How the Mob Secretly Ran America's Favorite Playground: Havana, Cuba

At twenty past ten on the morning of October 25, 1957, Albert Anastasia sat down in a Manhattan hotel barbershop and closed his eyes. Two gunmen walked in. Nobody was ever charged, but investigators had a theory that pointed ninety miles south of Florida, to the casinos of Havana. This video traces how the Mob came to run America's favorite playground: from Prohibition-era flights out of Key West and the opening of the Hotel Nacional, through Lucky Luciano's stay and the myth of the Havana Conference, to Meyer Lansky, Santo Trafficante and a 1955 hotel law that asked how much you would invest and never who you were. Along the way, it follows a night in Havana in 1957, with the Tropicana, the Capri, the Riviera and a Hilton paid for by a union pension fund. The story rests on three dates, each with a name attached, and an ending that involves pigs loose in a hotel lobby. It also looks at what is left of the hotels and the tourism today, and at the claim that the Mob ran Havana in secret. 0:00 The Barbershop Murder 2:05 Ninety Miles from Prohibition 6:05 The Adviser 8:15 The Law with No Background Check 10:59 Hotels Built on Other People's Money 14:25 A Night in Havana 17:27 The Bombs 20:35 The Night Batista Left 22:44 Reopened Once, Then Seized 26:38 Havana Today How the Mob Secretly Ran America's Favorite Playground: Havana, Cuba Before Cancún and Las Vegas, America had other playgrounds. Hollywood honeymooned in Acapulco. The mob ran Havana's casinos. Families filled the Catskills every summer. Then, one by one, they emptied out. America's Lost Playgrounds tells the rise and fall of the resorts, hotels, casinos and vacation towns where Americans once went to have fun — at home and just across the border. Every episode is an investigation: real dates, real names, archive photos and the story behind the decline. 🏨 Legendary hotels and resorts 🎰 Casinos and mob-era playgrounds 🌴 Hollywood's Mexico and Cuba 🎢 Forgotten beach towns and amusement parks 📅 New episodes every Tuesday and Friday Subscribe if you want to know where America used to go — and why nobody goes there anymore.