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
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    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
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    27 mins
  • Bootlegger Tales - Blood on the Border Line

    Bootlegger Tales - Blood on the Border Line
    Apr 15 2026
    Jack Maddox explores Vermont's brutal Prohibition-era smuggling trade, where desperate farmers risked everything running Canadian liquor across unguarded borders. The episode examines bootlegger Clarence Morse's harrowing escapes and the 1927 killing of runner Titus by federal agents, revealing how economic desperation transformed ordinary people into outlaws.

    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
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    23 mins