36. Smooth Criminal: Roy Olmstead-Seattle's Good Bootlegger

🌧️🐇 Welcome back to Rainy Day Rabbit Holes! In this episode, we delve into the fascinating life of Roy Olmstead, the Gentleman Bootlegger who ruled Seattle’s underground scene during the Prohibition era. 🌆🍸 Episode Highlights: - **Woodmont Beach Arrest:** We kick off with the dramatic capture of Olmstead at his Woodmont Beach hideout. - **Seattle Origins:** Explore Roy’s early days as a dedicated police officer in Seattle and his surprising transition into the world of bootlegging. - **Bootlegging Operations:** Learn about the intricate smuggling routes from Canada and the sophisticated network Olmstead built. - **Public Persona vs. Criminal Mastermind:** Discover how Roy balanced his dual life, earning the nickname “Gentleman Bootlegger.” - **Downfall:** Follow the sequence of events that led to his ultimate arrest and the end of his empire. #### Special Mentions: - **Book Recommendation:** A huge thank you to Brad Holden for his incredible book, [Seattle Prohibition: Bootleggers, Rumrunners & Graft in the Queen City](https://bradholden.org). This episode wouldn’t have been possible without his detailed research and captivating storytelling. - **Podcast Shoutout:** Check out our friends at [Plodding Through the Presidents](https://www.ploddingthroughthepresidents.com) for more intriguing historical tales. Their deep dives into presidential history are a must-listen! - **Further Reading:** For more on Roy Olmstead’s life, visit the [Historylink.org article](https://www.historylink.org/File/289) which provides an in-depth look at his impact on the Pacific Northwest. #### Engage With Us: - **Discussion:** What surprised you the most about Roy Olmstead’s story? Do you think his charm justified his illegal activities? - **Social Media:** Follow us on @RainyDayRabbitHoles for updates, and share your thoughts using #RainyDayRabbitHoles. Thank you for joining us on this rainy day rabbit hole! Don’t forget to like, share, and subscribe for more stories that uncover the hidden corners of history. 👉 **Visit our website:** [RainyDayRabbitHoles.com](https://www.rainydayrabbitholes.com) #RainyDayRabbitHoles #Podcast #NewEpisode #RoyOlmstead #GentlemanBootlegger #ProhibitionEra #SeattleHistory #PacificNorthwest #TrueCrime

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Looking for a funny podcast that makes history wild, weird, and unforgettable?

History Unhinged: Rainy Day Rabbit Holes is the best history podcast for fans of outrageous true stories, ridiculous history, and unfiltered humor—with the occasional dip into true crime.

Hosts Shea and Jody dig up the strangest moments in American history, with a special love for the Pacific Northwest and the rest of Western North America. From haunted ghost towns and scandalous figures to bizarre disasters and a sprinkle of true crime, no rabbit hole is off-limits!

History doesn’t have to be boring—especially when it’s filled with laughter, chaos, and jaw-dropping stories they didn’t teach in school.

 

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