How to Bootleg Nicely

Seattle police officer turned rum runner Roy Olmstead was appalled by the violence of early Prohibition. So he decided to do things differently.

“No amount of money is worth a human life,” Roy Olmstead famously cautioned his bootlegging workers. Born in 1886, Olmstead was a young Seattle police lieutenant turned leader of a rum-running operation in the Pacific Northwest. After being discovered for his criminal activities in 1920, he was fired from the force and transitioned to being a full-time alcohol smuggler. He ran his operation like a business. He forbade members of his organization to carry a gun, and encouraged his bootleggers to use bribes rather than violence during conflicts.

The backdrop of Olmstead’s activities was the early Prohibition period in Washington, when the state banned alcohol in 1916 before the federal government did in 1919. Olmstead would begin his operation after witnessing the violence and chaos during the early Prohibition period. He refrained from diluting alcohol with toxins to cut costs, and did not organize narcotics, gambling, or gun-running—unlike his counterparts. His practices eventually earned him the title of the “Good Bootlegger.”

Humanities Washington speaker Steve Edmiston is a lawyer and screenwriter with a passion for storytelling. A self-described microhistorian, he dives deep into the story of Roy Olmstead for his talk, and the cultural and constitutional implications of Olmstead’s activities as a 1920s rum runner and bootlegger.

This interview has been edited for length and clarity.

Humanities Washington: How did you choose this topic? What drove you towards Olmstead?

Steve Edmiston: I learned a decade ago that our dock called the Woodmont Dock was the site of the most notorious bootlegger in the Pacific Northwest. I couldn’t believe I didn’t know the story. Living here for as long as I have, nobody in the neighborhood knew the story of Roy Olmstead’s arrest on Thanksgiving Day in 1925. It’s a wonderful story.

And what happens in microhistory is you sort of kick the rock and look what’s underneath. Sometimes, that’s all there is. And then sometimes there’s a huge story hiding that’s kind of been forgotten, and I felt that about Roy Olmstead and Northwest bootlegging. So that’s why I got into this subject.

Why did Olmstead, a police officer, turn to bootlegging in the first place?

My conclusion is that Roy Olmstead wasn’t just trying to make a buck as a bootlegger. I believe Olmstead had a plan to bring some order to the chaos throughout the Pacific Northwest [during Prohibition], particularly in Seattle. The idea was, “If we’re going to have a violence model of Prohibition, what if I go into bootlegging and rum running and do it differently? I’ll do it all without violence. I’ll even have a rule that no one in my operation can ever carry a gun. And I will never have my operation do any other kind of vice,” [the latter of which] was the standard all over the country. If you went into rum running, you were also usually into prostitution and drugs and every other kind of vice. So if you get inside his head, and you’re really trying to think of him as a character and ask, Why is he doing it? He’s saying, “I can make a lot of money, but can I make a lot of money giving people what they want and I’m going to reduce the level of violence in my community.” He’s a really interesting character.

What were the pieces of evidence that led you to that conclusion?

I see Olmstead as an antihero, very similar to the classic Butch Cassidy and the Sundance Kid model, where you have these gentlemen bandits that don’t want to hurt anybody. And everybody kind of loves them, even though they’re committing crimes. I stumbled upon a piece of research, a great article about homicide rates in the 1920s and how they were impacted by Prohibition. The study was fascinating because it really broke down by major cities the homicide rate. So in 1900, our homicide rate was about 10 per 100,000. If we buy into the theory that prohibiting a popular illegal substance will lead to illegal activity, then we would expect the rates of illegal activity will climb. And homicide rates do skyrocket around the country. The same studies show that in Seattle, interestingly enough, our homicide rates go up from 1916 through 1919 when Olmsted’s a cop and the gangs are running alcohol. But when Olmstead becomes a bootlegger, the rates drop from 1920 to 1927.

That to me is a really great piece of evidence to suggest that there’s a fundamental difference between this notion of a violence-driven model of Prohibition and this really weird experiment going on here in the Northwest with a gentleman criminal, Roy Olmstead, running an operation with no guns. I just found it phenomenal.

He’s saying, “I can make a lot of money, but can I make a lot of money giving people what they want and I’m going to reduce the level of violence in my community.”

Tell me about the Supreme Court Case Olmstead v. the United States and why it was so important.

The trial is in fact the largest trial in the history of Prohibition in the United States of America. The original indictment was against 89 conspiring defendants. It’s nicknamed the Whispering Wires case, because of the wiretapping that was underway. [Olmstead’s] defense at the trial was that his rights of privacy were violated and there was an illegal search and seizure without a warrant using these wiretaps. But the defense doesn’t get him anywhere, and he is convicted. That case goes through the Court of Appeals where he loses, and it ultimately lands at the Supreme Court in Olmstead v. United States. It comes down with a 5-4 decision in 1928, which upholds the conviction.

It’s fascinating that the majority opinion is written by Chief Justice Taft, who tries to explain that we have to allow law enforcement to bend the rules from time to time, or the criminals will get away with stuff. But the part of the opinion that certainly stands the test of time is the dissent that’s written by Justice Louis Brandeis. He writes that all of us have rights and we can’t allow the Prohibition Bureau to break laws to enforce laws. But even more interesting is how he predicts the future. He’s predicting that the rate of technology will never slow down.  And so Brandeis is basically saying, we always have to have probable cause and a warrant if we’re going to violate someone’s privacy.

In 1967, the year after Olmstead dies, Olmstead v. the United States is reversed by a case called Katz v. the United States. This relied on Justice Louis Brandeis’ dissent and is now the law of the land. The Olmstead Supreme Court case has had a huge impact on our society and still does to this day.

What drives you to storytelling?

Well, I guess I have a very personal answer for that. My dad, who’s passed away, was a history teacher in high school for 33 years at Tyee High School. I need to confess that he was an amazing storyteller. I remember coming home in the evenings and the way they talked was all these great, great stories. And my dad would always talk about dialogues. For me as a kid, in a sense, it didn’t take that I enjoyed the storytelling.

But I found, as I got older, that working as a lawyer, screenwriter, and running a game company, everything I did, actually, always came from story. I always talk about law as sort of combat storytelling and screenwriting is obviously just, you know, storytelling.

I discovered in the game business that we were always just telling stories and creating a world that people want to engage in this world. I think I came to story professionally. That’s when I came kind of came full circle to my dad’s fascination with history. And it definitely was triggered by discovering these stories in my local community. Now I’m hooked.

The other thing is there’s a little part of me that sees finding history as a treasure hunt. I think that’s what microhistorians do well. I think that when you find stories that have been lost, because they’ve just been elbowed out by the dominant narrative. And you are able to kind of suss them out and raise them up. That’s exciting. That’s finding the treasure and sharing it with the community. Because if you don’t do it, it just stays lost. And there’s sort of an excitement there to raise that up.

Steve Edmiston is giving his last Speakers Bureau talk on Roy Olmstead on Wednesday, December 6, in Kent. MORE >

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