Prohibition Bootleggers: People and Trivia  

Prohibition bootleggers numbered in the many hundreds of thousands. They supplied the strong demand for alcohol. Most were very small-time operators. But many weren’t. Of course, one of the best-known was Al Capone.

Yet there were other interesting bootleggers who little-known. Yet they reveal some of the great variety among Prohibition bootleggers.


I.    A Few Prohibition Bootleggers

II.  Bootleg Trivia

III. Resources

I. A Few Prohibition Bootleggers

George Cassiday

Most members of Congress publicly supported Prohibition and its enforcement. But most of them drank alcohol. Many relied on the best-known bootlegger in Congress. He was George Cassiday. Known as “The Man in the Green Hat.” Hypocrisy was rampant during Prohibition.

Edward Donegan

Edward Donegan was an odd-job laborer in 1919. But in 1920 he became a millionaire within about four months. That’s because of his clever bootlegging scheme. Learn how he did it. Just click on his name.

The LaMontages Brothers

The four LaMontages brothers were high society bootleggers. They were members of exclusive social clubs. One brother was a graduate of Yale. Another was a champion polo player. All four LaMontages brothers were listed in the Social Register.

Roy Olmstead

This Seattle police sergeant arrested many bootleggers. He saw their many mistakes. Using a more systematic approach, he began moonlighting as a bootlegging. Then he was caught and fired. He went full-time. Within a short period of time Roy Olmstead became one of Puget Sound’s largest employers.

George Remus

George Remus. A store clerk. Optometrist. Lawyer. Pharmacist. Entrepreneur. Bootlegger. Take your pick. George Remus was all of those and more. The King of Bootleggers was even an alcohol abstainer!

II. Bootleg Trivia

prohibition bootleggers
Roy Olmstead while a police sergeant.
    • One of the most powerful prohibitionists in the country was Clarence True Wilson. He said “The only good bootlegger is a dead bootlegger.”
    • Ku Klux Klan strongly supported Prohibition and its very strict enforcement. In the face of lax enforcement, it took it upon itself to attack bootleggers.
    •  Izzy Einstein and Moe Smith were famous Prohibition agents. They spent their days arresting Prohibition offenders. In the evenings they enjoyed their favorite beverages. Those were beer and cocktails!
    • In 1928, a Los Angeles jury drank the evidence against a bootlegger on trial. They said they had to be certain that it contained alcohol. So the court had to release the bootlegger for lack of evidence.
  •  The Real McCoy
    • Bill McCoy was a bootlegger well known for selling quality imported goods. His alcohol was always “the real McCoy.”
    • The president of the Woman’s Christian Temperance Union was a hard-liner. Prohibition agents clubbed a suspected bootlegger. Then they shot his unarmed wife as she ran to his aid. Her response was simple.  “Well, she was evading the law, wasn’t she?”
    • Prohibition clearly benefited some people. Bootlegger Al Capone made over 800,000,000 in today’s dollars. That’s per year. And untaxed!
    • Bootlegger George Remus was also a lawyer. He pioneered the defense of innocent by reason of insanity. And on himself! That’s after he killed his wife.
    • In collecting evidence against bootlegger Roy Olmstead, police used wire taps on his phone. This was one of the first cases of such use. Olmsted appealed it all the way to the Supreme Court as illegal. But he lost in the landmark case of Olmstead v. United States. That was in 1928.
    • Many stills used lead coils with lead soldering. The gave off acetate of lead, a poison. Also some bootleggers used recipes that included iodine, creosote, and even a little embalming fluid.
    • The federal government poisoned industrial alcohol. It could be diverted to beverage use. The head of the Anti-Saloon League and other leaders defended this practice. But it blinded and killed thousands of people.prohibition bootleggers
    • Bootlegging still exists today. That’s because of the very high taxes on distilled spirits (liquor). They more than double the price of a typical bottle of spirits. Ouch!

III. Resources: Prohibition Bootleggers