Frank Sinatra’s Mafia World Was Much CRUELER Than You Thought

On the last weekend of March 1962, President John F. Kennedy slept at Bing Crosby’s house in the California desert, while the helicopter pad Frank Sinatra had reportedly built for him in Palm Springs sat empty. America’s most famous singer had prepared for the most famous guest in the world, and the guest chose another singer’s roof. According to biographers, the reason was the company Sinatra kept, above all a Chicago crime boss named Sam Giancana. Sinatra had the voice. He had the friends. And he had an FBI file that would pass a thousand pages. So when a golden age star crossed the wrong people, who actually paid? Start in Chicago, thirty-five years earlier, with a hotel room. This documentary follows Frank Sinatra’s mafia ties, Sam Giancana and the Rat Pack, from Prohibition-era Chicago to Las Vegas and Lake Tahoe in the 1960s. It asks who really paid when Hollywood’s golden age stars got close to the mob, from Sammy Davis Jr. and Kim Novak to Peter Lawford and Marilyn Monroe.