King of the Bootleggers

New York City Deputy Police Commissioner John A. Leach, right, watching agents pour liquor into sewer following a raid during the height of Prohibition, ca 1921 (Library of Congress).

Prohibition days certainly encouraged “rum-running” and “bootlegging,” and many became very proficient at the game.

But how could a once-honest cop possibly turn into an infamous bootlegger?

Roy Olmstead as a young police officer in Seattle. Early 1900s.

I love discovering characters from the past that were just a little different from the rest. Crossing the line of respectability made them that much more intriguing.

And such a man was Roy Olmstead from Seattle.
​
He was born on a farm in Nebraska in 1886 and was raised by good farming folk to become an upright citizen. In 1907, he joined the Seattle Police Force, following in the footsteps of his older brother.

And by 1910 he had been promoted to sergeant.

---

PROHIBITION DAYS
In 1916 Washington joined the “dry" states as a result of prohibition, and a year later, Joe Warren was appointed Seattle chief of police. He soon noticed Olmstead’s diligent work and squeaky clean record so by 1919 had appointed him to lieutenant.

Although not officially working on the “dry squad” himself, Olmstead soon became very familiar with the way bootleggers operated as they plied the waters of the Pacific Northwest between Seattle and Vancouver Island. Many of them made money while others continued to just make mistakes so they were caught. Olmstead realized where they went wrong and was convinced he would do much better at the game.

So he began to operate his own small bootlegging business, believing that working on the other side of the law would be a piece of cake! Unfortunately, he too made mistakes and was soon caught, fined, and eventually dismissed from the police force.

That didn’t bother him, because he had wanted to go into the bootlegging business full time anyway. Eventually he became one of the largest bootlegging operators and employers in the Puget Sound.

THE BOOTLEGGER
By 1924, his operation was so successful that he was able to wholesale liquor to numerous clients, many of whom were Seattle’s elite and even some police officers who turned a blind eye to what he was doing.

At the height of his career as a bootlegger, Olmstead’s organization alone was delivering 200 cases of Canadian liquor into the Seattle area daily, and he was grossing $200,000 a month. He owned a fleet of vessels and had purchased a farm outside town to store the contraband goods.

Strangely, he never allowed his men to carry guns. He believed it was better to lose a shipment rather than lose a man’s life. This was quite a departure from other bootleggers at the time and certainly contrasts today’s views of owning guns in the US.
​
But soon Olmstead was caught, and his operation came to an end. On January 19, 1925, Roy and his second wife, Elise, were both arrested.

Elise and Roy Olmstead, 1925. (Museum of History and Industry).

Elise Olmstead (using the name “Aunt Vivian”) had been broadcasting children’s bedtime stories over a radio transmitter from one of the bedrooms in their elegant home. In point of fact she was really sending out coded messages to rum-running vehicles!

Many in Olmstead’s organization were also arrested and two of his vehicles, the Eva B and the Three Deuces were seized and over 700 cases of liquor and 240 cases of contraband goods were confiscated.

Olmstead’s Trial became one of the largest and most controversial in US history.  Olmstead was sentenced to four years in the McNeil Island Federal Penitentiary and fined $8,000. His wife, Elise, and seven other defendants were acquitted.

Having studied the law well and with his wife’s help from the outside, Olmstead made frequent appeals to the higher courts during his incarceration, and in February of 1928, the Supreme Court heard the famous Olmstead v. United States case. His lawyers claimed that wiretapping set up by the Prohibition Bureau was illegal.

In May of 1931, Olmstead was finally released from prison, and on Christmas Day 1935, President Franklin D. Roosevelt granted Roy Olmstread a full pardon, restoring all his constitutional rights plus canceling the $8,000 fine and another $2,288 in court fees.

A CHANGED MAN
By then Olmstead was a changed man. While in prison, he had embraced the Christian Science faith and now believed that liquor was a curse!

Following his release, he made a living as a furniture salesman and his wife divorced him, maybe finding him less appealing as an honest man. He began to visit prisoners in the King County Jail, preaching to them about the evils of drink! He even became a Sunday school teacher, and many alcoholics were released into his custody for counseling.

---

Roy Olmstead the “good cop” had returned. You can read more of his story in my book Legends, Liars and Lawbreakers.
​
But what, I wonder, happened to all those rum-running boats? Two of them (the Eva B and the Three Deuces) were seized by customs officials during the 1920s. During WWII,  George E. Murry was the officer in charge of a boat called the Zev, which he believed had once belonged to Olmstead. The Zev had been confiscated by the US Coast Guard Reserve and later put into service by them based in Elliott Bay in Seattle.

​There were a fleet of other boats that had once plied the waters of the Pacific Northwest. Does anyone have any information about what happened to any of them?

If so, please leave a comment below. I’d love to hear from you.

---