Vice & Violence
Brothels, Bootleggers & Broken Lives
Step into the shadowy underbelly of Ottawa’s history—where the line between civic respectability and syndicate violence was razor-thin.
Long before Capone made headlines, Ottawa birthed its own mob legacy: John Patrick Looney. Born right in Ottawa’s working-class "Kerry Patch" neighborhood, Looney had a 33-year head start on Capone—building an empire of extortion, bootlegging, and prostitution along the Mississippi while maintaining a quiet double-life in Ottawa, Illinois as a devoted family man. His dual existence directly inspired the character of John Rooney (Paul Newman) in Road to Perdition.
But Looney is only the hook—local vice is the main event.
As Ottawa cracked down on illegal gambling and prostitution, vice went underground and migrated out of town. Discover the secret history of infamous hot spots like "The Elms" brothel where Bingo Smith attended St. Patricks in the morning and sold vice nightly. Follow the trail west to Naplate, where turf wars, syndicate firebombings, and gangland hits exploded across the county.
From early 1838 canal riots to mid-century brothels and mob retaliation, Vice & Violence reveals the brutal, high-stakes history hiding just beneath the surface of our quiet streets.