IN THE LATE-NIGHT hours of March 20, 1920, an unassuming boat slowly approached Meadowdale Beach — a quiet and lightly inhabited waterfront area just north of Seattle. One of the men on the boat blinked the ship’s spotlight a few times and waited for a response. From the beach, a flashlight blinked back. With this go-ahead, the boat pulled up to a small wooden dock and exchanged greetings with a crew of bootleggers who had been waiting for the delivery. This was to be a swift operation and, within minutes, crates of alcohol were being unloaded from the boat and into waiting cars.

As the last of the booze was being handed off, the entire area suddenly lit up with floodlights and police sirens. Figures swiftly emerged from the darkness of the woods, and the smugglers unexpectedly found themselves surrounded by a mix of federal Prohibition agents and local police. Some tried running but were promptly stopped when police drew their guns and opened fire. The authorities had been staking out this known smuggling spot for several weeks, and it was now looking like their long hours of hard work were finally paying off, as this usually peaceful stretch of beachfront erupted into a wild scene of flashing lights, loud shouting, violent arrests and random gunfire.

Surreptitiously taking advantage of the ensuing chaos, one of the bootleggers quietly slipped into his own car, started the ignition and hit the gas, roaring past a police barricade farther up the road. Orders were shouted for the vehicle to stop, and shots were fired, but the car managed a deft escape from one of the largest seizures of booze in the Pacific Northwest.

Unfortunately for the driver, he was recognized by one of the officers stationed at the barricade, and the next morning, Seattle police arrived at his house and placed him under arrest. It was a shocking turn of events, given that the man himself was a prominent member of the Seattle Police Department. He was immediately dismissed from the force and later released on bail.

With a family to feed, the now-unemployed man surveyed his options and, well aware of the potential profits to be made in the world of bootlegging, decided to pursue it as a full-time career. Within months, he used his inside knowledge of the business to establish himself as king of the Seattle bootleggers. Some in the press would later nickname him “The Gentleman Bootlegger,” given his disdain for violence and the ethical way he ran his business, but to most he was simply known by his birth name: Roy Olmstead.

THE EIGHTEENTH AMENDMENT prohibited the production, sale and transportation of alcohol, though it did not specify what the penalties would be if the law were violated. Wayne Wheeler, national leader of the Anti-Saloon League, took notice of this and drafted the Volstead Act, which laid out exactly how the Eighteenth Amendment would be enforced. It also introduced the new agency tasked with enforcing it: the Bureau of Prohibition. The Volstead Act initially was vetoed by President Woodrow Wilson, but his veto was overridden by both the House and Senate, thereby enacting it into law on October 27, 1919. Enforcement of the Volstead Act was to officially begin in early 1920.

Speakeasies were beginning to emerge in Seattle. Some resembled the traditional style of speakeasy, as depicted in movies, where a secret password was needed in order to gain entrance past a locked door. At the fabled Bucket of Blood, customers arriving at the clandestine Seattle location would need to knock on a heavy steel door and present a special membership card through a narrow window slit. Once the card was validated, the door would be opened and the customers allowed in.

From there, they would descend down a muraled stairway and into an ornate basement club area that was always packed with excited partygoers. The Bucket of Blood’s real name was the Hong Kong Chinese Society, but it was given its nickname due to the large tin cups that beer was served in. Servers would walk around with trays of drinks, while fashionably dressed patrons danced to live jazz. Local papers described the place as “Seattle’s most colorful, flourishing and fashionable nightclub.”

Other speakeasies simply disguised themselves as restaurants, while others acted as gambling halls, where members would wear special lapel buttons designating whether they were there to gamble, drink or both. Several houseboats on Seattle’s Lake Union also were known to have served as secret liquor clubs.

One of Olmstead’s top customers at the time was John Henry “Doc” Hamilton, who operated his first speakeasy in Seattle’s Central District neighborhood. At the time, the Central District was the nucleus of Seattle’s African-American community, with many black-owned businesses.

Hamilton’s speakeasy was quickly closed down by police, but he would later open his popular drinking establishment, Doc Hamilton’s Barbecue Pit. Despite the name, it was a fancy dinner club with an elegant and stylish interior that many have since compared to Harlem’s Cotton Club. Guests would pull up to the front and be greeted by a well-dressed doorman who would escort them to their table. Once inside, Doc Hamilton would walk around and personally introduce himself to all visitors.

The Barbecue Pit was always well-stocked with top-shelf booze, courtesy of Olmstead’s bootlegging operation, and offered a variety of delicious barbecued meats. It also served as one of the top venues for local jazz bands, so it was regarded by many as one of the city’s best music spots. In the event of an unplanned raid, Hamilton had installed a special alarm system that would allow guests the opportunity to escape.

Hamilton’s speakeasy soon became the favorite watering hole of Seattle’s business and political elite, with many important meetings held inside. The status of his clientele certainly helped keep his business from being shut down, and the Pit remained one of the city’s top speakeasies throughout most of Prohibition.

MEANWHILE, OLMSTEAD had aggressively grown his operation to become the area’s top bootlegger. At this point, he was sending his speedboat, the Zambesie, on regular runs to Haro Strait to pick up prearranged shipments of Canadian booze at D’Arcy Island.

This particular island was strategically chosen by Olmstead, as it was surrounded by dangerous reefs and was also the site of a leper colony. Because of this, visits by unwanted guests were rare. He had even made financial arrangements with the leper keeper to serve as a lookout, and before long, the island was serving as his official Canadian pickup point.

After the ship was loaded with booze, his crew would then wait until evening, just as the sun was setting, for the perilous voyage back across Puget Sound. To help minimize the risks of being caught by the Coast Guard, Olmstead had spotters in strategic locations such as Port Angeles and Port Townsend. If a rumrunner received an “all clear” from the spotters, he would then speed down to various docks throughout Tacoma, Seattle and Everett.

From there, the booze would be loaded into waiting delivery trucks and brought to temporary holding spots, usually parking garages and warehouses, to await delivery to the city’s speakeasies, soda shops and private social clubs.

Olmstead paid off police officers on harbor boats and patrol cars to serve as lookouts for his operation. All his years spent on the force gave him an intimate knowledge how the Seattle Police Department operated. He knew their schedules and procedures, as well as who could be paid off and who couldn’t. As a result, a large majority of the city’s police force had its bank accounts padded thanks to Olmstead. In fact, the running joke at the time was that Olmstead commanded more officers as a bootlegger than he ever did as a police officer. This proved to be a frustrating experience for federal Prohibition agents, though, as they could never get quite close enough to observe his operations, much less catch him in the act.

Further establishing himself as a savvy and brilliant businessman, Olmstead figured out a way to avoid paying Canadian export duty tax on his liquor, which allowed him to sell his alcohol at prices significantly cheaper than his competitors. To do this, he took advantage of a trade agreement between Canada and Mexico.

The Canadian government had become wise to the staggering number of alcohol shipments going to the thirsty American market, which, to them, represented a potentially large sum of missed tax revenue. As a result, Canada imposed an export tariff of $20 per case for all American-bound shipments of alcohol. Olmstead exploited this by hiring cargo ships in Vancouver and loading them with large amounts of alcohol, sometimes up to 4,000 cases. He would then have the documents falsified or forged to make it look like the ships were bound for Mexico, thereby avoiding this $20-per-case duty tax. This enabled him to undercut his competitors by as much as 30 percent and establish his dominance in the local market.

Soon, he was smuggling 200 cases of liquor per day, and earning $200,000 per month. This was a huge sum of money in the early 1920s, especially compared to his previous salary as a police officer. Before long, Olmstead could be seen driving around in luxurious cars while dressed in dapper suits. He purchased a palatial estate in the Mount Baker neighborhood, where he threw some of the most lavish parties in the city. If he was “king of the bootleggers,” he figured he might as well look the part.

EDWIN J. (“DOC”) BROWN won the 1922 Seattle mayoral race in a landslide victory. Immediately upon assuming office, Brown let it be known that if the federal government wanted Prohibition enforced, then federal agents should enforce it themselves. He also believed that imported alcohol was safer than street-level moonshine and ordered his police force to concentrate on people selling “bad booze” rather than harass any of the bootleggers. In fact, he was quite cozy with some of the local underworld.

Adding to this was Brown’s permissiveness toward Olmstead, who was quickly becoming famous as the “Gentleman Bootlegger” due to the ethical ways in which he conducted his business.

Olmstead’s number-one rule was that his men would not carry guns or engage in any manner of violence. He believed that guns invited problems that could just as easily be solved by paying people off. Number two: His men would act and treat others with respect. He was running a professional operation and would not tolerate any thuggish or boorish behavior from any of his employees. Number three: He would not be involved in any prostitution, gambling or narcotics. Despite Prohibition laws, bootlegging was widely viewed as a respectable profession, and he strove to keep his business within such limits. Lastly, he would sell only premium bonded liquor from Canada. Nothing inferior or watered down, nor would he sell anything stolen or hijacked. If you bought your alcohol from Olmstead, you knew you were getting the best stuff available on the market. As a result, all of Seattle’s elite private clubs stocked his booze, including the Rainier Club, the Arctic Club and the Butler Hotel. The top speakeasies also purchased from Olmstead, including Doc Hamilton’s Pit.

The local press loved him, as did the citizens of Seattle. For many, Olmstead represented a safe way of obtaining good-quality alcohol that wasn’t tainted by other criminal activity. As a person, he was friendly, approachable and had a great sense of humor. He was a common fixture on downtown streets, always willing to pose for a photograph or share a lighthearted conversation.

On any given day, he could be seen talking to people from all walks of life, from a lowly street sweeper to the Rev. Mark Matthews. His business empire had grown to the point that he had become the area’s largest employer, with a massive local workforce of clerks, drivers, swampers, dispatchers, mechanics, warehousemen and legal advisers. He was Seattle’s “good” bootlegger, and people throughout the city adored him.