Bootlegger Tales cover art

Bootlegger Tales

Bootlegger Tales

Written by: Inception Point AI
Listen for free

About this listen

 Host Jack Maddox uncovers dangerous true stories of Prohibition-era bootleggers smuggling liquor by land, sea, and air. From rum runners gunned down by federal agents to ex-cops running smuggling empires and daredevil pilots flying whiskey for Al Capone, these tales reveal desperate men who built fortunes outside the law.

For more content like this, visit QuietPlease.aiCopyright 2026, Inception Point, AI Inc. True Crime World
Episodes
  • Bootlegger Tales - Whiskey in the Clouds

    Bootlegger Tales - Whiskey in the Clouds
    Apr 15 2026
    Join AI host Jack Maddox as he uncovers Prohibition's forgotten chapter: daredevil pilots smuggling whiskey by air. From Richard Halliburton's $13,000 fine to Al Capone's aerial fleet, discover how bootleggers turned America's skies into smuggling corridors and one pilot's ultimate price.

    Loved this episode? Discover more original shows from the Quiet Please Network at QuietPlease.ai, explore our curated favorites here amzn.to/42YoQGI, and catch just a slice of our AI hosts in action on Instagram at instagram.com/claredelish and YouTube at youtube.com/@DIYHOMEGARDENTV

    This content was created in partnership and with the help of Artificial Intelligence AI
    Show More Show Less
    27 mins
  • Bootlegger Tales - Rum, Ruin & Rum Row

    Bootlegger Tales - Rum, Ruin & Rum Row
    Apr 15 2026
    Jack Maddox explores how Prohibition created two bootlegging empires with opposite philosophies: Seattle's Roy Olmstead, the "Good Bootlegger" who ran his operation like a legitimate business without violence, and Rhode Island's Carl Rettich, whose reign included murder and terror. One ended pardoned and reformed; the other, imprisoned on Alcatraz.

    Loved this episode? Discover more original shows from the Quiet Please Network at QuietPlease.ai, explore our curated favorites here amzn.to/42YoQGI, and catch just a slice of our AI hosts in action on Instagram at instagram.com/claredelish and YouTube at youtube.com/@DIYHOMEGARDENTV

    This content was created in partnership and with the help of Artificial Intelligence AI
    Show More Show Less
    27 mins
No reviews yet