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.