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Jack 'Legs' Diamond: Newspaper clipping following his arrest for torturing and kidnapping

Infamous Irish American bootlegger, Jack “Legs” Diamond, celebrated as hero

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Jack 'Legs' Diamond: Newspaper clipping following his arrest for torturing and kidnapping

In the small town of Cairo, New York bootleggers, including infamous Irish American gangster Jack "Legs" Diamond, are being celebrated.

According to local reports Diamond one of the most popular of the bootleggers and tales of his crimes and adventures have become stuff of legend. This month he’ll be on of the many bootleggers being honor in the brand news prohibition-era speakeasy in the Cairo, a village with a population of 1,500.

Diamond was born in Philadelphia to Irish parents. His real name was Jack Moran. He was also known to the public as Gentleman Jack. Diamond became the stuff of legend because he survived for so long. He lived on the run and was shot on numerous occasions.

His mother died when he was just 16 and he moved to New York with his father, John. He soon joined a street gang called the Hudson Dusters. His first arrest was in 1914 for burglary and the arrests continued throughout his life. Diamond served in the U.S. Army during World War I but deserted in 1918 and 1919 and was convicted for desertion.

Upon his release from jail he was hired as an assassin by Jacob Orgen, aka Little Augie. He became the bosses personal bodyguard and was shot twice during an attempted assassination of Orgen.

Diamond got his nickname “Legs” because of his flamboyant lifestyle, his wonderful dancing and his womanizing ways. He was a celebrity in Upstate New York where he ran his bootlegging business.

He sold alcohol to downtown Manhattan but this meant he came into conflict with other gangsters like Dutch Schultz and other gangs throughout the city. When Diamond failed to make a payment to one of the gangsters he was shot five times at the Hotel Monticello while he was having dinner.

Diamond moved to Upstate New York hoping to avoid further conflict but this was not to be.

In 1930 Diamond and his men kidnapped a truck driver demanding to know what alcohol he was  transporting. He refused to tell and they beat and tortured him. A few months later they also kidnapped a man called James Duncan. He was eventually charged with four years in prison but never served the time, he died one day after his sentencing. 

The area of Green County was ideal for Diamond’s needs; to keep away from prying eyes and one step ahead of his enemies. According to Sylvia Hasenkopf, vice president and secretary of the Cairo Historical Society, the beautiful and quiet area in the Catskills was home to all sorts of alcohol production.

“Greene County was known for the production of hard cider produced from fermented apples…Given the rural nature and remote roads of the county," Hasenkopf told her local newspaper the Daily Mail. "We had all the right ingredients for the illicit manufacture of alcohol during the Prohibition years.”

“Illegal stills popped up everywhere, however, their locations were kept very secret…We have a number of sites right here in Cairo.”

In the mid-1920s Diamond rented a house on Route 23 in Acra. “Being chased, almost continuously, by either the police or fellow gangsters, [Diamond] found the peace and quiet of Greene County an ideal place to set up his bootlegging operations.”

According the local historians Diamond escaped death, one of the many episodes, at a shoot out in the Aratoga Inn on April 27, 1931. Schultz and his men had finally caught up with him.

Then on December 18, 1931 Diamond was shot by his enemies as he lay, passed out, in bed at his Dove Street hideout in Albany. This was the night after he had been charged with four years in prison.

Hasenkopf said “Although [Diamond] was gone, he left an indelible mark on the town of Cairo and his legend lives on.”

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