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On Thanksgiving Day, 1925, Roy Olmstead was trapped by federal prohibition agents and their Tommy guns on a lonely Puget Sound dock. His reign as the Northwest’s most prolific bootlegger had ended. But big questions—political, cultural, and legal—remained.

Why did Olmstead, the youngest lieutenant in Seattle Police Department history, form a secret gang to take over Prohibition bootlegging in the Northwest? What can we learn today from “The Good Bootlegger’s” story of whiskey-driven politics, culture wars, criminalization of popular social behavior, illegal surveillance, spies, sensational trials, and Constitution-bending trips to the Supreme Court?

Using photographs, documents, newspapers, and court cases, Steve Edmiston breathes life into Olmstead’s story by exploring historical context, his entrepreneurial brilliance, his code of conduct, and the profound impact of his legal battles today.

Steve Edmiston (he/him) is a business and entertainment lawyer with Bracepoint Law, an indie film screenwriter and producer, founder of Quadrant45, and co-founder of The Good Bootlegger’s Guild. He has keynoted for the Washington State Historical Museum, Smith Tower Rumrunner’s Club, McMenamins History Pubs, and on the Travel Channel’s Legendary Locations.

Edmiston lives in Des Moines, near the site of Olmstead’s final arrest.