The great Havana building boom of 1956-1958 saw the completion of the biggest, most extravagant hotel-casinos outside of Las Vegas.  First to be erected was the glittering Hotel Capri, a modern 19-story edifice with the novelty of a rooftop swimming pool.

Hotel Capri's rooftop swimming pool

Bugsy Siegel and George Raft pal around

The Capri’s casino was fronted by the actor George Raft who had built his career playing gangsters and hanging around with them, such as Benjamin “Bugsy” Siegel.

However, the Capri’s real owner was Santo Trafficante, Jr.

Santo Trafficante waving to the press

Next to appear was Meyer Lansky’s ultra swank Hotel Riviera a 21-story, 440-room masterpiece of Miami Modern design situated directly on the Malecon facing the sea.

The last and biggest was the Habana Hilton built in Havana’s Vedado entertainment district and visible from any vantage point in the city.

The Habana Hilton dominated the surrounding area

Life Magazine’sMarch 10, 1958 issue featured the article “Mobsters Move In On Troubled Havana and Split Rich Gambling Profits with Batista.”  The piece detailed the Havana gaming scene, naming the mob’s key investors including Vegas’ Moe Dalitz and Wilbur Clark.  The impression left with readers was that a glittering new Las Vegas had suddenly arisen in the Caribbean, and was the product of mob professionalism nurtured by a corrupt government.

Life Magazines 1958 expose of the Batista-mobster marriage

Life further reported that, as a result of the casino boom, Americans were flocking as never before to the island while the average Habanero was left questioning the wisdom of the Batista-mobster marriage for Havana’s future.

By the end of 1958, the Habana Hilton and Havana Riviera were bigger than any hotel-casinos yet constructed in Las Vegas.

Habana Hilton's fabulous showroom (rendering)

In one of the grand ironies associated with the mob’s Havana investments, in April 1958, nine months before Batista fled the country, the Nevada Gaming Board declared that no holders of Nevada gaming licenses could also be investors in Cuban casinos.  The decree was a response to the opening of Havana’s big new hotel-casinos, which, along with the expansion of gambling throughout the island, was having a measurable impact on Las Vegas’ gaming receipts.  High rollers were choosing the diverse pleasures of the “Playland of the Americas” over Nevada’s remote and dusty resort.

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Also in 1958, Moe Dalitz had taken control of the Stardust Hotel, and he and his partners were still the owners of the Desert Inn.  So Dalitz had his hands full when he was forced to choose between Havana and Las Vegas that same year.

As a result, Hotel Nacional casino investors Moe Dalitz, Sam Tucker, Morris Kleinman, and Wilbur Clark, who were all deeply committed to the success of Las Vegas, opted to sell their Hotel Nacional shares (at a considerable profit) to Meyer Lansky.

The fall of Batista and the arrival of Castro spelled the end of the mob’s investments in Cuba.  On the day of Batista’s departure, the casinos were smashed and looted.

The aftermath of the people's revenge

And what became of Moe Dalitz and Wilbur Clark?  They became leading citizens of Las Vegas, the fathers of the entertainment capital of the world.

Dalitz, Elvis and Wilbur Clark

And Lansky?

Lansky walking his pooch in Miami Beach retirement