Prohibition Bootleggers: People and Trivia  

Prohibition bootleggers numbered in the many hundreds of thousands. They were needed to supply the strong demand for alcohol. Most were very small-time operators. But many weren’t. One of the biggest and certainly the best-known, of course, was Al Capone.

Here are other interesting bootleggers who remain little-known. They reveal some of the great variety among 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, “The Man in the Green Hat.”

Edward Donegan
Edward Donegan was an odd-job laborer in 1919, who, in 1920 became a millionaire within about four months through his bootlegging scheme. Learn how he did it.

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 championship polo player and all were listed in the Social Register.

prohibition bootleggers

Roy Olmstead while a police sergeant.

Roy Olmstead
This Seattle police sergeant arrested many bootleggers. He saw their lack of organization any their many mistakes. Using a more systematic approach, he began moonlighting as a bootlegging. After being 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!

Bootleg Trivia

    • One of the most powerful prohibitionists in the U.S., Clarence True Wilson, argued that bootleggers should be killed. He insisted that ‘The only good bootlegger is a dead bootlegger.’
    • Ku Klux Klan strongly supported Prohibition and its strict enforcement. In the face of lax enforcement, it took it upon itself to attack bootleggers.
    • After a busy day arresting bootleggers and other Prohibition offenders, famous Prohibition agents Izzy Einstein and Moe Smith enjoyed sitting back and enjoying 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 go be certain that it contained alcohol. The bootlegger had to be released for lack of evidence.
    • 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, upon learning that government agents had clubbed a suspected bootlegger then shot down his unarmed wife as she ran to his aid, responded “Well, she was evading the law, wasn’t she?”
    • Prohibition clearly benefited some people. Notorious bootlegger Al Capone made over 800,000,000 in today’s dollars…per year untaxed!
    • As a lawyer, the bootlegger George Remus pioneered in using the defense of innocent by reason of insanity.
    • 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. He lost in the landmark case of Olmstead v. United States. It’s 277 U.S. 438 (1928).
    • Many stills used lead coils with lead soldering, which gave off acetate of lead, a dangerous poison. Some bootleggers used recipes that included iodine, creosote,  and even a little embalming fluid.
    • The federal government intentionally poisoned industrial alcohol that could be diverted to beverage use. The head of the Anti-Saloon League and other leading Prohibitionists defended this practice that killed thousands of people.
    • Bootlegging still exists today because of the very high taxes on spirits. They  more than double the price of a typical bottle of whiskey, rum or other distilled spirits beverage.

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