Hosted in Des Moines by the Woodmont Country Club on the shores of Puget Sound, The Good Bootlegger’s Guild recently held a ribbon-cutting ceremony to reveal a new bronze and stone monument overlooking the ruins of the Woodmont Dock.

Photo by Melody Edmiston

The ceremony was the centerpiece of the Guild’s annual meeting, and featured Des Moines Mayor Matt Pina, Councilmember Matt Mahoney, SeaTac Councilmember Peter Kwon, Burien Councilmember Austin Bell, Washington State Senate candidate Claire Wilson, Woodmont Country Club President Rorie Zajak and Vice-President Rick Devitte, and Guild founder Steve Edmiston.

Photo by Scott Schaefer

The plaque reads:


On Thanksgiving Day, November 26, 1925, federal Prohibition agents arrested Roy Olmstead in what became known as The Woodmont Dock Raid.

Nicknamed “The Good Bootlegger” because he refused to let his men carry guns, Olmstead was deemed not guilty when the jury found he did not own the liquor unloaded that night. However, in a separate trial, Olmstead was convicted based upon controversial telephone wiretap evidence. The U.S. Supreme Court upheld the conviction.

Olmstead served four years at McNeil Island; was pardoned by President Roosevelt on Christmas Day in 1935; and his case was reversed in 1967, the year after his death.

Low tide reveals the Woodmont Dock ruins. The tall piling is known as “Old Roy.”

Woodmont Country Club / The Good Bootlegger’s Guild 

“The Good Bootlegger’s Guild” celebrates the life and times of the Northwest’s Rumrunning King, Roy Olmstead, and The Annual Meeting (a.k.a. “TGBG”) has become a summer highlight for the Woodmont community, connecting residents, historians, whiskey lovers, politicians, and legal scholars. TGBG highlights this year included a special performance of prohibition songs by Tinkham Road, whiskey education and tastings by Tacoma’s Old Soldier Distillery, and TGBG founder Steve Edmiston’s “telling of the tale” about Olmstead’s bootlegging operation, Olmstead’s capture during the dramatic Woodmont Dock Raid, a dramatic middle-of-the-night showdown with federal prohibition agents on Thanksgiving Day, 1925, his journey to the U.S. Supreme Court to contest the wiretapping of his telephone, his prison time at McNeil Island, and his pardon by Franklin D. Roosevelt.

The Guild also revealed new research about how Olmstead provided secret instructions to his fleet of rum runners by having his wife Elise read bedtime stories with embedded codes over the radio station broadcasting from inside Olmstead’s mansion. After a live demonstration of how Ms. Olmstead would have called a boat to Woodmont the night of the raid, the assembled crowd was stunned by the appearance of a vintage, 1920’s wooden rum runner boat that delivered a case of Olmstead’s own alleged brand of liquor, “Glenoldroy.” The recovered whiskey? Promptly auctioned, 8 bottles gone in 60 seconds.

The Guild has been retained as historical consultant for a new motion picture in development with the filmmakers behind the locally-produced The Maury Island Incident.

“We believe that Roy Olmstead’s story presents an amazing counterpoint to the violent reign of his contemporary, Al Capone. Our story is essentially Butch Cassidy and the Sundance Kid meets The Untouchables, and is a stunning, all-true story, that starts with the spectacular 1925 Thanksgiving Day Woodmont Dock Raid, a little black book with missing pages, and reaches all the way to the Supreme Court and President Roosevelt,” said Edmiston.

Below are photos from the event, taken by Melody Edmiston:

More about The Good Bootlegger’s Guild: