Requiem for a Bootlegger: Logan Billingsley


In The New York Times obituary announcing his death in 1963, Logan Billingsley was remembered as “a real estate developer and an authority on American Indian affairs.” The obituary highlighted many of Billingsley’s achievements, including his time as the president of the Bronx Chamber of Commerce, his founding of the American Indian Hall of Fame, and the various civic councils upon which he sat during his career. What the Times left out was his earlier career as one of the most successful bootleggers in American history.

Born in Tennessee in 1882, Logan Billingsley moved west with his family to the Oklahoma Territory to seek greater opportunities. They settled in the town of Anadarko, about 60 miles southwest of Oklahoma City. The town derives its name from the Nadarko Indian tribe; the additional “A” attached due to clerical error.

For an aspiring bootlegger like Billingsley, the location of Anadarko was ideal. Positioned just outside Indian Territory, Anadarko took advantage of the federal prohibition on the sale of alcohol within the reservations. Keenly aware of the opportunity afforded by his location, Logan Billingsley opened a pharmacy to cover his operations but it wasn’t the selling of booze that first brought Logan Billingsley to the attention of law enforcement.

When Billingsley was barely 21 years old, he became involved with and impregnated a local girl in town. Her father, upset that his unwed daughter was now expecting, forced Billingsley into a hastily arranged marriage. A few months later, Logan Billingsley fatally shot his father-in-law in the back during an altercation in the streets of Anadarko. In a remarkable feat, Billingsley’s lawyer convinced a jury the killing was an act of self-defense. With his legal troubles behind him, Billingsley turned his attention to selling whiskey.

Upon entering the Union in 1907, Oklahoma prohibited the sale of alcohol across its entire territory, Indian or not. As a “friend of the saloon,” Billingsley felt convinced that the best way to overturn this unjust law was to ignore it. To that end, Billingsley founded and served as the president for the National Bootlegger’s Protective Association, an organization that claimed 227,000 members at its peak and whose objective was to resist the temperance movement in America.

Despite his attempts to organize a liquor-based labor union, Billingsley could not avoid a series of raids targeting his bootlegging. He took this as evidence of “political persecution,” and decided to skip bail and flee Oklahoma in 1909. Years later, Billingsley settled his outstanding warrants by accepting a lifetime ban on his ever stepping into the state of Oklahoma.

Billingsley’s whereabouts over the next few years remain murky, but he spent three years running whiskey in West Virginia. It was there that Billingsley again ran afoul of the law. “Back there a fellow got licked,” said Billingsley. “[The police] seemed to think I was instrumental in it. Well, they drew up a complaint–one of the formal kind of complaints–setting forth such words as ‘shoot, stab, beat and wound.’”

Rather than face a “formal kind of complaint,” Logan Billingsley left for the larger market of Seattle. The state of Washington passed a law in 1914 banning the manufacturing and sale of alcohol. Recognizing the business opportunity and the chance to reinvent himself away from West Virginia, Billingsley opened the Day and Night Drug Store with two brothers, and quickly established himself as an up-and-coming operator in the highly competitive world of Seattle bootlegging.

One night in 1916, two policemen drove to a warehouse used by Billingsley as a distillery and storage facility. An armed watchman who patrolled the building to keep competitors from stealing Billingsley’s hooch came upon the officers. What happened next was never fully resolved, but all three men were shot, with one policeman and the watchman suffering fatal wounds. Even in a rough and tumble town like Seattle, the shootings shocked the populace. Mayor Hiram Gill ordered the police: “Get the Billingsleys.”

Arrested and guilty of the bootlegging charges he faced, Billingsley tried to take down the man responsible for shutting down his $200,000 per week operation. In a meeting with the United States District Attorney, Billingsley described bribing Mayor Gill to ensure the protection of his whiskey operation. Gill’s own arrest soon followed.

As described by Seattle historian Roger Sale, “The trial of Hiram Gill was the kind of farce that is inevitable when a mania like Prohibition hits the people.” The city of Seattle was riveted by the testimony in Gill’s corruption trial and followed the proceedings in the newspapers for weeks. Yet the entire trial was a sham. In his desire for revenge, Billingsley bribed witnesses and paid $1000 to the local Prohibitionist leader Rev. Mark Matthews to launch an investigation of Gill. Although his political career was shot, Gill escaped conviction and Billingsley went to prison.

He wasn’t there long. In April 1917, Billingsley sawed a bar of his prison window loose and shimmied through the newly created opening. He then called the local press in order to boast of his escape.

Fleeing Seattle shortly thereafter, Billingsley made his way to Los Angeles, Alaska, Miami, and Cuba. It was in Havana that Billingsley ran an import/export business he would eventually sell for $2 million dollars to finance the next version of himself in New York City.

In 1922, the Billingsley Holding Company opened the Theodore Roosevelt Apartment Building. Not just any residential project, Logan Billingsley created “the largest apartment house in the world” containing 800 units and covering 750,000 square feet. It was a remarkable addition to the New York landscape.

The next 40 years witnessed Logan Billingsley building a reputation and career worthy of praise. The attention and energy he formerly reserved for running whiskey was channeled into his role as a builder, civic cheerleader, and philanthropist. By all accounts, his violent history and illegal activities were left behind the moment he stepped into New York. In fact, it seems his last alcohol-related business was his lobbying efforts on behalf of the West Indian Rum Syndicate. Billingsley argued for lower rum tariffs and even suggested a recipe: “rum with ginger wine–warming, cures indigestion.”

In the current age, where nothing is ever truly in the past, the tale of Logan Billingsley hearkens back to a simpler time when a murdering bootlegger could leave his sins and, as Logan Billingsley’s son later said, embark on a “journey to respectability.”

Stone & Gravel (courtesy of Difford’s Guide)


  • 1½ Oz. White Overproof Rum
  • 4½ Oz. Stone’s Green Ginger Wine
  • Pour ingredients into glass with crushed ice and stir. Kiss your indigestion goodbye.


Reversing Logan Billingsley’s example, Matthew D. Plunkett is leaving New York for Los Angeles this summer, though not necessarily to begin bootlegging. Plunkett’s relationship with his father-in-law is strong, and doubtful to end in a fatal shooting.  To hear the complete story of the entire Billingsley clan, contact him directly.

Image: Orange County Archives