The Greatest Gang of Criminals

Arlington never gave rise to an Al Capone or a Nucky Thompson, but it was teeming with bootleggers during Prohibition.
Prohibition Opener

Bootleggers during Prohibition. Library of Congress.

Venture into Rosslyn or Pentagon City today and you’ll find plenty of fashionable watering holes among the luxury high-rises, shopping districts and office complexes. But our urban villages along the Potomac weren’t always that way.

From the 1880s to the turn of the 20th century, the neighborhoods at the foot of the 14th Street Bridge and Key Bridge were seedy, red-light districts where certain Washingtonians came to behave badly. The many gambling halls, brothels and illegal saloons tucked among the stockyards and lumber yards earned Arlington a tongue-in-cheek nickname as the “Monte Carlo of Virginia.”

Booze was always one of the major attractions, and the Arlington Brewing Co. kept the taps flowing at local taverns. Built with masonry from local brickyards, the imposing building manufactured light and dark lagers, ale and porter.

Back then, Virginia’s “blue laws” closed businesses on Sundays, but Jackson City (the riverfront area that is now home to Long Bridge Park) and Rosslyn, with their preponderance of “Sunday saloons,” became major destinations for Sunday drinkers. The front doors and windows of these clandestine bars were dutifully closed on the Lord’s Day, but the back doors were always open.


Eliza Sorrel’s Sunday Bar was one of Rosslyn’s many saloons closed by Commonwealth’s Attorney Crandal Mackey (standing on the porch) in 1904. Arlington Public Library photo.

That party ended in May 1904, when raids led by crusading Virginia Commonwealth’s Attorney Crandal Mackey shut down the Sunday saloons, along with nearby bordellos and casinos. Mackey’s mission would eventually dovetail with efforts by the Women’s Christian Temperance Union and the Anti-Saloon League to precipitate Virginia’s statewide ban on alcohol, which came as the result of a public referendum in November 1916.

With the state’s move to “dry” territory, the Robert Portner Brewing Co. (aka the Tivoli Brewery) in Old Town Alexandria—a spot now occupied by the Trader Joe’s on Washington Street—closed immediately. So did 38 saloons in Alexandria and 47 saloons in Arlington. The Arlington Brewing Co. continued to produce beer for out-of-state sales until production was banned in 1918, after which it began manufacturing Cherry Smash, a nonalcoholic soft drink.


Arlington Brewing Co. was a major supplier to local saloons before Prohibition. Library of Congress photo.

But these shutdowns, however symbolic, didn’t do much to curtail the flow of liquor in Arlington. If anything, they heightened the public’s taste for the hard stuff. Hundreds of citizens hid makeshift stills in their homes (made with parts from the local hardware store), producing rye whisky and bathtub gin for personal consumption. And as demand for contraband grew, many home distillers began to launch small-time bootlegging operations.

Most of Virginia was still rural in the early 20th century, peppered with small towns where evangelicals cast their eyes askance at “Demon Rum.” But Northern Virginia’s culture, by nature of its proximity to the nation’s capital, was more progressive.

Alexandria County took the name “Arlington” in 1920—coincidentally the year that national Prohibition began—as a way of asserting its own identity from the city to its south. Over the next decade, Arlington grew 66 percent (from 16,040 residents in 1920 to 26,615 in 1930) as neighborhoods such as Clarendon grew up along streetcar lines.

“The 1920s and 1930s were an era when Arlington was beginning the transition from a rural county into an urban environment,” says Karl VanNewkirk, a docent at the Arlington Historical Society.

During this time, Sheriff Howard Fields was charged with keeping the peace and patrolling against the growing tide of Prohibition violators. In 1924, he created a vice squad to deal with liquor-related offenses. Its first arrests were six men near East Falls Church—three black and three white—who had formed an amateur bootlegging operation. They were charged with alcohol possession and gambling.

From that point forward, arrests continued at a steady pace. In October 1925, an Arlington grand jury issued indictments in 57 cases. This constituted the largest number of criminal proceedings the county had ever witnessed in a single month, and almost all were “dry” law offenses.


In November 1923, a federal judge ordered that 18,000 bottles of beer, intercepted en route from D.C. to Philadelphia, be dumped. The bottles are now buried beneath the Pentagon.

This trend wasn’t wholly attributed to an uptick in illicit activity. For each citizen convicted, the arresting officer and prosecutor on the case received compensation of $10, per state law. Corruption ensued as incentivized agents became overzealous in their arrests. In 1926, the Virginia legislature voted to eliminate bounties for prosecutors when their defendants pleaded guilty, and to award only $5 per conviction. The reward for arresting officers was reduced to $1.50.

In addition to harboring plenty of small-time moonshine operations, Arlington became a major thoroughfare during Prohibition. Making frequent use of arterial roads such as Lee Highway and Columbia Pike, rum runners smuggled an estimated 22,000 gallons of booze into D.C. every week to supply thirsty congressmen and the lobbyists and journalists who hobnobbed with them on “Rum Row,” a stretch of speakeasies along the north side of E Street downtown, just east of 14th Street. (Not coincidentally, the local bureaus of more than 30 newspapers were established just around the corner from Rum Row at the site that is now the National Press Club.)

Although much of D.C.’s illegal liquor came from Baltimore, bootleggers also blazed well-traversed routes across three of the bridges linking Arlington to the District: the Key Bridge (completed in 1923 to replace the aging Aqueduct Bridge), the 14th Street Bridge and the Chain Bridge. The growing popularity of the automobile (this was the era of Ford’s Model T)made it fairly easy for liquor dealers to move their products to market.

For shipments trucked in from points south, Arlington was a pivotal way station in the supply chain. It was the stopping point where large quantities of alcohol were broken into smaller loads to be placed in fast cars that could zip across the river unnoticed. Some cars employed smoke-screen devices that could be switched on if and when their drivers were being chased by the police.

The engineer drivers of these speedy delivery vehicles (who, it should be noted, went on to form NASCAR) often made their runs en masse, deploying multiple cars simultaneously in order to confuse and evade the authorities. Such was the case in one high-speed chase on May 4, 1923. As police in Rosslyn apprehended one of five booze-filled cars headed for the District, the others sped off, leaking trails of liquor in their wake—the result of bullets fired by Prohibition agents.

Sometimes the bullets exchanged in gunfights hit more than barrels of gin. On February 12, 1930, officer Raymond Crack was struck in the face by a bootlegger’s bullet while chasing a convertible that had come screaming across the Key Bridge, loaded up with 17 cases of liquor. Crack survived; he was treated while fellow police continued the chase to Occoquan. There, the bootleggers finally abandoned the vehicle and fled into the woods. Both men were ultimately arrested and served time in jail.

By the late 1920s, the public began to realize that the so-called “Noble Experiment” wasn’t working. Arlington’s jail was overcrowded with dry law offenders, and citizens were tiring of what they perceived as heavy-handed law enforcement that infringed on their personal liberties.

Public disenchantment was palpable at one political debate hosted at Washington-Lee High School in October 1928, during which Republican U.S. District Attorney Leo Rover proclaimed: “The prohibition law is being enforced in Washington and Arlington County. Ask the people of this county if it isn’t.”

When his statement was met by jeers, he retorted, “If it is not, it is because the people do not want it enforced.”


Wilson Boulevard was a well-traveled route for bootleggers in the 1920s. Arlington Public Library photo.

Other signs of Prohibition’s unraveling were soon to follow. Among the most notable was former Commonwealth’s Attorney Crandal Mackey’s run for U.S. Congress in 1930, during which he revised his staunch position on Prohibition. Calling for a repeal of the 18th Amendment, he suggested that federal oversight be replaced by statewide control of liquor. (He lost the Democratic primary to Howard Smith, who represented Arlington until 1967.)

Shortly thereafter, a store owned and operated by Mackey’s son Darlington was raided near Chain Bridge in 1931. Mackey leapt to his son’s defense, claiming that agents had conducted the raid without a warrant and that the man who sold them liquor was not an employee. “I am confident that my son does not sell liquor there, and I shall defend him to the utmost,” Mackey said in a statement. This didn’t seem to help. Darlington was released on bond but indicted by a grand jury.

As the “wet” cause ascended and Democratic and Republican candidates considered adopting wet planks to their platforms for the 1932 presidential election, the Women’s Christian Temperance Union dug in its heels. In April of that year, leaders of the organization’s Alexandria City–Arlington chapter held a meeting at the Clarendon Methodist Church, during which they advised local women to boycott the polls rather than vote for a party that supported repeal. The once-powerful group was in denial as its influence slipped away.

Weeks later, Sarah Lee Fain, one of the first two women elected to the Virginia legislature, addressed Arlington Democrats at the Arlington County Courthouse and lambasted the 18th Amendment. “I am not for whiskey. I am against it,” she said. “But I have been conclusively shown that the use cannot be prohibited and the only way to control it is to handle it legally through government dispensaries.”

“I am a defender of Prohibition,” Fain continued. “I thought it would bring about temperance. It won’t. It has given birth to the greatest gang of criminals this country has known.”

Citizens tended to agree, although in their view the greatest offenders were elected officials. Voters were especially soured by a Congress that continued to drink under the table, all the while funding Prohibition enforcement. When Washington’s infamous congressional bootlegger George Cassiday (aka “the Man in the Green Hat”) spilled the beans in 1930 to The Washington Post, he estimated that four out of five congressmen and senators were drinkers.

It wasn’t hypocrisy, but rather economics that ultimately ended the nation’s ban on alcohol. With the onset of the Great Depression, the country desperately needed the jobs and taxes from liquor. President Franklin D. Roosevelt and a wet Democratic Congress were elected on the promise of repeal, and the 21st Amendment was dispatched to the states for ratification. Prohibition ended on December 5, 1933.

On the matter of regulating the legalized distribution of booze, Delegate Fain and candidate Mackey proved prescient. Virginia adopted state control over distilled spirits and maintains that authority to this day.

Arlington has only six state-run ABC stores that sell liquor to the county’s 208,000 residents—which explains why some Arlingtonians still race across the bridges to buy their spirits in D.C., where they say the selection is broader and the prices are sometimes better. They might get a speeding ticket along the way, but not jail time.

Arlington resident Garrett Peck is the author of Prohibition in Washington, D.C.: How Dry We Weren’t, and The Prohibition Hangover: Alcohol in America from Demon Rum to Cult Cabernet. He also leads the Temperance Tour of Prohibition-related sites in D.C.

Bottoms Up

Want to party like it’s 1929? Have your guests enter through the back door and serve these oldies but goodies.

The Rickey
Created in the 1880s in honor of Col. Joseph Rickey, the Democratic lobbyist who owned the legendary Shoomaker’s bar in D.C., the “Rickey” was nicknamed “air conditioning in a glass”—a perfect antidote to Washington’s sultry summers.

1.5 oz. gin or whiskey
Juice of ½ lime
Club soda

Add gin or whiskey to a highball glass. Squeeze in the lime juice, then drop in the lime shell. Add ice, top with club soda and give it a quick stir.

Virginian Whiskey Punch
If Virginia has a native spirit, it is whiskey. Although it was originally made with rye in George Washington’s day, distillers later switched to corn (moonshine is un-aged corn whiskey). This cocktail is a nice balance of sweet and sour.

1 oz. simple syrup (add two parts sugar to one part boiling water; stir until the sugar dissolves, then cool)
Juice of ½ lemon
1 ½ oz. rye whiskey or bourbon

Fill a highball glass or goblet one-third full of crushed ice. Lightly dust the top with sugar. Add simple syrup and stir hard. Add lemon juice, more ice and whiskey. Stir and stir, gradually adding more crushed ice until the glass is filled to the top and the outside is frosty.

Recipes from Prohibition in Washington, D.C.: How Dry We Weren’t.


Categories: Local History