“Rum Runner” Roy Olmstead

By Doreen Dolleman

Roy Olmstead, the famous Seattle rum runner during Prohibition was a descendant of the Connecticut Olmstead’s. He was born 18 September 1886 in Beaver City, Nebraska, the son of John Wesley Olmstead and Sarah Abby Rose. He was the fifth of six children: Florence, Frank, Ralph, Sallie, Roy and Eunice. The ancestral line of this family is: James Olmstead and Jane Bristow, Richard Olmstead and Frances Slacty, John Olmstead and Mary Benedict, Daniel Olmstead and Hannah Ketchum, Samuel Olmstead and Abiah Smith, Ebenezer Olmstead and Esther Ingersoll, Henry Olmstead and Sarah Merritt, Oliver Olmstead and Electa Hunt, John Wesley Olmstead and Sarah Rose, Roy Olmstead and (1) Viola Caliste Cotter and (2) Elise Campbell.

Roy came to Seattle in 1904. He first worked in the shipyards and then in 1907 joined the Seattle police force along with his brothers Frank and Ralph. He was a large imposing man, very intelligent, professional and rose rapidly through the ranks. He was promoted to sergeant in 1910 and lieutenant in 1917, the youngest lieutenant on the force. His WW1 draft registration states that he was tall with brown eyes and dark hair.

Washington State passed the Prohibition Initiative which made it illegal to manufacture or sell alcohol beginning on 1 January 1916. Rum running and bootlegging became a profitable enterprise that resulted in many arrests by the Seattle Police Dry Squad. Some of the Squad members were also arrested for taking bribes, stealing, and selling the confiscated alcohol. Roy Olmstead was not on the Dry Squad, but he often took part in raids. Intelligent and observant man that he was, he noted the mistakes made by the bootleggers and was intrigued by the large amounts of money to be made. He decided that it would be a profitable business if it was well organized and run professionally. He wasted no time  in setting up his business of transporting the Canadian whiskey to Puget Sound. By 1920 the National Prohibition Act had gone into affect and was much stricter than the state laws. In March of 1920 Olmstead and his bootlegging gang were caught in the Prohibition Bureau’s very first attempt to enforce the dry law in Seattle. Roy Olmstead, a police sergeant and nine bootleggers were arrested and 100 cases of whiskey confiscated. Roy was fired from the Seattle police force, fined $500 in Federal Court and was now free to devote himself full time to bootlegging!

He soon became “king” of the Puget Sound rum runners, selling the very best undiluted Canadian liquor to Seattle’s most influential residents. He chartered a fleet of boats, owned warehouses, cars and purchased a farm to stash the contraband. He delivered 200 cases daily to the Seattle area and grossed $200,000 a month. His success and lower prices put many other bootleggers out of business. He was Seattle’s largest employer! He was friends with politicians, the mayor and influential businessmen. Roy preferred to smuggle during foul weather to avoid the Coast Guard and hijackers. Although it was an extremely dangerous venture Olmstead did not allow his employees to carry firearms as he valued their lives more than the shipments of contraband. In spite of his illegal business dealings he did not drink, smoke or swear!

Roy divorced his first wife Viola on 5 August 1924 and then married Elise Campbell, a London native, whom he met in Vancouver, B.C. They settled in a mansion they called Snow White’s Palace in Seattle. In 1924 they set up Seattle’s first radio station, The American Radio and Telegraph Company (later became present day KOMO), in a spare bedroom in their home. It operated for four hours every evening, including news, weather and stock reports. Then “Aunt Vivian” (Elise Olmstead) read children’s bedtime stories which was a huge hit! All of Olmstead’s bootlegging crew listened to her program religiously. Prohibition agents believed her bedtime stories contained coded signals to the Olmstead bootleggers, but it was never proved.

The Prohibition Bureau’s plan was to bring Olmstead and his organization down. However, the rugged Washington coastline with miles of shoreline and islands made it nearly impossible to be caught. Their big break came when one of Olmstead’s lieutenant’s turned informant in exchange for a position as a Prohibition agent. Wiretapping of the Olmstead mansion also provided valuable information. The home was raided on 17 November 1924 during a party. Roy, his wife and 15 guests were arrested. In 1925 Olmstead and 89 others were indicted for violation of the Prohibition Act and conspiracy. The trial began 19 January 1926 and ended 20 February with Roy Olmstead and 20 others being convicted and the rest acquitted, including his wife. Roy was sentenced to 4 years in McNeil Federal Penitentiary and a fined $8000. He appealed to higher courts and his case Olmstead v the United States was heard in the Supreme Court in 1928. His appeal was based on the belief that evidence gathered in wiretapping was illegal. The court upheld the legality of wiretapping used in criminal investigations and Roy then served the remainder of his sentence. He was released 12 May 1931. Shortly after, in 1932 prohibition ended in Washington state and the national Prohibition Act was repealed in 1933. President Franklin D. Roosevelt pardoned Roy Olmstead in 1935 and his $8000 fine and court costs were returned.

While in prison Roy began his study of Christian Science. Upon his release he returned to Seattle and to his wife. He sold furniture and dedicated his life to being a Christian Science practitioner, visiting prisoners, counseling, leading Bible studies, teaching Sunday School and rehabilitating prisoners. He preached the evils of alcohol. Elise divorced Roy in 1943, stating that he deserted her for no cause. He remained a noteworthy citizen of Seattle until his death 30 April 1966 at 79 years of age. His obit mentioned his three daughters as Vivienne Pretzer (born 8 September 1910), Pat McFarlane and Mrs. H.W. Slocomb. In the 1920 census only daughters Vivienne (9) and Shirley (7) were enumerated.

[These to be added at a later date] The photos of Roy, his wife, mother and home are courtesy of Seattle’s Museum of History and Industry

This article first appeared in the Newsletter of the Olmste(a)d Family Association in April 2009.

The genealogical history of Roy’s family will be found at www.wikitree.com/wiki/Olmstead-4899.

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