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

Eighty years ago, a raid on a Kingston bootlegging operation helped bring down notorious gangster Legs Diamond

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The “million dollar” raid

Prohibition began on January 20, 1920, killing off thousands of successful breweries around the country. One of those was the Peter Barmann Brewery. Located on the corner of what is now Barmann Avenue and South Clinton Avenue in Kingston, the beer maker had been in operation since 1852. Before it died, though, the Barmann Brewery was in the illicit hands of Legs Diamond. 

“Do you know what Legs Diamond was trying to do?” an associate of his asked during an interview. “Well, he was trying to control all the illicit activities in the East. He was trying to be as big as Capone.”
— from Jack “Legs” Diamond: Anatomy of a Gangster, by Gary Levine

The feds knew that beer was flowing to New York and Albany from Kingston, but couldn’t find the source. On May 1, 1931, while Diamond was hospitalized in Albany after his fourth shooting (which took place in a speakeasy in Acra, Greene County), local agents hit two warehouses on Bruyn Avenue. According to Levine’s account of the raid, they nabbed 10 men and about 3,000 barrels and 41,000 bottles of ale, worth more than $200,000. Three elite federal agents, known as “the Flying Squadron,” were then assigned to the area; on June 2, while hiding in the grass near the brewery, they saw a truck leave the yard. One agent jumped on the truck and forced the driver, Diamond associate John Sheehan, to surrender. The other two agents, armed with Thompson machine guns, stormed the brewery. They found so much cash, weaponry, brewing equipment, trucking equipment, and beer that the raid became known as the “million dollar seizure.” It was one of the biggest such raids of the time.

The agents also discovered how the operation had escaped their attention for so long. Underneath the brewery, local plumbers on Diamond’s payroll had run a flexible, two-and-a-half-inch rubber hose through the city sewer lines to the Bruyn Avenue warehouses a half-mile away. The beer was made at the brewery, then transported to the warehouse, bottled, and distributed far from the prying eyes of the law. City of Kingston historian Ed Ford says his late brother-in-law, a plumber, actually worked in that area and found some remnants of the pipes and hoses. “I wish he had saved some for me,” Ford says. He has visited the tunnels himself but never discovered any artifacts. There were also rumors that victims of Diamond’s violence — including New York City’s famed Judge Crater, who mysteriously disappeared in 1930 — were dumped in the caves and tunnels under the brewery. “I never saw any bodies either,” Ford notes.


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