During Seattle's "dry" years of the 1920s, Roy Olmstead, through guts and guile, became the biggest bootlegger and one of the most well known personalities in Northwest history. He began as a police officer, learning the business of importing illegal liquor while making arrests. His own arrest got him fired from the police force, and he turned to bootlegging full time, eventually becoming one of the largest employers in Puget Sound, with his fleet of vessels, warehouses, accountants, salesmen, legal counsel, messengers, etc.
From Police Work to More Lucrative Work
Roy was born on September 18, 1886, in Beaver City, Nebraska, where his parents, John and Sarah Olmstead, had a farm. After coming to Seattle in 1904, he worked in the Moran Brothers Co. shipyard until he joined the Seattle Police Department on May 16, 1907. Roy Olmstead was big, had a quick intellect and a penchant for police work and rose rapidly through the ranks, being promoted to sergeant on April 5, 1910. He had two brothers on the police force, Frank and Ralph Olmstead.
On November 3, 1914, the citizens of Washington state, by a margin of 52 percent, passed State Initiative Measure No. 3, the Statewide Prohibition Initiative. This new law prohibited alcoholic beverages from being manufactured by breweries and distilleries or from being sold in bars and saloons. When the law went into effect on January 1, 1916, Washington became one of 23 states enforcing "dry laws."
The new Seattle Chief of Police, Joel Franklin "Joe" Warren (1858-1934), impressed with Sgt. Olmstead's intelligence and professionalism, appointed him acting Lieutenant in 1917, a promotion made permanent on January 22, 1919. Roy Olmstead was the youngest Lieutenant on the force and although physically imposing, was known as "the baby lieutenant."
Inevitable byproducts of prohibition were "rumrunning" and "bootlegging." For any Seattle resident wanting a quart of booze, there was always someone ready to supply it -- for a price. The local bootleggers however, were unorganized and inept, resulting in many arrests by the Seattle Police Dry Squad. Occasionally, even members of the Dry Squad were arrested for stealing and selling confiscated alcohol and for taking bribes. All of these activities were duly noted by Roy Olmstead, soon to be known in the Seattle press as "King of the Puget Sound Bootleggers."
Looking Over the Business
Lt. Olmstead, although not a member of the Dry Squad, had been involved in many raids and arrests of bootleggers. He noted their basic lack of organization and the mistakes they made. Mainly, he observed that bootleggers seemed to have a lot of money. Olmstead reasoned that an unlimited source of good liquor in British Columbia, Canada, plus an untapped market for booze in Seattle, equaled the perfect combination for a very profitable business opportunity. Bootlegging just needed someone to organize and run it like a business; Roy Olmstead was just the man for the job.
The 18th Amendment to the Constitution, imposing Prohibition nationwide, was ratified by the required 36th state on January 16, 1919, and went into effect one year later. This new federal law was much more stringent than the state laws. Now it was illegal, with a few exceptions, to import, export, manufacture, sell, buy, or transport any alcoholic beverage. The enforcement responsibility was given to the Treasury Department's newly formed Prohibition Bureau.
Roy Olmstead wasted no time becoming fully involved in bootlegging. Unfortunately, Prohibition Bureau Agents caught him in their first organized effort to enforce the "dry law" in Seattle. In the early hours of March 22, 1920, Olmstead's gang, which included Seattle Police Sgt. T. J. Clark, was unloading Canadian whiskey from a rumrunning launch at the Meadowdale dock three miles north of Edmonds. Agents had the area under surveillance and barricaded the only escape route. Olmstead managed to escape by driving his car through the bushes, around the roadblock but not before being identified by the agents.
When Agent-in-Charge Donald A. McDonald notified the Seattle Police Department of Sgt. Clark's arrest and Lt. Olmstead's escape, Olmstead was ordered to surrender to the federal authorities. The trap netted the prohibition agents two police officers, nine bootleggers, six automobiles and nearly 100 cases of Canadian whiskey. At the time, it was the largest seizure of contraband liquor on Puget Sound.
From Law Enforcement to Law Evasion
After a brief investigation by Chief Warren, Lt. Olmstead was immediately dismissed from the Seattle Police Force. He was arraigned in Federal Court, pleaded guilty to the charge and fined $500. Ironically, Olmstead could now devote all of his time and energy to his new business, bootlegging. Experience had taught him that he had to enlarge his bootlegging operation to make any significant money. This meant bigger liquor shipments, faster vessels, bigger trucks, more cars, and many more employees.
Soon Roy Olmstead's ad hoc business became one of Puget Sound's largest employers, utilizing office workers, bookkeepers, collectors, salesmen, dispatchers, warehousemen, mechanics, drivers, rumrunning crews, and legal counsel. He chartered a fleet of vessels, had numerous trucks and automobiles, and even purchased a farm to cache the contraband liquor. Before long, Roy Olmstead's organization was delivering 200 cases of Canadian liquor to the Seattle area daily, and grossing about $200,000 a month.
A Maritime Trade
The Canadian Government was charging a $20 tax per case of liquor being exported to the United States, but no tax on liquor shipments to other countries. To avoid paying this arbitrary tax, Olmstead chartered two cargo ships, loaded a few thousand cases of liquor, and manifested the cargo for Mexico. By buying from the distributors in volume and evading the Canadian export tax, he was able to sell liquor 30 percent cheaper than his competitors. Olmstead's success put many bootleggers out of business who then turned their attention to the violent occupation of hijacking liquor shipments.
After receiving their cargo in Victoria, B. C., the ships sailed northeast to small remote islands in Haro Strait where cases of liquor were off loaded and stashed. Later, the contraband liquor was retrieved by small, fast rumrunning launches and delivered to various designated spots around Puget Sound. Olmstead preferred to smuggle his liquor during foul weather when the presence of the Coast Guard and enforcement agents, as well as hijackers, was less likely. Even though rumrunning was an inherently hazardous and violent endeavor, Olmstead did not allow his employees to carry firearms. He told his men he would rather lose a shipment of liquor than a life.
The Social Whirl
By 1924, Olmstead's operation had been so successful that he now specialized in wholesaling liquor to his distributors. He had also become well known and a popular figure on the Seattle scene, rubbing elbows with the mayor and local politicians as well as important businessmen.
Roy Olmstead divorced his wife, Viola, and on August 5, 1924, married Elise Caroline Parché, also known as Campbell, a vivacious young English woman he met in Vancouver, Canada. Olmstead bought a beautiful mansion, which they dubbed the "snow-white palace," at 3757 Ridgeway Place in the exclusive Mount Baker residential neighborhood, overlooking Lake Washington and Mount Rainier.
The Olmsteads founded the American Radio Telephone Company, and had Alfred M. Hubbard, a young inventor and business partner, build a large radio transmitter and one of Seattle's first commercial broadcasting studios, Station KFQX (later KOMO), in a spare bedroom at the residence. Prohibition agents speculated Olmstead was using the station's broadcasts of children's bedtime stories to send coded messages to his rumrunning boats.
Enforcement of prohibition in the Pacific Northwest was virtually impossible. There was too much border, too much water, and too many islands and remote locations to patrol effectively -- a smuggler's paradise. Olmstead's success was common knowledge and could not be ignored. It was the job of Roy C. Lyle, Prohibition Bureau Administrator for Washington State, and William Whitney, his chief assistant and legal counsel, to bring down Olmstead's organization. Their plan was to prosecute Olmstead and his confederates for conspiracy to violate the federal prohibition laws.
Closing In On Olmstead
Lyle and Whitney's first break came in September 1924, when Al Hubbard, one of Olmstead's trusted lieutenants, decided to become an informant in exchange for a job as a prohibition agent. Hubbard was extremely knowledgeable about Olmstead's organization and the rumrunning/bootlegging business. Lyle jumped at the chance to have an undercover agent in-place next to Olmstead, with access to the intimate details of his future smuggling and bootlegging ventures.
The next break for Lyle and Whitney came in October 1924, when Canadian Customs Officials seized the Eva B, one of Olmstead's rumrunning launches, arresting three men and confiscating 784 cases of liquor. During their interrogation, the crewmembers implicated Roy Olmstead and his gang. Months earlier, wiretaps had been placed on several of the conspirator's telephones including Olmstead's home. Now, federal agents were listening intently, to all their important conversations.
Using surveillance, informants, and wiretap information, Whitney gathered enough evidence for a search warrant of Olmstead's Mt. Baker residence. On November 17, 1924, Whitney raided his home, arresting Olmstead, his wife Elise, and 15 guests and seizing all of the organization's records. Prohibition agents also raided other locations including the office of Jerry Finch, Olmstead's attorney, seizing all of their records. Lyle and Whitney were now confident there was enough evidence for a grand jury investigation. Undaunted, Olmstead continued his business as usual.
At 2:00 AM on Thanksgiving morning, November 26, 1924, federal prohibition agents arrested nine men, including Roy Olmstead, Al Hubbard, and a King County deputy sheriff. Agents seized five automobiles; a King County Sheriff's squad car; rumrunning launch No. M222, known as the Three Deuces; and 240 cases of contraband liquor at the Woodmont dock in Des Moines. Interestingly, Al Hubbard had been arrested the previous week in Snohomish County near Camano Island in connection with another liquor smuggling incident. Lyle and Whitney were certainly getting their money's worth from Hubbard.
On January 19, 1925, the Federal Grand Jury returned a two-count indictment against Roy Olmstead and 89 other defendants for violation of the National Prohibition Act and conspiracy. This proved to be the biggest trial for liquor violations in the country's history under the Eighteenth Amendment. Trial proceedings began on January 19, 1926, with 47 defendants present. Forty-three defendants either absconded to Canada before trial or became cooperating witnesses. During the trial, guilty pleas and additional dismissals by the government brought the number of defendants on trial, down to 29.
The trial ended on February 20, 1926, with the conviction of 21 defendants including Roy Olmstead and his attorney, Jerry Finch. Elise Olmstead and seven defendants were acquitted. Roy Olmstead was sentenced to four years in the McNeil Island Federal Penitentiary and fined $8,000. Jerry Finch was sentenced to two years and fined $500. Sentences for the remaining defendant ranged from 15 months to three years, with fines added. Those defendants who cooperated and testified for the government, received one-year sentences.
Roy Olmstead was in and out of McNeil Island a few times during the appeals of his conviction to higher courts. In the interim, Olmstead stood trial on his arrest at the Woodmont Dock. It was very short, beginning on November 16, 1927, and ending the following day with his acquittal. The jury didn't believe Al Hubbard's testimony and the government failed to prove that the shipment of contraband liquor belonged to Olmstead.
Olmstead's appeal was based on one argument, that evidence obtained using wiretaps was unconstitutional. At issue was the individual's right to privacy and against self-incrimination under 4th and 5th Amendments. In February 1928, U. S. Supreme Court heard the case, Olmstead v. the United States, and, in a majority decision, upheld the conviction, affirming the government's right to utilize wiretaps to gather evidence in criminal investigations. On June 28, 1928, U. S. Marshals brought Olmstead back to McNeil Island to complete his original four-year sentence.
On May 12, 1931, Roy Olmstead was released from the McNeil Island Federal Penitentiary. "He got the usual time off for good behavior, but aside from this, he served his full term plus thirty days for the $8,000 fine assessed against him," reported the Seattle Post-Intelligencer. His wife, Elise, met him at the prison's dock in Steilacoom and together, they drove back to Seattle to start a new life. Except for being immediately replaced by other bootleggers, the world of prohibition had changed little since Olmstead's incarceration. The greatest change was the advent of the Great Depression in October 1929; good times were gone forever.
In January 1932, State Initiative Measure No 61, to repeal all Washington's liquor laws, was filed in Olympia. In November 1932, Initiative No. 61 was passed by a 62 percent margin, a landslide victory. Washington's Congressional Representatives were given a clear mandate to support the repeal of the 18th Amendment and the Volstead Act (the federal legislation that enforced Prohibition). On December 6, 1932, the 21st Amendment repealing Prohibition was introduced in Congress and adopted in February 1933. The Prohibition Repeal Amendment was ratified by 36 states by December 1933 and President Franklin D. Roosevelt signed the proclamation repealing the 18th Amendment, ending 14 years of federal prohibition.
A New Direction
During his years at McNeil Island, Olmstead converted to the Christian Science faith, becoming an active practitioner dedicated to the belief that liquor is destructive to man and society. After his release from prison, Olmstead made his living selling furniture. He also spent a considerable amount of time visiting jails, working with the prisoners. On December 25, 1935, mainly due to the efforts Elise Olmstead, Franklin D. Roosevelt granted Roy Olmstead a full presidential pardon. In addition to restoring all of his constitutional rights, the pardon remitted the $8,000 fine assessed against him, in addition to $2,288 in court costs.
Elise filed for divorce on May 28, 1943 claiming Roy Olmstead "deserted her without just cause." After the divorce was granted on August 5, 1943, Elise dropped from the public eye. Olmstead stayed in Seattle, eventually becoming a full time Christian Science practitioner. He spent all of his time counseling clients, teaching the Bible, and visiting jails and prisons in the Puget Sound area, attempting to rehabilitate inmates. He operated his ministry out of a small, unobtrusive office in the Times Square Building.
Roy Olmstead remained a newsworthy personality throughout his life. His last interview was by Seattle Post-Intelligencer columnist Don Duncan, the year before Olmstead died. He was still a vibrant and active community member, teaching Sunday school and visiting the prisoners in the King County Jail every Monday morning.
Although he led an exemplary life his last 35 years, Roy Olmstead would always be known in Seattle as "King of the Puget Sound Bootleggers." He died, without fanfare, on April 30, 1966, at age 79.