Today in history: 'King of Puget Sound Bootleggers' arrested

"During Seattle's prohibition years in the 1920's, Roy Olmstead became one of the largest and most successful bootleggers in King County. Learning how the trade operated from involvement in raids and arrests while serving as a Seattle Police Lieutenant, Olmstead noted the lack of organization of many bootleggers and began his own operation. His operation eventually grew to include many vessels, trucks, warehouses, and employees importing liquor from Canada. In 1924 Olmstead married his second wife, Elise, from England and they established the American Radio Telephone Company which they operated from their Mount Baker home. It was suspected that the children's bedtime hour was used to relay coded messages to the various rumrunners employed. Suspicious of the activities, federal agents employed surveillance techniques and wiretapping to arrest Olmstead, his wife, and nine other men in 1924. After a Federal Grand Jury indictment in 1925, he appealed in a landmark case on the grounds that wiretapping was unconstitutional based on the 4th and 5th Amendments. Elise was acquitted, however, Olmstead was convicted, served four years time at McNeil Island Penitentiary and was released in 1931. Having converted to the Christian Science faith in prison, and now believing that alcohol was destructive, Olmstead spent his remaining years counseling and teaching from the Bible, providing rehabilitative services to Puget Sound inmates, and operating a ministry from the Times Square Building. Elise divorced him in 1943 claiming desertion. He continued his community service activities until his death in 1966. He is shown here with his wife Elise in 1925." -MOHAI. Photo courtesy MOHAI, Seattle P-I Collection, image number 1986.5G.2261.1.
Courtesy MOHAI

"Elise Olmstead, originally from England, was the second wife of Roy Olmstead, one of the largest and most successful bootleggers in King County during the 1920s Prohibition years. Learning how the trade operated from involvement in raids and arrests while serving as a Seattle Police Lieutenant, Olmstead began his own operation. After an arrest and dismissal from the Seattle Police Force, he was able to devote all his time to his operations which eventually grew to include many vessels, trucks, warehouses, and employees importing liquor from Canada. Elise and Roy established the American Radio Telephone Company which they operated from their home in Seattle's Mount Baker neighborhood. It was suspected that the children's bedtime hour was used to relay coded messages to the various rumrunners employed. Suspicious of the activities, federal agents employed surveillance techniques and wiretapping to arrest Elise, Roy, and nine other men in 1924. After an initial Federal Grand Jury indictment in 1925, the 1926 trial proceedings at the time of this photograph were the largest in the country's history of liquor violations starting out with 47 defendants. Elise was acquitted, however, Olmstead was convicted and sentenced to four years in prison and fined $8,000. After losing his appeal, Olmstead served his time at McNeil Island Penitentiary and was released in 1932. Having converted to the Christian Science faith in prison, and now believing that alcohol was destructive, Olmstead spent his remaining years counseling and teaching from the Bible, providing rehabilitative services to Puget Sound inmates, and operating a ministry from the Times Square Building until his death in 1966. Elise divorced Olmstead on the grounds of desertion without cause in 1943. She is shown here circa 1926." -MOHAI. Photo courtesy MOHAI, Seattle P-I Collection, image number 1986.5G.2278.
Courtesy MOHAI

Learning how the trade operated from involvement in raids and arrests while serving as a Seattle Police Lieutenant, Olmstead noted the lack of organization of many bootleggers and began his own operation. After an arrest and dismissal from the Seattle Police Force, he continued his operations which eventually grew to include many vessels, trucks, warehouses, and employees importing liquor from Canada. Along with his second wife, Elise, Olmstead established the American Radio Telephone Company which they operated from this home in Seattle's Mount Baker neighborhood. It was suspected that the children's bedtime hour was used to relay coded messages to the various rumrunners employed. Pictured: Olmstead residence, Seattle, ca. 1925 — Learning how the trade operated from involvement in raids and arrests while serving as a Seattle Police Lieutenant, Olmstead noted the lack of organization of many bootleggers and began his own operation. After an arrest and dismissal from the Seattle Police Force, he continued his operations which eventually grew to include many vessels, trucks, warehouses, and employees importing liquor from Canada. Along with his second wife, Elise, Olmstead established the American Radio Telephone Company which they operated from this home in Seattle's Mount Baker neighborhood. It was suspected that the children's bedtime hour was used to relay coded messages to the various rumrunners employed.

Pictured: Olmstead residence, Seattle, ca. 1925
P-I File

After an initial Federal Grand Jury indictment in 1925, the 1926 trial proceedings as shown in this photograph were the largest in the country's history of liquor violations starting out with 47 defendants. Olmstead was convicted and sentenced to four years in prison and fined $8,000. His wife was acquitted. He appealed in a 1928 landmark case on the grounds that wiretapping was unconstitutional based on the 4th and 5th Amendments. After losing his appeal, Olmstead served his time at McNeil Island Penitentiary and was released in 1931 . Having converted to the Christian Science faith in prison, and now believing that alcohol was destructive, Olmstead spent his remaining years counseling and teaching from the Bible, providing rehabilitative services to Puget Sound inmates, and operating a ministry from the Times Square Building until his death in 1966. Elise divorced him in 1943 on the grounds of desertion. Pictured: Federal grand jury in Roy Olmstead bootlegging case, Seattle, 1926 — After an initial Federal Grand Jury indictment in 1925, the 1926 trial proceedings as shown in this photograph were the largest in the country's history of liquor violations starting out with 47 defendants. Olmstead was convicted and sentenced to four years in prison and fined $8,000. His wife was acquitted. He appealed in a 1928 landmark case on the grounds that wiretapping was unconstitutional based on the 4th and 5th Amendments. After losing his appeal, Olmstead served his time at McNeil Island Penitentiary and was released in 1931 .

Having converted to the Christian Science faith in prison, and now believing that alcohol was destructive, Olmstead spent his remaining years counseling and teaching from the Bible, providing rehabilitative services to Puget Sound inmates, and operating a ministry from the Times Square Building until his death in 1966. Elise divorced him in 1943 on the grounds of desertion.

Pictured: Federal grand jury in Roy Olmstead bootlegging case, Seattle, 1926
P-I File

Pictured here: Roy and Elise Olmstead with Roy's mother Sarah at courthouse, Seattle, 1926 (during Olmstead's trial). The 1926 trial proceedings at the time of this photograph were the largest in the country's history of liquor violations starting out with 47 defendants. In this photograph, Olmstead is shown on the steps of the courthouse with his mother and wife Elise who was acquitted in the trial.
P-I File

It's a tale as old as mistrust in authority figures: Hotshot cop with a quick intellect shoots through the ranks, becoming a sergeant within three years and the youngest lieutenant on the force.

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He's got a knack for police work and though he's not physically imposing (earning the nickname "the baby lieutenant"), he impresses superiors with his professionalism and intelligence. He dutifully participated in busts and raids of rum-smugglers, and noted when members of the "Dry Squad" were arrested for stealing from the confiscated goods or taking bribes.

And he was running the biggest bootlegging operation in the Pacific Northwest.

Roy Olmstead went from rising star to "King of the Puget Sound Bootleggers," helping to smuggle alcohol during the Prohibition period in the early 20th century. And he was able to build up an empire thanks to the inside track he had of observing how both sides of the law operated.

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And it worked for a while – until he got caught, 96 years ago today.

Olmstead, who was born in Nebraska, moved to Seattle in 1904 and became a police officer in 1907. It would take him ten years to become an acting lieutenant, with Washington residents having already voted to become a "dry state" by that point, with a margin of 52 percent. By 1919, when the 18th Amendment of the Constitution imposed Prohibition nationwide, he was a full lieutenant.

And having observed how the booze market was being underserved by well-funded but disorganized bootleggers (with an emphasis on the well-funded), with a whole bunch of quality liquor right across the border in Canada, Olmstead figured he could be the businessman for the job.

That is, until March 22, 1920. Two months after Prohibition went into effect, Olmstead's operation was caught in a bust. Though Olmstead was in the car that managed to evade the road blockades, he was spotted and recognized by the agents.

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The young hot shot was promptly fired, arraigned in federal court (where he pled guilty), and fined $500. After that he was free to go ... build up his bootlegging empire full time.

Which is exactly what he did: His business soon became one of the largest employers in the region, according to HistoryLink. His crew of "office workers, bookkeepers, collectors, salesmen, dispatchers, warehousemen, mechanics, drivers, rumrunning crews, and legal counsel" would deliver about 200 cases of Canadian liquor to the Seattle area daily, grossing about $200,000 a month (something close to $3 million in today's money).

Olmstead commanded a chartered fleet of vessels, trucks and automobiles to run the booze, and he even "purchased a farm to cache the contraband liquor." In true Seattle fashion he preferred doing his work in terrible weather (to avoid Coast Guard interference). His cargo ships would bear a manifest for Mexico, to avoid the $20 tax per case of liquor being shipped to the U.S. – which helped him undercut competitors by 30 percent.

He wouldn't allow his team to carry firearms, and told his men he would rather lose a shipment than a life. Coupled with his inclination for bribery rather than violence, he earned the nickname as "The Good Bootlegger," and rubbed elbows with plenty of Seattle elite. He bought local officials "wholesale," as Ken Burns' documentary on Olmstead puts it; it made his whole operation an open secret among everyone on his payroll.

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Which would only help his empire grow more powerful: His second-wife Elise would read children's bedtime stories on their radio station (which they operated out of their house), in which the Olmsteads would code messages to the rumrunning boats.

Bootlegger Roy Olmstead, 1920s: A former Seattle cop who left the force to become king of the local rum-runners during Prohibition, Roy Olmstead built Seattle’s first radio station in his Mount Baker home. Many of the listeners were his accomplices waiting for code words in the broadcasts. Few citizens thought of Olmstead as a criminal, though he was arrested in 1926 and served 35 months in a federal prison.Seattle Post-Intelligencer

He would eventually get caught in 1924 by the Prohibition Bureau in Washington, thanks to surveillance, informants and wiretap information. By January 1925, the Federal Grand Jury had returned a two-count indictment against Olmstead and 89 other defendants.

The "biggest trial for liquor violations" in country's history wouldn't end until February 20, 1926, with the conviction of 21 defendants, including Olmstead and his attorney. The former-baby lieutenant would be fined $8,000 and sentenced to four years, and though he tried to overturn it on a wiretap technicality (a case which traveled all the way to the Supreme Court) he would serve his full term.

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After losing his appeal, Olmstead served his time at McNeil Island Penitentiary and was released May 11, 1931. This photograph of Olmstead leaving the prison launch was taken on the day of his release when he arrived at Steilacoom landing. Having converted to the Christian Science faith in prison, and now believing that alcohol was destructive, Olmstead spent his remaining years counseling and teaching from the Bible, providing rehabilitative services to Puget Sound inmates, and ope — After losing his appeal, Olmstead served his time at McNeil Island Penitentiary and was released May 11, 1931. This photograph of Olmstead leaving the prison launch was taken on the day of his release when he arrived at Steilacoom landing.

Having converted to the Christian Science faith in prison, and now believing that alcohol was destructive, Olmstead spent his remaining years counseling and teaching from the Bible, providing rehabilitative services to Puget Sound inmates, and ope
P-I File

A year and a half later Prohibition in Washington state was repealed. The country would follow suit a month after that.

Olmstead would stay in Seattle, becoming a Christian Science practitioner after converting in prison. He received a full presidential pardon from Franklin D. Roosevelt in 1935, thanks to the efforts of Elise (who would later divorce Roy). He died at age 79, after 35 years on the straight and narrow, as an active member of the Seattle community member.