Inside Cuba

When the Mob Ruled Havana

The true story of how gangsters sliced up Cuba and created an illicit playground
By T.J. English | From Kurt Russell, July/August 2019
When the Mob Ruled Havana
Photo/AP Photo
Cool, calculating and confident Meyer Lansky ran the American mob in Cuba during the days before Fidel Castro.
In February of 1947, Frank Sinatra arrived in Havana, Cuba, holding a suitcase filled with $2 million in cash. He was flanked by two mobsters from Chicago, the Fischetti brothers, Rocco and Charlie. The brothers were cousins of Al Capone, with long-standing reputations in the businesses of illegal gambling and killing. As bodyguards they were second to none—tough, loyal and connected at the highest levels of the Mob, which, at the time, was more robust and powerful than it had been since the glory days of Prohibition. Sinatra knew all this. As a fellow traveler of the Mob since his childhood in Hoboken, where the bent-nose “cafones” and aspiring wiseguys were a vibrant …
To read the complete story, subscribe to Cigar Aficionado or purchase this issue at your local newsstand or cigar shop.

More in Inside Cuba

See all
Hefty Havanas: Cuban Cigars Are Getting Thicker...And More Popular

Hefty Havanas: Cuban Cigars Are Getting Thicker...And More Popular

Two decades ago, a Cuban cigar thicker than 50-ring-gauge was an anomaly. Today, hefty new Havanas …

Jan 17, 2019
Cuba’s Best Cigar Tobacco Farms

Cuba’s Best Cigar Tobacco Farms

Five small farms in Western Cuba grow some of the finest cigar tobacco leaves in the entire world.

Oct 26, 2018
Cuba’s Cigar Sommeliers

Cuba’s Cigar Sommeliers

These trained cigar waiters recommend a brand, cut and light your cigar, then pick the perfect …

Aug 27, 2018
Two Decades of the Habanos Festival

Two Decades of the Habanos Festival

Cigar lovers from all over the world gathered in Havana to celebrate 20 years of great smokes.

Jun 20, 2018
A Seat On Cuba’s Official Tasting Panel

A Seat On Cuba’s Official Tasting Panel

Joining Cuba’s cigar experts to evaluate blends for Havana’s future cigars.

May 1, 2018
Cuba: 25 Years Later

Cuba: 25 Years Later

A look at what has changed—and what has not—in Havana since 1992.

Dec 1, 2017