When Bootleggers and Cops Fought Over Seattle’s Liquor Trade


Editor’s Note: This piece was first published at Brad Holden’s “Vice Files” Substack page. Brad is a Seattle writer and historian, the author of Seattle Prohibition: Bootleggers, Rumrunners and Graft in the Queen City, among other volumes exploring Seattle’s history. He is also part of the Dim Lights & Stiff Drinks podcast, which explores dive bars in Seattle.

When it comes to Prohibition-era Seattle, the historical figure that people are most familiar with is Roy Olmstead; he ran the city’s largest booze operation during the 1920s, earning himself the title as “King of the Puget Sound Bootleggers.” Prior to Olmstead, though, there existed an earlier wave of bootleggers – composed of two rival gangs — who battled it out over control of the local liquor trade. While Olmstead’s story has reached almost mythological heights, this first generation has been surprisingly overlooked. This is especially puzzling given that the thuggish exploits of these early booze rackets provided for some rather sensational newspaper headlines and were in stark contrast to Olmstead’s more genteel style of operations. 

The first Seattle liquor syndicate to emerge was headed by Edward Jack Margett, a military vet who would later be referred to as “Pirate Jack.” Very little is known about Margett’s early life other than he enlisted in the U.S. Army sometime in the early 1900s. He was assigned to the Army’s cavalry division and, despite only being in his late teens, he quickly became known for his horse-riding abilities. One account reported that he was “one of the most daring and spectacular riders in the entire army.”

Due to his impressive equestrian skills, he began competing in various horse races as a representative of the U.S. Army, eventually being dispatched to the horse racing circuit in Washington state. It was during one such race at the Meadows racetrack that Margett discovered Seattle and decided to make the city his home. After his military enlistment ended in 1908, Margett worked for a little over a year as a streetcar conductor before making a career switch to law enforcement. 

It was in the spring of 1910 that Margett was hired on as an entry-level patrolman with the Seattle Police Department. The police chief at the time was Charles “Wappy” Wappenstein, a colorful character who would later serve time at the Walla Walla State Penitentiary. At the time, the Tenderloin (what is now Pioneer Square) was widely known for being a vice district that contained the bulk of the city’s brothels, saloons, and gambling parlors. Wappenstein allowed all this illegal activity to flourish in exchange for hefty amounts of payoff money, earning the neighborhood’s denomination as “Wappyville.” It was here, amid such concentrated amounts of vice and corruption, that Margett was assigned to work as a beat cop and it’s where he quickly became indoctrinated into society’s more illicit side.  

Margett’s first year as a patrolman reflected his somewhat naive entry into such an amoral police force. He reportedly made a huge number of arrests (a strong indication that he was not initially on the take) involving illegal blackjack games, saloons selling beer to minors, and various prostitution rings. His most publicized arrests included local madame, “Big” Mabel Collins, as well as the “Cocaine King of Seattle,” C.J. Yates, who operated a drug ring disguised as a messenger service.

The young patrolman’s success as a celebrated crimefighter came to a halt in 1911. His mother, who was living in New York at the time, had been diagnosed with a terminal illness and was given only a few months to live. Margett requested temporary leave to go care for her, but his request was personally denied by Wappenstein himself.

The refusal was rather odd, given Margett’s exemplary police work. However, the number of arrests that Margett had made inside the boundaries of “Wappyville” had likely caused problems for the police chief, so this may have been a form of retaliation — a shot across the bow to let the young patrolman know that he best start falling in line if he wanted any perks of the job. For Margett, providing hospice for his mother had a higher level priority than his police career, so he submitted his resignation and promptly departed for New York.

During Margett’s time back east, it was revealed in the local papers that Seattle Mayor Hiram Gill and Chief Wappenstein were allowing illegal vice to run rampant throughout the city in exchange for payoff money, resulting in a huge political scandal. Gill was removed from office in a recall election and Wappenstein was summarily dismissed from the force. Immediately afterwards, Claude Bannick – an honest cop who was known for playing things by the book – was brought on board as the new police chief. 

After his mother’s death, Margett returned to Seattle and upon hearing about the regime change at the department asked to be reinstated as a patrolman. This time it was Bannick who denied this request – likely because the reputations of all the Tenderloin cops had been permanently tainted with Wappenstein’s lingering stench. Nonetheless, Margett remained persistent in his goal, and despite Bannick’s refusal to rehire him, he was finally allowed to return back as a patrolman on March 27, 1911, but only after a series of contentious police board hearings.

While Margett’s first term as a police officer was marked by his diligent enforcement of the law, his second term took a much different route. He was once again assigned to the vice district, though his police stats were now suddenly on par with the other Tenderloin cops. Gone were the days of his zealous arrest record. It’s unknown why there was such an abrupt shift, though he may have been bitter over the treatment he had been given by the higher-ups and so had simply resigned himself to the various ways that Seattle cops supplemented their incomes.  

The next few years of Margett’s police life were rather uneventful as far as the historical record goes. Things came to light in 1915 when he was indicted on charges of grand larceny and promptly suspended from the force. It was revealed that Margett had formed a business partnership with “saloon keeper and boss of the underworld,” Felix Crane, in which Margett was being paid to protect Crane and his “dancehall girls” from arrest.

For reasons that aren’t abundantly clear, the indictments against Margett were quietly dropped and he was reinstated back onto the force. All levels of the Seattle judicial machine were quite corrupt back then, so such charges could easily be dropped for the right price. Felix Crane, who was one of the few black saloon owners in Seattle, would later be an important part of the Jackson Street jazz scene as owner of a cabaret known as The Alhambra. He would also be one of Roy Olmstead’s top customers in the 1920s.

Soon after Margett’s return as a patrolman, Washington residents voted in favor of State Initiative 3, which banned the sale and manufacture of alcohol. As Washington became a “dry” state on January 1, 1916, booze suddenly became a very profitable black market commodity. For Margett, whose loyalty to the force ended upon his mother’s death, this new age of Prohibition represented unlimited financial opportunities. After all, he had learned the art of police graft from the very best.  

While Margett used the power of his badge to help facilitate the smuggling of illegal booze, two brothers – Fred and Logan Billingsley (shown in the photo below) – opened up the Stuart Street Pharmacy. One of the stipulations of Washington state’s new liquor laws was that “medicinal alcohol” could be obtained with a legal prescription. This resulted in a flurry of new pharmacies opening up. Some operated within the parameters of the law, while others blatantly ignored the requirements for a valid prescription and essentially became illegal liquor stores. The Stuart Street Pharmacy was decidedly in the latter category.  

It was no big surprise then that the Billingsleys were one of the first operations to be raided and shut down following a police crackdown on unlicensed pharmacies. Among the squadron of cops responsible for arresting the Billingsley brothers on that fateful day was none other than Patrolman Margett. It would be the first of many such meetings between the two parties and served as the official launching point for an eventual rivalry.    

Following the closure of their pharmacy, the Billingsleys decided to skip to the front of the supply chain and start manufacturing their own liquor. After all, why be a middleman when you can be the source? With that, the entrepreneurial-minded siblings purchased a warehouse on Westlake Avenue, built a large-scale distillery inside and went to work. Within weeks, the streets of Seattle were awash with Billingsley-brand moonshine.

Meanwhile, back at police headquarters, rumors were swirling that Margett had aligned himself with the city’s illegal liquor trade. Such suspicions were confirmed when Margett was caught in the act of tipping off a saloon about an impending police raid, resulting in his immediate dismissal from the force. By this point, though, Margett’s bootlegging career was already well underway and so he simply continued down his newly-chosen path.  

National Prohibition was still four years away, and while Washington had joined several other states in criminalizing alcohol, it was quite legal in many others. One of these remaining wet states was California, where several booze merchants had been making record profits thanks to the demand from nearby dry states. Margett was one such customer, making large purchases of bourbon whiskey from The Jesse Moore Hunt Company in San Francisco. Typically, Margett would place his order and the booze would then be surreptitiously shipped or trucked to Seattle, where Margett would then dispense it throughout the city. 

Between Margett’s bootlegging racket and Billingsley’s moonshine operation, it didn’t take long for a business rivalry to form. Adding salt to the wound for the Billingsleys was the fact that Margett had previously participated in closing down their pharmacy. Bad blood quickly developed between the two groups, and at some point Margett and the Billingsleys began hijacking each other’s booze deliveries. With tensions steadily mounting, both groups started carrying guns. A shoot-out nearly took place at a downtown garage.

With everyone on edge, the Billingsleys hired an armed nighttime security guard to watch over their Westlake warehouse. On the evening of July 24, 1916, the guard was walking the perimeter of the building when a suspicious-looking car slowly approached. Assuming it to be full of Margett’s men, the guard opened fire and a gunfight ensued. After the smoke cleared, the vehicle was revealed to be a police car with a mortally-wounded officer inside. The dead officer’s partner managed to slip out of the car and summon help. Within minutes, the warehouse was swarmed with a massive police response and the Billingsleys were promptly arrested.

A few weeks later, the Billingsleys were released on bail and went right back to work in the illegal booze industry. With their warehouse now closed down, the Billingsleys began purchasing wholesale quantities of liquor from the same source as Margett — the Jesse Moore Hunt Company in San Francisco — which fueled further animosity between the two groups. In addition to hijacking each other’s shipments (an act that earned Margett’s “Pirate Jack” nickname), the two groups also began reporting each other to the police.

In fact, thanks to an “anonymous” tip from the Billingsleys, Margett was arrested on November 3, 1916, when Seattle police raided a warehouse that was being used as storage space in his bootlegging operation. When police smashed through the front doors, they discovered 177 cases of whiskey that had just been shipped in from San Francisco. When Margett’s pockets were searched, police discovered $2,500 in cash as well as several incriminating documents from the Jesse Moore Hunt Company which detailed their business dealings.  

Margett’s arrest was celebrated throughout the city. One official declared, “The arrest of Margett is probably the most important that has been made in our attempts to rid the city of bootleggers.”  Further investigation revealed that Margett was also helping run a prostitution ring with a pimp known as “Peanuts.” As the papers reported, the two men were “employing women in the honky tonk dance halls of the bad lands.”   

With Margett now in jail, the Billingsleys were finally able to gain control of the city’s liquor trade and were now hauling weekly shipments of booze up from San Francisco in convoys of 15-20 trucks. This made their arrest a high priority for local authorities. Margett capitalized on the moment when he proposed an immunity deal in exchange for providing information to help bring down their operation, as well as testifying against them in court.

His offer was accepted. Margett spilled the beans on everything, explaining in detail how the local bootlegging business worked. The shoe was now on the other foot, and thanks to Margett’s testimony, an indictment was secured against the Billingsleys, who were both promptly arrested. Per the terms of the deal, the charges against Margett were dropped, and a few months later he would move to California, where he would marry and start a whole new life. 

In April 1917, Logan Billingsley managed to saw through the window bars in his jail cell and slip through the opening. Before fleeing Seattle, he would call the local press to boast of his escape but was eventually captured several months later in Toledo, Ohio. After serving a short prison sentence, Fred moved to Oklahoma, where he would marry and settle into a comfortable middle-class life. Logan made his way to New York where he died in 1963 as a millionaire businessman. The obituaries described him as being a “real estate man,” though no mention was made of his Prohibition-era activities in Seattle.

Likewise, Margett would also create a whole new post-Prohibition version of himself down in San Francisco. He operated a franchise of rug stores throughout the 1920s, before becoming director of a California pensions fund. In the late 1930s, Margett and the owner of the pensions operation found themselves in legal trouble after the legitimacy of their business was called into question. Bouncing back as usual, Margett opened a chain of furniture stores throughout California. There he lived a nice and comfortable life before passing away in 1954, aged 64 years. 

While the stories of Margett and the Billingsleys have been relegated to the dustbin of local history, they join Roy Olmstead in representing a narrative that is unique to Seattle bootleggers, namely the complete reinvention of themselves after Prohibition ended. It can be said that bootlegging itself was a chase of the American Dream, including second acts. 



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