Roy Olmstead (September 18, 1886 – April 30, 1966) was one of the most successful and best-known bootleggers in the Pacific Northwest region during American Prohibition. A former lieutenant in the Seattle Police Department, he began smuggling alcohol from Canada while still on the force. Following his arrest for that crime, he lost his job in law enforcement and turned to illegally importing and distributing alcohol as a full-time and highly profitable occupation. Eventually, wiretaps of his phones provided sufficient evidence for his arrest and prosecution, despite an appeal that reached the Supreme Court regarding the legality of the wiretap.