The Rise and Fall of Chicago's Most Corrupt Mob Neighborhood: Taylor Street

On Taylor Street, bootleggers built fortunes—and some of the police paid to stop them came to collect a cut. In the heart of Chicago’s Little Italy, the Genna brothers turned Prohibition into a lucrative criminal enterprise. Illegal alcohol flowed from neighborhood stills, money bought protection, and violent rivalries made fortunes dangerously short-lived. Police payoffs helped keep the business running, exposing how deeply corruption had entered the institutions meant to enforce the law. This documentary explores the rise and fall of Taylor Street’s criminal world: the bootlegging operations, neighborhood power brokers, and connections between organized crime and Chicago’s political machine. As the underworld evolved, Taylor Street became the base of one of the Chicago Outfit’s original street crews—a place whose influence extended far beyond its own blocks. How did a neighborhood become such fertile ground for criminal power? And what allowed that power to survive across generations? Alongside this history lived families building businesses, raising children, and holding their community together. When urban renewal arrived, many faced a different struggle. Homes and shops were marked for demolition to make way for the University of Illinois campus. Residents organized, protested, and fought to preserve the neighborhood they knew, but much of that world was swept away. From illicit fortunes to demolished blocks, discover how crime, political influence, and redevelopment shaped Taylor Street—and the human cost behind its notorious reputation. Subscribe for more documentaries exploring Chicago’s criminal empires, forgotten neighborhoods, and the struggles over who controls the city. #ChicagoHistory #TaylorStreet #ChicagoOutfit #OrganizedCrime #LittleItaly