Roy Olmstead Biography: From Police Lieutenant to Major Bootlegger

Roy Olmstead was a major and highly successful bootlegger during National Prohibition (1920-1933). Yet he began his career in a most unusual way. Olmstead joined the Seattle, Washington, Police Department in 1907. He quickly rose through the ranks and become sergeant in 1910.

Roy Olmstead

Roy Olmstead while a police officer.

In 1916, Washington implemented state-wide alcohol prohibition. The next year Olmstead rose to the rank of lieutenant. In this role, the young police officer helped arrest many rumrunners and bootleggers. In so doing, he noticed their lack of organization and the many mistakes they made. The more strict National Prohibition went into effect in 1920. The officer realized that bootlegging could be very profitable, especially if operated in a more systematic and businesslike manner.

Olmstead the Bootlegger

So Olmstead began his own bootleg operation as a side-line. However, he lost his job after his arrest. Thus, he turned to bootlegging as a full-time and highly successful occupation.

Within a short period of time Roy Olmstead’s business became one of Puget Sound’s largest employers. He had office workers, bookkeepers, collectors, salesmen, dispatchers, and warehouse workers. And there were mechanics, drivers, rum running crews, and lawyers.

He chartered a fleet of vessels and used numerous trucks and automobiles.  He even bought a farm to cache the contraband liquor. Before long, Olmstead’s organization was delivering 200 cases of Canadian liquor to the Seattle area daily. He was grossing about $200,000 a month. That would be almost $2,500,000 in today’s dollars.

Serious Problems

But in November of 1924  police again arrested Roy Olmstead. This time it was a result of an informant and police wiretapping of his telephone. In February of the next year a court convicted convicted him for violating the National Prohibition Act (Volstead Act) and for conspiracy. As a result, Olmstead appealed his case. He argued that the  wiretapping evidence was a violation of his constitutional rights to privacy and against self-incrimination.

In 1928 the U.S. Supreme Court, in Olmstead v. the United States, upheld the conviction. Olmstead spent his four-year prison sentence at the McNeil Correctional Institute. He then became a carpenter. On December 25 of 1935, President Roosevelt gave Roy Olmstead a Christmas present by pardoned him. The President excused him from his unpaid fines and court costs ($10,300), and restored his civil rights.

Later Life

Eventually, Roy Olmstead became a full-time Christian Science practitioner. He also worked with prison inmates with an anti-alcoholism program for decades. Olmstead did this until his death in 1966 at the age of 79.

National Prohibition caused many serious problems of which widespread bootlegging was only one. Therefore, the American people rejected it three-to-one in favor of Repeal.

Roy OlmsteadProhibition was a clear failure. Yet many people and organizations today support neo-prohibition ideas. Indeed, nearly one in five adults in the U.S. today favors making drinking illegal.

References and Resources on Roy Olmstead

Broderick, H. Prohibition Seattle Style. Seattle: Dogwood, 1969.

Clark, N. The Dry Years. Prohibition & Social Change in Washington. Seattle: U Washington Press, 1965.

Economic History of Seattle.

Johnson, B. Olmstead’s Story.

Metcalfe, P. Whispering Wires. The Tragic Tale of an American Bootlegger. Portland, OR: Inkwater, 2007. (This is the best biography of Olmstead.)

Newitz, Annalee. My favorite wiretappers.

Olmstead, Roy (1886-1966) — King of King County Bootleggers. Encyclopedia of Washington State History

Olmstead v. United States: Further Readings.

Roy Olmstead: a rumrunning king on Puget Sound. Pacific Northwest Q, 1963, 54, 89-103.

Roy Olmstead: Seattle’s “Rum King.” Rainier Valley Historical Society.

Smith, Michelle. The Era of Intemperance: A Case Study of Prohibition in the Pacific Northwest