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How the Mob Lost Havana and Decided Castro Had to Go

Its casinos, drugs, and women made Cuba a second Vegas, until the 1959 takeover shut the business down.

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Who Killed JFK? · Strange Bedfellows

Havana was once a second Las Vegas for the American mob, and then it was gone.

Before 1959, organized crime leaders Carlos Marcello, the New Orleans boss, and Santo Trafficante, his partner tied to Tampa, ran the island's casinos, drugs, and trade in women. The setup worked like the gambling business in Las Vegas, Nevada, with steady income from betting and vice.

To them the island worked like an offshore Las Vegas. No reliable total for the earnings was ever fixed, yet the trade was described as enormous and still growing, so what they had already built promised to become worth even more.

Then Cuban leader Fidel Castro took power in 1959 and expelled the crime syndicates from the capital. He closed their casinos and drug operations and cut them off from the island. Marcello and Trafficante lost their casinos and drug business there.

For the mob, business came first, not personal grudges. The mob also disliked Attorney General Robert Kennedy, who crime leaders believed was pursuing them, but the Havana seizure was about money. It gave them a financial reason to want Castro gone.

Their goal became getting rid of Castro. That shared aim made the Mafia and the Central Intelligence Agency, the American spy service, strange bedfellows in the campaign against the Cuban government.

Questions people ask

Who were Marcello and Trafficante?

Carlos Marcello led the New Orleans crime family, and Santo Trafficante Jr. led the Tampa family with deep interests in Florida and Cuba. Both invested heavily in Havana gambling and hotels during the 1950s, when American tourists flocked to the island.

What happened to Havana's casinos after 1959?

Castro's government closed casinos soon after taking power, briefly allowed some to reopen, then shut them down and seized hotels and other properties in the early 1960s. Havana never returned as a gambling resort, and Las Vegas grew instead as America's gambling capital.

Did the mob ever get back into Cuba?

No. The United States broke relations with Cuba, imposed an embargo, and travel was sharply restricted for decades. Without access to the island, American crime groups focused on Las Vegas, the Bahamas, Atlantic City, and other legal or tolerated markets.