Born in 1886 on a Nebraska farm, Roy Olmstead’s journey from a law-abiding police officer to one of Seattle’s most notorious bootleggers is a story rich with contradiction, innovation, and the law’s evolving landscape during Prohibition.

Olmstead moved to Seattle just after the turn of the 20th century, working first in Moran Bros. shipyards before joining the Seattle Police Department alongside his brothers, Frank and Ralph. Over the years, Roy worked his way up to Lieutenant. However, his life took a sharp turn in 1916, when Washington State banned alcohol. Seeing a profitable opportunity, Olmstead launched a bootlegging operation while still serving as a police officer. His profitable scheme unraveled in 1920 when he was caught in a sting operation, fired, and fined $500 for his illicit activities. Instead of retreating, Olmstead turned to full-time bootlegging, establishing one of the largest smuggling operations in the Pacific Northwest.

Roy’s operation relied heavily on liquor sourced from Vancouver, British Columbia, where Canadian Prohibition laws didn’t apply. His vessel, the Eva B, routinely transported shipments to D’Arcy Island, near the U.S.-Canada border. Unlike the violent and seedy operations of many gangsters of the era, Olmstead’s business was run with precision and professionalism. He never diluted his whiskey or resorted to violence, nor did he engage in other illegal activities like gambling, narcotics, or prostitution.

In 1924, following the dissolution of his first marriage, Olmstead married Elise (known as “Elsie”), a Vancouver native he met while on a booze run. That same year, the couple launched a groundbreaking new venture—a radio station, KFQX, with the help of inventor Al Hubbard. Though the station’s license listed Hubbard as the owner, it was largely Elsie’s brainchild, and she handled most of its operations, from programming to finances. Broadcasting from their mansion in Seattle’s Mt. Baker neighborhood, KFQX became one of the most powerful stations in the U.S., running 1,000 watts.

Elsie Olmstead, who hosted a children’s bedtime stories program as “Aunt Vivien,” was rumored to weave coded messages into her stories to signal Roy’s offshore booze ships. Whether true or not, KFQX became a profitable station, attracting sponsors like Buescher musical instruments and Pacific Music Co., paying $80 an hour for airtime. The Olmsteads built KFQX into a legitimate enterprise, but Roy’s underground activities remained under federal scrutiny.

In late 1924, federal agents conducted a raid on the Olmsteads’ mansion while Elsie was on-air. Roy, Hubbard, and several others, including the bandleader Earl Gray, were arrested. Though Olmstead and his associates were charged, agents found no incriminating evidence in the home itself. The government, however, had wiretapped Roy’s telephone—a fact that would become central in his trial.

In January 1925, a federal grand jury indicted Olmstead and 89 others for conspiracy to violate the National Prohibition Act. The trial concluded in February 1926, with Olmstead sentenced to four years of hard labor and fined $8,000. He appealed the decision, arguing that the wiretap evidence had been obtained without a warrant, violating his constitutional rights. The case, Olmstead v. United States, went to the Supreme Court, which upheld his conviction in 1928. Roy served his sentence at McNeil Island Correctional Institute but was released early in 1931 for good behavior, returning to his Seattle home to be with his wife & daughter, obtaining employment as an insecticide salesman & fumigator. The opulent mansion in the Mt Baker neighborhood had been sold to pay off legal costs & other debts. The Olmsteads now resided in an apartment at 1220 Boren Avenue in Seattle. The Olmsteads had leased KFQX to advertising executive Birt Fisher to pay for Roy’s mounting legal fees. Fisher renamed the station KTCL, but he struggled to keep it afloat. After Roy’s conviction, the station equipment was sold to Vincent Kraft, who used it to establish 570 KXA, marking the end of KFQX under the Olmstead name.

After his release, Roy began a quiet, On 25 December 1935, President Franklin D. Roosevelt granted him a full presidential pardon. Besides restoring his constitutional rights, the pardon remitted $100,000 the IRS claimed he owed in unpaid liquor taxes. Olmstead also had his unpaid $8,000 fine & court costs forgiven as part of the deal. After receiving his pardon, he next took up employment as a Credit Bureau executive.By the time Roy Olmstead was released from prison, Prohibition was in its final years. In a twist of fate, the man who had made a fortune from smuggling alcohol would later renounce the trade. During his time in prison, Roy became a devout Christian Scientist. Upon his release,  he turned to a quiet life, but active community life, teaching Sunday School, and making regular visits to McNeill Island & other regional prisons offering counselling to those incarcerated. The U.S. repealed Prohibition in 1933. In 1935, President Franklin D. Roosevelt granted him a full pardon, restoring his constitutional rights and forgiving his unpaid liquor taxes and fines. Roy and Elsie Olmstead’s marriage ended in 1943, after citing personal and religious differences. Roy continued his quiet, reformed life, working as a credit bureau executive until his death on April 30, 1966, at the age of 79. His legacy, however, endures in Seattle’s rich history of both crime and radio broadcasting. Though their opulent mansion in Mt. Baker was sold to pay off debts, the house still stands as a monument to one of Seattle’s most colorful and complex figures.