On Capitol Hill I am known as ‘The Man in the Green Hat’
When it comes to eating, drinking and having a good time in general, they are as human as other folks
Waiting for the train to D.C., the man in the green hat dropped his suitcase carelessly on the ground. Something shattered inside, sending its contents leaking onto the Penn Station concourse floor.
“Say, buddy,” a fellow traveler helpfully noted, “your clothes are leaking.”
It was a small operation – one devoid of the ties to organized crime that dominated much of his competition. He often traveled up to New York City and Philadelphia to port the wares himself, sometimes enlisting his wife or friends, for an extra set of arms. Accidents like this were inevitable, if uncommon.
George Cassiday had a few run-ins with the law over the course of a decade. Notably, in 1925, police raided his home and confiscated his stock. Wearing his signature light green felt hat at the time earned him a nickname. Owing in part to the 1924 publication of best-selling author Michael Arlen’s The Green Hat, the name stuck.
The charges didn’t.
Four years later, however, another arrest brought a more serious penalty. Cassiday’s book of clients was confiscated, and the bootlegger was sentenced to 18 months in jail. Even his toughest sentence arrived with caveats, however. "My mom and him both told me he actually never spent a night in jail," his son Frederick would note, decades later. "He would go there in the morning every day, sign himself in, and then, at the end of the day, sign himself out."
The reason for such leniency would be revealed to the world the following year, through a bombshell series of six articles published on the front page of The Washington Post, beginning with, "Rum Buyers in Capitol Indicted as Law Violators by Cassiday.”
The bootlegger confessed,
For nearly ten years I have been supplying liquor at the order of United States senators and representatives at their offices at Washington. On Capitol Hill I am known as ‘The Man in the Green Hat. It may be a surprise and a shock to many good people to know that liquor has been ordered, delivered, and consumed right under the shadow of the Capitol dome ever since prohibition went into effect.
Following the end of the first World War, the military veteran with was unable to return to his pre-war job at the Pennsylvania Railroad. Cassiday’s struggle to find employment coincided with the ratification of the Eighteenth Amendment at the end of 1918. He described his bootlegging beginnings as a sort of happy accident.
“A friend of mine told me that liquor was bringing better prices on Capitol Hill than anywhere else in Washington, and that a living could be made supplying the demand,” he told The Post. Operating out of a Washington Hotel, Cassiday’s first two clients were a pair of southern congressmen who had voted for the amendment. He was aware of the irony, and would carry it around for the following decade.
“It was not long before I had the run of the Senate and House Office Buildings and was spending more time there than most of the representatives,” he added. His earliest southern clients had a taste for moonshine, though he would ultimately graduate to whiskey as more northern congressmen signed on. The man in the green hat became a fixture on Capitol Hill, smuggling bottles into the building under his coat.
Complaining about the supply bottleneck one member of congress asked Cassiday, "did it ever occur to you it would be easier to bring in larger lots and distribute it from a base of operations from the inside?" Soon his operations moved to the basement of the Cannon House Office Building, where he could bring alcohol in by the crate.
Along with the confiscation of his black book, the 1925 arrest lost him his base of operations. Soon enough, however, he relocated to the Russell Senate Office Building, serving members of the higher congressional chamber. The new client base was both more cordial and discreet, with Cassiday primarily operating through secretaries, rather than the politicians themselves.
“Some of them I found were mighty good fellows," he noted, "and others not so good, but I learned right off the bat that when it comes to eating, drinking and having a good time in general, they are as human as other folks."
After multiple raids, Cassiday’s operations were a kind of open secret on Capitol Hill. Though, in spite of widespread patronage of his services, not everyone was on-board. It was Hoover’s Vice President, Charles Curtis, who finally put an end to things, enlisting a “dry spy” to take down Cassiday once and for all. A sting nabbed the bootlegger with six bottles of gin in a Senator’s parking lot.
“As the result of my experience on Capitol Hill since prohibition went into effect I would say that four out of five senators and congressmen consume liquor either at their offices or their homes,” Cassiday would report. After prohibition ended, he found a job at a shoe factory, before moving onto roles at various D.C.-era hotels. He died in 1967, having never named any of his clients.
Sources:
Prohibition in Washington, D.C.: How Dry We Weren't by George Peck
John Kelly's Washington: Congress Winks at Prohibition in Bootlegger's Tale https://www.washingtonpost.com/wp-dyn/content/article/2009/04/26/AR2009042602479.html