Ep 3.25: Gangs, Bootleggers, and a Priest in the Crossfire: St. Louis Under Prohibition

In this episode, Monsignor and Teresa continue their deep dive into the turbulent 1920s, turning their focus to the rise of St. Louis gang culture during Prohibition. Monsignor traces the intertwined stories of Tom Egan, Snake Kenny, and the rival Hogan and Egan gangs—men whose lives moved between politics, saloons, and violent street power. Alongside these underworld battles, he highlights the remarkable pastoral presence of Father Timothy Dempsey, who ministered to dying gang leaders, negotiated temporary truces, and tried to pull young men away from the cycle of revenge. The episode also explores the spread of smaller neighborhood gangs, the terror inflicted on immigrant communities, and the eventual collapse of Prohibition’s “noble experiment.” Through vivid stories and thoughtful reflection, Monsignor reveals how crime, corruption, and Catholic compassion collided in a decade that reshaped the city’s moral landscape.