One day in March 1925—five years into the absurd experiment called Prohibition—a dapper man named George Cassiday strolled into the office building of the U.S. House of Representatives, carrying a briefcase and wearing a spiffy light green hat. The cop at the door recognized Cassiday, which wasn’t surprising. Nearly everybody on Capitol Hill knew Cassiday. He was Congress’ favorite bootlegger, working out of the House Office Building, delivering booze to dozens of congressmen, who found a strong drink soothing after long days spent listening to tedious political blather.

On this day, however, the cop stopped Cassiday, inspected his briefcase, found liquor and arrested him.

When reporters heard that a bootlegger was busted in Congress, they called the House sergeant-at-arms, who described the miscreant as “a man in a green hat.” The next morning, Cassiday became famous across America as “The Man in the Green Hat,” a living symbol of congressional hypocrisy and the follies of Prohibition.

Cassiday pleaded guilty and served 60 days in jail. When he got out, he learned that he’d been barred from the House Office Building. Obviously, he needed another place to work. So he moved to the Senate Office Building. He sold booze there for five years, until 1930, when he was arrested delivering gin to the Senate. This time Prohibition agents confiscated Cassiday’s “little black book,” containing the names of his illustrious customers.

In October 1930—two weeks before the congressional election—the Washington Post announced that it would publish a six-part series written by Cassiday, revealing the juicy details of his adventures as Congress’ “official bootlegger.”

“It will be,” the Post promised, “an astonishing story.”

And it was.

“For nearly ten years, I have been supplying liquor at the order of United States senators and representatives at their offices,” Cassiday began. “On Capitol Hill I am known as ‘The Man in the Green Hat.’ ”

Born in West Virginia in 1894, son of a steelworker, Cassiday quit school after the third grade to work in a glass factory. When World War I began in 1914, he joined the army of the United Kingdom, his mother’s birthplace. When the United States entered the war in 1917, he transferred to the U.S. Army.

Fighting in France, he received rations of cognac and learned how to drink. Sailing home on a troop ship in 1919, the soldiers held a vote on the hottest issue of the day—Prohibition. As Cassiday later recalled, only 98 of the 2,200 soldiers voted to ban booze.

Back home, Cassiday married and settled in Washington, D.C. He was searching for work in 1920—the first year of Prohibition—when a friend suggested that he sell bootleg whiskey to thirsty congressmen. “I thought he was joking,” Cassiday wrote.

George Cassiday in 1930, the year the Washington Post published the story of Congress' "official bootlegger." (Library of Congress)
George Cassiday in 1930, the year the Washington Post published the story of Congress' "official bootlegger." (Library of Congress)
But the friend introduced him to two Southern congressmen eager to buy moonshine. Both had voted for Prohibition, but that didn’t affect their thirst, and they had equally thirsty colleagues. “I soon got over any feeling that these men in Congress, just because they were supposed to be big statesmen, were any different from other people,” he wrote. “When it comes to eating, drinking and having a good time in general, they are as human as other folks.”

At first Cassiday’s customers were Southerners who enjoyed moonshine, but soon he acquired Northern customers who demanded genuine bourbon, real rye and imported scotch. Cassiday found a supplier in Manhattan and he’d travel by train to New York, load 40 quarts into two large suitcases, then return to Washington.

One day he set a heavy suitcase down a bit too hard on the floor of Penn Station, breaking several bottles. As he hustled toward the train, whiskey dripped from the suitcase, emitting its unmistakable aroma. “Say, buddy,” a grinning bystander yelled, “your clothes are leaking.” Cassiday boarded the train, ducked into a restroom and cleaned the suitcase. “Most of the bottles were intact,” he wrote, “and were delivered in good order to customers on Capitol Hill.”

His business boomed. Congress had voted overwhelmingly for Prohibition, but Cassiday estimated that four out of five congressmen and senators imbibed. He was selling to scores if not hundreds of pols—and he wasn’t the only bootlegger serving them. But he had one vexing problem: Every day, Cassiday had to carry briefcases of illegal liquor past the Capitol police. Fortunately, one customer—a Midwestern congressman he declined to name—suggested a solution.

“George,” the congressman said, “did it ever occur to you it would be easier to bring supplies into the building in larger lots and deliver it from a base of operations on the inside?”

With his powerful friend’s help, Cassiday obtained an office in the House Office Building. It became his warehouse and also served another purpose: When customers’ demands exceeded supply, Cassiday simply created more booze in his hideaway.

“Using one gallon of pure rye whiskey as a base, adding one gallon of pure grain alcohol and one gallon of hot water from the spigot, and adding a little bouquet coloring,” he wrote, “I found it was possible to turn out 12 quarts of 86 to 96 proof that was entirely satisfactory.” That dreadful concoction fooled Cassiday’s customers. “Few of them,” he noted, “could really tell good liquor from bad.”

Congressmen enjoyed Cassiday’s company and invited him into their drinking club, the Bar Flies Association, which convened in congressional offices for after-hours cocktails. “We would have a few rounds of drinks, sing a few songs and have a general good time,” Cassiday wrote. Congressmen also invited him to play cards in the “poker

room” in the House basement, where pols sat around a mahogany table topped with green felt and played low-stakes stud while waiting for a roll call.

Cassiday loved working in the House. He supported his wife and two children and had fun doing it. “From 1920 to 1925 were the good old days for me, and I like to look back on them,” he wrote. “The House Office Building got so it seemed like home to me.”

But in March 1925, he was busted smuggling booze into the House Office Building while wearing his soon-to-be-infamous green hat. “That forced me to drop a well-established business among members of the House, and start all over again in the Senate Office Building.”

The Senate was less fun. Like many folks rising from the House to the Senate, Cassiday found the upper chamber stodgy: “You find a more general spirit of good fellowship and conviviality in the House.” Senators were more cautious about buying booze from the Man in the Green Hat, so they usually dispatched their secretaries to consummate the transaction.

One senator—Cassiday declined to reveal his name or any others—stored his whiskey in his office bookcase, hidden behind volumes of the Congressional Record. “He never mentioned liquor to me, but occasionally he would say he could use some ‘new reading matter,’ ” Cassiday wrote. “This customer always referred to me as his ‘librarian.’ ”

In the Senate, like the House, Cassiday’s customers came from both parties and both sides of the Prohibition debate. “I served more Republicans than Democrats and more drys than wets, but that was only because the Republicans and the drys have been the overwhelming majority in both branches of Congress.”

Revenue agents in Washington, D.C., hit the jackpot in 1922 when they discovered what was billed as the "largest still in captivity." (Library of Congress)
Revenue agents in Washington, D.C., hit the jackpot in 1922 when they discovered what was billed as the "largest still in captivity." (Library of Congress)

Cassiday’s dry customers explained why they voted to ban booze despite drinking it. “George, I know my district is overwhelmingly dry,” one congressman said. “The people there believe in Prohibition. They can have my vote for all the Prohibition legislation they want, as long as they want it. If the day comes when I get ready to retire from Congress it will be time enough for me to vote the way I drink.”

Basking in his customers’ hypocrisy, Cassiday enjoyed watching congressional debates on Prohibition. “I have sat in the gallery and heard one of my customers deliver a rattling good Prohibition speech. On other occasions, I have heard members of the House and Senate making strong arguments that Prohibition was being well enforced, when I knew good stuff was being regularly delivered to their offices.”

By the fall of 1929, Cassiday had been delivering “good stuff” to Senators for four years. But Vice President Charles Curtis, a passionate Prohibitionist, learned of his activities and called James Doran, head of the Prohibition Bureau. The two hatched a plan to station a spy in the Senate to catch Cassiday. The spy was stupendously inept, but not too inept to catch a bootlegger operating as openly as Cassiday.

His name was Roger Butts, a 20-year-old accounting student with no experience in law enforcement when the Prohibition Bureau sent him to spy on the Senate in December 1929. “I went to work as an employee in the Senate stationery room, where Vice President Curtis had arranged in advance to place me,” Butts wrote in a five-part series of articles for the Washington Post in 1930, a few weeks after Cassiday’s six-part series ran. The stationery room was where senators requisitioned office supplies. It was also where Cassiday made phone calls to his customers. “My instructions from the Bureau were to watch him closely and try to trap him into a sale at the Senate Office Building.”

Butts worked quietly for a couple of weeks, then started sleuthing. “Do you know this fellow the newspapers call The Man in the Green Hat?” he asked a fellow clerk. “I certainly do,” the clerk replied. “He is up here every day doing business.”

Butts told the clerk he wanted to “make a little whoopee” on New Year’s Eve and asked to meet Cassiday. Two days later, the clerk introduced Butts to the bootlegger, who agreed to sell him a bottle of gin for $3. But Cassiday seemed suspicious and he delivered the gin to the other clerk, not to Butts. So the rookie spy’s first attempt to catch Cassiday failed.

Butts tried again a few weeks later. He called Cassiday and summoned him to the stationery room. When Cassiday arrived, Butts introduced him to an undercover Prohibition agent who wanted to buy a bottle of gin. Cassiday asked the question he always asked new customers: Who do you work for? The agent said he was a temporary employee in the House Office Building. Cassiday asked simple questions about the House that the agent couldn’t answer. “Cassiday knew the House Office Building better than the agent did,” Butts wrote. “He seemed mighty uneasy.”

Cassiday took the agent’s $3 and said he’d leave the gin in a nearby storeroom. But when the agent went to get it, he found that Cassiday had left the $3 instead. “We knew then,” Butts wrote, “that Cassiday had got wise.” So Butts’ second attempt failed. Worse, his co-workers guessed that he was a cop, and Cassiday stopped coming to the stationery room.

Butts decided that he needed to convince Cassiday that he was a hard-drinking party animal, not a Prohibition agent. He devised a clever plan: He would come to work drunk. Surely, that would impress Cassiday.

Butts bought a bottle of gin from another bootlegger, stepped into a stairway in the Senate Office Building and took a few swigs. Reeking of gin, he sauntered unsteadily into the station­ery room. “I sat at my desk and started singing and making all kinds of noises to give the impression that I was feeling good.” At first his colleagues were amused, but when Butts’ singing got louder, a co-worker escorted him home to sober up.

Just as Butts hoped, word of his drunkenness reached Cassiday, but the bootlegger did not conclude that he wanted to sell booze to a 20-year-old knucklehead who came to work soused. “He was too shrewd to be taken in,” Butts wrote. “He continued to stay away from me.”

His nutty scheme foiled, Butts finally did what he should have done first: He got a Senate staffer to call Cassiday and ask him to deliver six bottles of gin to a car parked outside the office building. When Cassiday arrived, on February 18, 1930, two Prohibition agents arrested him and confiscated his little black book.

Convicted of distributing liquor, Cassiday was sentenced to 18 months in prison. While waiting for his appeal to be heard, he wrote about his adventures for the Post. Cassiday’s revelations did not reflect well on Republicans, who controlled Congress, or on dry politicians, who seemed like hypocrites. Hoping to curtail the political damage, Vice President Curtis, a very dry Republican, announced that he was the man who had devised the plan to catch Cassiday. Across the country, newspapers mocked Curtis and Congress. “The fantastic no longer seems to be fantastic,” noted the Chicago Tribune. “Actually it does not seem strange that the legislative branch of government should require special effort from the executive to modify its violation of the laws it makes.”

Some senators denounced Curtis for spying on them. Others demanded release of the names in the black book. “I hope to have this list made public,” said Senator Thaddeus Caraway of Arkansas. “As everyone knows, I am one member of the Senate who never took a drink of whiskey in my life.” Caraway didn’t get his wish. Neither the black book nor its contents have ever been revealed and are believed to have been destroyed.

Now famous as “the dry spy,” Butts decided that he, too, should tell his story in the Post: “The public is entitled to know the facts of what I saw and did there.”

Amid this amusing brouhaha, Cassiday’s appeal was denied, and he began serving his 18-month prison sentence. Sort of.

“He never spent a night in jail,” says Frederick Cassiday, son of the Man in The Green Hat. “He’d get up in the morning and put on his suit and drive to the jail and he’d leave before dark and go home.” This part-time incarceration was highly unusual, but so were the bootlegger’s connections. “He had high contacts who would make a phone call to the warden,” his son says.

Fred Cassiday can’t remember his father’s bootlegging days. Born in 1948, he’s a child of his father’s second marriage, to a woman 24 years younger. When Fred was a boy, his dad worked in a shoe factory. By the time he was in high school, his father was retired.

“When I was a teenager, he was this old guy who sat around in his T-shirt and boxer shorts and drank beer,” Fred recalled in a recent interview. The old man told stories about selling booze to senators but he also told stories about wrestling bears in West Virginia. “I looked at him back then as an old bullshitter who was good at spinning yarns, and I didn’t pay much attention.”

The Man in the Green Hat died in 1967, but his legend is periodically revived, usually by people selling booze. In the 1970s a bar opened on Capitol Hill called The Man in the Green Hat. And in 2012 a Washington distillery began selling gourmet hooch called Green Hat Gin. “My father would have loved it,” says Fred Cassiday.

Retired after a career in the Air Force Reserves, Fred Cassiday, 66, now spends his time crusading against a different kind of prohibition. Active in the National Organization for the Reform of Marijuana Laws, he recently testified in the Virginia legislature against the prohibition of pot. “I’m kind of following in my dad’s footsteps,” he said. “I think he’d be proud of me.” n

Peter Carlson writes American History’s Encounter column. He is a former reporter for the Washington Post.