The term “gangster” has its American roots in the illegal booze trade of the prohibition era: gangs of men and women smuggled booze by boat (rumrunners) and truck (bootleggers) over the Canadian border to sell in the US. But the history of Seattle area gangsters is both more interesting and far less violent than those of more notorious operations in cities like Chicago, Philadelphia, Buffalo and New York. Where the latter resorted to crime and violence, our gangsters took a more innovative approach to getting folks their tipple. 

Washington’s prohibition started in 1916, four years before nationwide adoption. That head start, plus our proximity to Canada, made the Northwest the apex of the booze trade west of the continental divide. But getting Canadian hooch past the Coast Guard and transporting it to thirsty customers was risky business. Northwest gangsters took those risks and their investors profited handsomely. 

Gangsters built wicked-fast boats using engines pilfered from Boeing’s fleet of surplus WWI aircraft to outrun the Coast Guard. These engines made the boats so loud that locals nicknamed them “fireboats” and their cargo “firewater.” By 1917, the ship canal opened a waterway from the Puget Sound to Lake Washington, ideal for getting booze into the interior. Kenmore and Bothell became the distribution gateway for locations north and east of Seattle. Fireboats would offload in Kenmore where the cargo was either bootlegged by land for storage in Bothell and distribution north or loaded onto boats and transported along the Sammamish River for distribution east. Powered by paddles, these boats traveled silently and only at night, giving them the name “shadow boats” and making them one of the most effective and least-busted means of firewater transport.

As trade in illegal booze intensified, gangster leaders coordinated their fleet movement via AM radio, using coded messages cleverly hidden among the idle banter and broadcast shows. One such radio station was run by the wife of the most successful Northwest gangster, former police officer Roy Olmstead.

The destination of much of this booze was so-called speakeasies and bottle clubs. These illegal bars and nightclubs operated underground behind secret doors and accessed with whispered code words. The most infamous speakeasy was the Bucket of Blood in Pioneer Square, named for the color of its homebrewed beer. In the Bothell area, the term bottle club was more prevalent. 

But what set the northwest gangsters apart from the violent gangs that served cities like Chicago and New York, was their refusal to operate shakedowns, gambling, prostitution, and drugs that gave the gangsters of other cities such a bad name. Our gangsters became known as Gentlemen Bootleggers. They were innovators and respectable members of their community. Indeed, after prohibition was repealed, many went on to careers as politicians and clergy. 

At Side Hustle, our taprooms celebrate this history by serving beer from our Original Gangster Brewing Company and its sister Bellevue Brewing, alongside rotating guest taps and cider from The Republic of Cider. Now we may or may not operate a secret bottle club. But that is for us to know and you to find out!