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Roy Olmstead

Roy Olmstead
Born (1886-09-18)September 18, 1886
Beaver City, Nebraska
Died April 30, 1966(1966-04-30) (aged 79)
Seattle, Washington
Nationality American
Occupation Policeman, then bootlegger
Criminal charge Violating the National Prohibition Act and for conspiracy
Criminal penalty
Criminal status Served term, later Pardoned
Allegiance King County Bootleggers
Conviction(s) January 19, 1925 (age 38)

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 to bootleg part-time 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 from Canada 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.

Born in 1886 to farmers John and Sarah Olmstead, in Beaver City, Nebraska, Roy moved to Seattle, Washington, in 1904. Working in the Moran Brothers Co. shipyard before joining the Seattle Police Department on May 16, 1907, he rose rapidly through the ranks and was promoted to sergeant on April 5, 1910; his brothers Frank and Ralph were also on the Seattle force. Seattle police chief Joe Warren (1858–1934) was so impressed with Sgt Olmstead's intelligence and professionalism, he appointed him Acting Lieutenant in 1917, with the promotion being made permanent on January 22, 1919.

When Washington State prohibited the manufacturing and selling of alcohol in 1916, the police force began raiding bootleg operations. Olmstead, noting the potential for profit, began his own bootlegging operation while still a policeman. On March 22, 1920, Olmstead was identified driving around a roadblock set by Prohibition Bureau agents raiding a rum-running operation. He was fired from the force and paid a fine of $500, but now could devote his full attention to his smuggling operations.

He ran his illegal operation like a business and before long he became one of the largest employers in Puget Sound. Known on the West Coast as "the Good Bootlegger", Olmstead did not engage in the practice of diluting his contraband with toxic industrial grade chemicals in order to increase his profits, selling only bonded liquor imported from Canada. To most other bootleggers, smuggling alcohol was but one facet of their criminal organization, and many were involved in prostitution, gambling, gun-running, and narcotics trafficking. Olmstead did not engage in these activities, and many did not regard him as a "true criminal" as a result. Despite the risks involved in rum-running, Olmstead did not allow his employees to carry firearms, telling his men he would rather lose a shipment of liquor than a life.


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