Bootlegging Was a Big Business in the Hudson Valley During Prohibition

The Peter Barmann Brewery | Photos courtesy of Friends of Historic Kingston

When Prohibition began in January 1920, bootlegger and gangster Legs Diamond made a name for himself in the Hudson Valley.

One hundred and one years ago, the Prohibition had begun: The 18 Amendment to the U.S. Constitution took effect on January 17, 1920, banning “the manufacture, sale, or transportation of intoxicating liquors” throughout the land. The effect of the new laws on the Hudson Valley, a brewing hub almost from the day Europeans set foot on its shores, was devastating.

Countless breweries in the region were put out of business, including one in Kingston once owned by Peter Barmann, which had been supplying suds since 1852. Before its demise, however, it was the locus of operations for the infamous gangster Jack “Legs” Diamond.

The Peter Barmann Brewery sat at the corner of what is now Barmann Avenue and South Clinton Avenue in Kingston. Diamond was primarily a bootlegger, and the Feds had long suspected that his product flowed to New York City and Albany from somewhere around Kingston. For years, they tried and failed to find the tap.

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The Peter Barmann Brewery
The Peter Barmann Brewery | Photos courtesy of Friends of Historic Kingston

But on May 1, 1931, they succeeded. Diamond had just been shot—for the fourth time—in a speakeasy in Acra (Greene County) and was recuperating in an Albany hospital. Seizing the opportunity, enforcement agents raided two warehouses on Bruyn Avenue. They arrested 10 men and hauled off some 3,000 barrels and 41,000 bottles of ale, worth over $200,000 in Depression-era money—the equivalent of nearly $3.6 million today.

A month after the raid, an elite troop of agents called “the Flying Squadron” was dispatched to the region to dig deeper. On June 2, they conducted a stake out at the Barmann Brewery and witnessed a truck leave the premises. One agent commandeered the truck and captured its driver. Two other agents, brandishing Thompson machine guns—“Tommy guns”—took the brewery. They discovered so much illicit beer, brewing equipment, trucks, weapons and cash that it came to be called the “million-dollar seizure,” one of the biggest Prohibition raids ever.

legs diamond, prohibition
Photo by Wikimedia Commons

It also revealed Diamond’s secrets. The Feds found that local plumbers, on the take from Diamond, had snaked a half-mile long rubber hose through tunnels they had dug under the brewery, into the city sewer lines and finally to those warehouses on Bruyn Avenue. That effectively moved his shipping department far from the manufacturing plant, which helped keep Diamond’s operations, literally, underground.

Related: Legs Diamond: A History of Kingston’s Most Notorious Gangster

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