The Underworld Podcast

Cuba: From Lansky’s Casinos to Castro’s Guns

October 6, 2026·59 min
Episode Description from the Publisher

Sean got beaten up in Cuba! To celebrate this, we’ve thrown together a biopoly of crime in the tropics, beginning with the story of how American organized crime flocked to Havana in the 1920s as a Prohibition rum-runner’s paradise. After World War II, mobsters then executed a takeover of Havana, building hotels, casinos, racetracks and bordellos as US tourism sought sun, sand, and vice off the Florida Strait. Chief among all Havana’s crooks were Meyer Lansky and Lucky Luciano, who in 1946 welcomed the great and good of America’s underworld to a ‘Mob Conference’ that would decide the fate of a new, offshore Mafia. But trouble was brewing—mainly in the form of a young, bearded nationalist who’d practiced his own violent form of ‘gangsterismo’ in the past. And as Havana’s criminal-friendly dictatorship buckled, the island was about to face a new anti-Mafia crusade, Fidel Castro-style. Learn more about your ad choices. Visit megaphone.fm/adchoices

Podzilla Summary coming soon

Sign up to get notified when the full AI-powered summary is ready.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.

Listen to This Episode

Get summaries like this every morning.

Free AI-powered recaps of The Underworld Podcast and your other favorite podcasts, delivered to your inbox.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.