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

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

Wikimedia Commons

This career criminal and rival of infamous bootlegger Dutch Schultz rose to notoriety, made enemies, and met his end in the Hudson Valley.

Legs Diamond, it was said, never met a friend he didn’t double-cross. Even by the dubious standards of Depression-era gangsters, he was no good. His enemies loaded so much lead into him that rival gangster Dutch Schultz once asked his own henchmen, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”

Yet, by 1930, he was also the Hudson Valley’s biggest celebrity, a symbol of the little guy standing up to the heavy government hand of Prohibition. He frequently attended dinner parties and supper clubs throughout the region (including at this rumored-to-be haunted house in Troy). After being forced out of New York City, he set up operations in Catskill. Most of the locals knew he was running booze out of a brewery in Kingston. But government agents charged with enforcing the 18th Amendment could never figure out how.

Raids in the early summer of 1931 finally uncovered the subterranean secret to his operation, and led to the beginning of the end for Legs Diamond. The man who may have gotten his nickname for the way he could run for his life ran out of running room. Five months later, someone finally shot this guy “so he don’t bounce back.”

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Portrait of Diamond’s nemesis, Dutch Schultz | Photo courtesy of Dutch’s Spirits

“A Future in the Catskills”

Jack Diamond was born July 10, 1897, in Philadelphia to Irish immigrant parents. His mother died in 1913, and the family moved to Brooklyn. Quickly becoming a member of a street gang, Diamond’s criminal record began while still a teenager, when he robbed a jewelry store. After being jailed for desertion during World War I, Diamond went to work for big-time gangster Arnold Rothstein, the man who fixed the 1919 World Series. (You may have seen Rothstein depicted on the HBO series Boardwalk Empire by actor Michael Stuhlbarg.) He also freelanced as a hit man for Jacob “Little Augie” Orgen, committing his first murder, and soon after got shot himself when Orgen was killed.

Legs began his own bootlegging business, mostly by hijacking trucks loaded with booze to fuel his speakeasies. He was outgoing and flamboyant, a womanizer (though he was married), and a terrific dancer. In fact, that’s the more likely source of his nickname, according to the late Gary Levine (no relation to me), a former professor at Columbia-Greene Community College in Hudson who published Jack “Legs” Diamond: Anatomy of a Gangster in 1995. He quickly became the target of other gangsters. By the end of the 1920s, New York had become too hot for him. He’d been shot two more times, and he needed a new base of operations.

In Legs, a fictional account of the gangster’s life, author William Kennedy envisions Diamond explaining to his attorney, Marcus, that he’s “got a future in the Catskills.”

“Don’t you think you ought to get straight first?”

“You don’t understand, Marcus. You can carve a whole goddamn empire up there if you do it right. Capone did it in Cicero. Sure there’s lots of roads to cover, but that’s all right. I don’t mind the work. But if I slow now, somebody else covers those roads. And it’s not like I got all the time in the world. The guineas’ll be after me now.”

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“You think they won’t ride up to the Catskills?”

“Sure, but up there I’ll be ready. That’s my ballpark.”

legs diamond
Wikimedia Commons

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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The Albany house where Legs Diamond was murdered | Wikimedia Commons, Photo by Daniel Case

“They’ll Never Get Legs!”

Legs Diamond left the Albany hospital on May 31, 1931, to answer kidnapping charges in Catskill. In front of the courthouse, Gary Levine writes, a nine-year-old boy shouted, “They’ll never get Legs!”

The trial was moved to Troy, and finally held in December. Legs was acquitted — probably by bribing the jurors — and celebrated by getting drunk and visiting his mistress in Albany. In the wee small hours of December 18, he stumbled to his boardinghouse rooms on Dove Street and passed out.

The feds didn’t get Legs. But others did. Two gunmen followed him into the bedroom, where he lay sprawled out in his underwear, fired three bullets into his head at close range, and sped off in a black sedan. No one knows for sure who finally stopped Legs Diamond from bouncing back. He had enemies on both sides of the law. It could have been other gangsters. It may have been the Albany police department, under the direction of political boss Dan O’Connell; O’Connell claimed as much in Kennedy’s book O Albany! As with much of gangster life, and death, much remains mysterious.

“There are so many stories,” says Ed Ford. “How do you know the truth?”

Related: Dutch’s Spirits Bootlegging Distillery Brings Booze Back to Pine Plains

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