Bootlegging at Des Moines Marina

Learn about Roy Olmstead, "The Good Bootlegger", and his role in the secret culture of bootlegging during prohibition, and how Des Moines was a key location to deliver smuggled alcohol.


Watch the Seattle Southside Scenes Video on Bootlegging at Des Moines Marina

A film by Steve Edmiston. To learn more, visit Quadrant 45.


When you think of prohibition, what is the first story that comes to mind? Do you like gritty, real-life rise and fall stories of prohibition gangsters like Lucky Luciano, Meyer Lansky, Bugsy Siegel, and of course Chicago's notorious Al Capone? But what if there was a strikingly different kind of prohibition story with a final shipment and a late-night raid on a lonely dock right here in Des Moines in Seattle Southside?

The Des Moines Marina is a marvel, and the fishing pier is the crown jewel. So, what better location to launch the absolutely true story of the good bootlegger Roy Olmstead and his final action-packed arrest on the Woodmont Des Moines dock Thanksgiving Day 1925.

Roy Olmstead becomes a Seattle policeman in 1907 at the age of 21, along with his brothers Frank and Ralph. Roy was good. He is hand-picked for Mayor Hiram Gill's ultra-violent dry squad at a dangerous time where the police squared off against rival gangs with lethal results. Olmstead can see that the flow of illegal liquor is about to be completely shut off by the feds. He is convinced he can do better, so Seattle policeman Olmstead forms a gang to enter the bootlegging business. But only one month into prohibition, Olmstead's caught. He's fined. He's fired. He decides to take over bootlegging in the Northwest. He'll do it with plenty of bribes, but he also adopts a code: no guns. The press gives him a new nickname, 'The Good Bootlegger' and by the time Al Capone commits his first murder in 1923, Olmstead's Seattle operation delivers over 200 cases a day, and he grosses (in today's dollars) over 35 million a year.

But all that success attracted the prohibition bureau and they wanted Roy Olmstead bad. And they fought back with two key tools. First, there was this brand-new technology called wiretapping. The second tool the feds had was an informant. Olmstead's protege, Al Hubbard, secretly joined the prohibition bureau. The wiretaps and the informant led to a raid and 17 arrests at Olmstead's house but he is out on bail the very next day conducting business as usual. But just over one year later for the first time Hubbard confirms to the feds that Olmstead will try to land liquor at a dock in Seattle Southside, the Woodmont Dock in Des Moines, Thanksgiving Day. And for the first time, Olmstead himself will be there. When Olmstead's speedboat, The Three Deuces, begins unloading, federal agents rush down an embankment with Tommy guns at the ready and trap Olmstead and his men on the dock. 240 cases of booze are seized but for some reason only 110 cases make it to impound. As always, Olmstead had no gun.

Olmstead's 1926 trial is the biggest trial ever held during prohibition. Olmstead's defense is that the evidence was obtained illegally by wiretap. His case is appealed all the way to the United States Supreme Court. In a five to four decision upholding the conviction, it is the dissent from Justice Lewis Brandeis that survives the test of time. But Olmsted's trial for what went down here in Des Moines during the Woodmont Dock raid has a happier ending. Olmstead's defense: the liquor seized was not his. The verdict: NOT GUILTY.

The Woodmont Dock is now in ruins. The Des Moines Good Bootleggers Guild celebrates Old Roy's final shipment with an annual toast at this private monument. But if you want to capture the feel of a bootlegger's run to the dock, take a walk out on the pier and stand tall over the darkening sound at dusk. Feel the air cool and the wind build and travel back in time a hundred years at this very spot and contemplate for a few moments the good bootleggers last delivery.


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