Whiskey and wiretaps Whiskey and wiretaps Whiskey and wiretaps

Above: Behind her diamonds and furs, Elise Olmstead, wife of Seattle’s most notorious bootlegger, led a mysterious double life. Photo courtesy of the Olmstead family.

When most people retire, they spend time with family or explore the country. Albert Gidari, ’94, a renowned privacy lawyer, traveled back to the 1920s in search of a Seattle woman once known as the “Queen of the Bootleggers.”

His fascination began with Olmstead v. United States, a landmark Supreme Court case on wiretapping and privacy. “When you practice privacy law, one of the first cases you read is Olmstead,” Gidari says. “I was fascinated by how the wiretap worked … and what happened to the people behind it.”

Those people were Roy and Elise Olmstead. Roy, a Seattle police officer turned bootlegger, had a large, well-organized operation that managed to conduct business without violence. Elise, his English-born wife, was more mysterious: Going by a variety of names—and perhaps not legally in the country—she was rumored to be everything from hapless bystander to government spy.

Gidari already knew a few things about privacy, paper trails and the workings of government. He grew up in upstate New York, studied history at Tulane University in New Orleans and then spent 10 years in the Marines, where he worked as a judge advocate. In 1988, he joined Perkins Coie in Seattle as a litigator and pursued a UW master’s degree in environmental law. But he soon turned to technology. “Next thing you know, the internet exploded,” he says. His clients included Netscape, Nintendo, Facebook and Twitter.

As Gidari dug into transcripts and archives to satisfy his curiosity, Elise’s story took over. She fled England at 19, pregnant and alone, arrived in British Columbia under an assumed name, and eventually moved to Seattle, where she worked as a hairdresser on University Way before becoming a bookkeeper—and a government snitch—for the Northwest’s most notorious bootlegger. Then she married him.

The couple lived in a Mount Baker neighborhood mansion. She wore furs and diamonds, hosted lavish parties and read bedtime stories to children over the radio—while federal agents listened in on her husband’s phone calls. He had about 50 people on payroll and a fleet of boats. Until it all came undone in the wake of a 1924 police raid. Sensationalized by the newspapers as a glamourous figure and possibly the brains behind her husband’s business, Elise was part myth, part mystery. “The descriptions and stories about her from the trial got me hooked,” Gidari says. “She was every bit as interesting as Roy.”

The research took Gidari deep into newspaper archives and the UW Libraries’ Special Collections, tracing wiretap records, court motions and missing files. His curiosity led him to their daughter, Patricia Olmstead McFarlane, ’47, ’68, who was born in the middle of her parents’ legal troubles. “I ended up telling her things she didn’t know,” Gidari says. “And she and her children shared things with me that don’t exist in the archives.”

He found that when Elise first worked for Roy as a bookkeeper, she was also an informant for Prohibition agents—a relationship that ended abruptly as she and Roy grew closer.

Gidari is still chasing a long-lost 700-page transcript of the Olmstead wiretaps. He’s convinced more records are still out there to be discovered.

Back in the 1920s, wiretapping was the new frontier, Gidari says. “Now it’s digital surveillance.” The tools have changed, but the questions about privacy are the same.

The years of exploration led Gidari to write and publish the book, “Elise Olmstead: The Myth and Mystery of Seattle’s Queen of the Bootleggers.”

“This was an opportunity to clean up the record,” he says of his book, which was published in 2024. “It’s a uniquely Northwest story—and it deserves to be told.”