While Americans were expected to comply with the ban on alcohol enacted by the 18th Amendment and the Volstead Act, many of the very same members of Congress who supported Prohibition would come to rely on George Cassiday, a.k.a. the Man in the Green Hat, to make sure their liquor cabinets never ran dry.
A military veteran, Cassiday’s foray into bootlegging began after World War I when he found himself unemployed and in desperate need of a job to support his family. After a friend suggested bootlegging on Capitol Hill as a way to make good money, Cassiday took a chance on a new career.
In the book “Prohibition in Washington, D.C.: How Dry We Weren’t,” author Garrett Peck writes, “That friend introduced him to two southern congressmen — both of whom had voted for the Eighteenth Amendment and the Volstead Act — and he agreed to procure for them a supply of liquor.”
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Cassiday’s business spread by word of mouth and eventually grew to include hundreds of lawmakers. Since Cassiday risked exposure bringing liquor directly into the House Office (D.C.’s oldest congressional office building) he was given the keys to a private storeroom located in the basement to help streamline his operation.
“Once inside, Cassiday’s operation was remarkably low-risk. Everyone else had to open their bags for U.S. Capitol Police to inspect when they left the building, but not congressmen,” Peck writes.
Cassiday would later estimate that he delivered 25 orders on an average day. According to The Washington Post, “Cassiday got the booze from New York City and later Philadelphia, taking the train north and returning with two suitcases groaning under the weight of 40 quarts of alcohol.”
Cassiday continued peddling booze in the House Office until he was arrested in 1925, leading to his banishment from the building. That incident would also be the origin for his moniker. At the time of the arrest, Cassiday was wearing a green felt hat, the details of which were relayed to the press.
Undeterred by his setback, Cassiday switched his business to supplying booze to the Senate Office Building. In 1930, he was arrested delivering six bottles of gin to the senators’ parking lot and forced to give up his client book. Cassiday was sentenced to 18 months in jail, though it appears he only “sort of” served the time, spending his days in jail and “signing out” at night.
Later that year, The Washington Post would release a five-part exposé in which Cassiday detailed his decade of bootlegging on Capitol Hill, though he never revealed the identities of his customers.
In 2012, the D.C.-based distillery New Columbia Distillers paid homage to Capitol Hill’s official bootlegger by naming its product Green Hat Gin after Cassiday, making sure to clear their request with Cassiday’s son before officially christening the product.