Seattle has its fair share of stories to add to Prohibition lore, having given rise to one of the most successful bootleggers in Pacific Northwest history – Roy Olmstead – and local filmmakers will be presenting this story in three parts at the Smith Tower beginning Monday, Feb. 11.

Presented by Steve Edmiston and Scott Schaefer (of “The Maury Island Incident“), this will be an educational and engaging speaker series told in three parts, combining history, mythology, whiskey, local references and good old-fashioned storytelling.

This series – to be held in the Smith Tower’s amazing 35th floor Observatory Bar – will explore the history of Olmstead’s rags-to-riches-to-rags story, from rising Seattle Cop to the Rumrunning King of the Northwest to inmate at McNeil Island.

Olmstead, who was busted by the Feds at the Woodmont Mosquito Fleet Dock in Des Moines on Thanksgiving Day, 1925, was said to even have a bustling “distribution warehouse” in the Sunnydale neighborhood of Burien.

The historic Smith Tower also plays a big role in this story, as it was home to Olmstead’s lawyer Jerry Finch, and Olmstead operated a remote radio station from there (his radio station became KOMO Radio).

  • Doors open at 7:30 p.m. and tickets are $20 per person.
  • Seating is limited and standing room will apply if the event is sold out.
  • A full bar and menu are available for purchase throughout the evening for your enjoyment.
  • While we encourage you to attend all sessions, it’s not required to follow along with the storyline.


Monday, February 11

Beginnings: The Seduction of a Seattle Cop

How does a rising-star cop – the youngest Lieutenant in the Seattle Police Department – decide to secretly form a gang and become enmeshed in bootlegging, only to find himself racing his car off-road to avoid capture by Federal Prohibition Agents on March 22, 1920? Join The Good Bootlegger’s Guild as we launch the story of a young man from Nebraska who joins the SPD at the tumultuous time our State goes dry – well before national prohibition – and immerse yourself in a bygone era of dramatic Seattle politics and culture wars.

Monday, March 4

The Rise of Old Roy: Seattle’s Most Original Innovator

Fired from the Seattle Police Department, Roy Olmstead makes a historic decision that will change the business and political landscape in the Northwest throughout the 1920s: with his “free time,” he will go into bootlegging booze full time. What makes Olmstead different from every other bootlegger in Seattle, the Northwest, and the entire nation is a surprisingly classic tale of Northwest entrepreneurship, innovation, and spirit.

Monday, April 1

The Hard Fall: The Feds Fight Back

Olmstead’s good guy anti-hero popularity peaks, with his remarkable popularity driven by better whiskey, lower prices, and an ethical commitment to non-violence. Olmstead is labeled in the media as “The Good Bootlegger,” but it’s too good to last. While Olmstead is beloved by many as the opposite of a Capone-style, violence-driven whiskey operation, his success attracts the country’s most innovative federal prohibition agents to Seattle who determines – using new technology – to bring the Olmstead empire crashing down.

Buy tickets online here

This plaque – installed in 2017 in the Woodmont neighborhood of Des Moines – commemorates where Roy Olmstead was busted by the Feds on Thanksgiving Day, 1925. The piling on the right in the background – nicknamed “Ol’ Roy” – is all the remains from a Mosquito Fleet dock that Olmstead used on his late night rumrunning sessions. Photo by Melody Edmiston.

Scott Schaefer

Founder/Publisher/Editor. Three-time National Emmy Award winning Writer (“Bill Nye the Science Guy”), Director, Producer, Journalist and more...