Fidel Castro gained support. Castro and his followers framed their struggle not simply as a political uprising but as a fight for sovereignty — an attempt to reclaim control of the island’s land, economy, and future.
When the revolution succeeded in 1959 the casino economy collapsed almost overnight. The mob figures fled the island, the casinos were closed, and foreign-owned assets were nationalised.
The United States responded with economic sanctions that eventually grew into the long-standing embargo that still exists today.
More than sixty years later the consequences of that conflict are still felt. Economic restrictions make it harder for Cuba to obtain medicines, spare parts, fuel, and access to international finance. Shortages and power cuts periodically shape everyday life.
As is often the case in geopolitical struggles, it is not the policymakers who carry the heaviest burden.
It is ordinary people.
There is also a striking historical irony. Much of the system that provoked the Cuban revolution — the corruption, the casino economy, the organised crime networks, and the exploitation of the island — was closely connected to American interests and American actors.
Yet the Cuban population has spent decades living under economic punishment imposed by the same country.
Recently Donald Trump predicted that Cuba’s government would “fall pretty soon” and said he would “put Marco Rubio over there.” Rubio, a Cuban-American politician from Florida who has long supported a hard line toward Havana, would presumably play a leading role in whatever Washington imagines might follow such a collapse.
Whether such rhetoric leads anywhere or not, it reveals something important. It reflects an attitude that has appeared before in history — the idea that Cuba’s future can be decided somewhere else.
And that is precisely the mindset that helped create the revolution in the first place.
History rarely repeats itself in exactly the same form. But sometimes the patterns are close enough to recognise.
For Cuba, the danger may not only lie in its past.
It may lie in the possibility that the same story is beginning again.
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