Legs Diamond, born July 10, 1897, killed December 18, 1931, was a gangster, mobster, prohibition-era bootlegger, and Hudson Valley celebrity. He was said to have lived a charmed life, with more than his share of lead flying at him and in him, but he always bounced back. He stood trial many times for many crimes that mostly ended in acquittals. His ability to survive multiple assassination attempts earned him the nickname “clay pigeon” of the underworld. Bootlegging rival Dutch Schultz said about him, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”
Please understand me; this guy was not nice; he was a double-crossing ruthless maniac who had no qualms about killing a friend, foe, bystander, or witness. However, this guy was a celebrated hood in the Hudson Valley for a while.
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As mentioned earlier, in his career as a gangster, Legs Diamond dodged or survived several assassination attempts and trials. Here are a few that this slippery fellow dodged:
- On October 24, 1924, Diamond was shot and wounded by shotgun pellets, reportedly after trying to hijack liquor trucks belonging to a rival crime syndicate.
- October 16, 1927, Diamond tried to stop the murder of “Little Augie” Orgen. Diamond’s brother Eddie was Orgen’s bodyguard, but Diamond substituted for Eddie that day. As Orgen and Diamond were walking down a street on Manhattan’s Lower East Side, three young men approached them and started shooting. Orgen was fatally wounded, and Diamond was shot twice below the heart.
- October 12, 1930, Diamond was shot and wounded at the Hotel Monticello on Manhattan’s West Side. Two men forced their way into Diamond’s room and shot him five times. Still in his pajamas, Diamond staggered into the hallway and collapsed.
- On April 21, 1931, Diamond was arrested in Catskill on assault charges for the beating of a truck driver in 1930. Two days later, he was released from the county jail on $25,000 bond. Five days later, Diamond was again shot and wounded at the Aratoga Inn, a roadhouse near Cairo. After eating in the dining room with three companions, Diamond was shot three times and collapsed by the front door. A resident drove Diamond to a hospital in Albany, where he eventually recovered.
- In August 1931, Diamond and Paul Quattrocchi were tried for bootlegging. The same month, Diamond was convicted and sentenced to four years in state prison. In September 1931, Diamond appealed his conviction. The case was retried in December 1931 in Troy, and Legs was acquitted.
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Jack “Legs” Diamond, named for his dancing ability or ability to run from trouble, often found himself in trouble with other gangs and bootleggers in his home turf of Manhattan, making enemies with dangerous individuals like Dutch Schultz. He also stood trial for a variety of crimes, including murder and kidnapping. Pressure from rival factions and the law forced him to leave Manhattan, and in 1930, he moved to Acra, NY, in the Hudson Valley.
He established a large-scale bootlegging operation in Catskill, NY. The illegal booze produced by his operation was stored in Kingston, NY, at 104 Smith Ave, the site of a warehouse and the former Kingston Barrel Factory building, home to the Kingston Barrel Corp. and an accessory garage building.
By 1930, Legs Diamond was a well-known figure in the Hudson Valley. He attended exclusive events and dinners and was often seen in the area’s best night spots and eateries. He was a supplier of alcohol, which was in high demand. He was perceived as an ordinary man fighting against the government’s unpopular Prohibition.
Legs Diamond distributed large sums of money throughout the Hudson Valley in stores, clubs, hotels and anywhere that would help to endear him to the local populace. His Catskill bootlegging operation and Kingston storage and transport facility employed hundreds of people during the height of the Great Depression. It’s easy to see why he was well-liked and well-protected by the local community, as he provided jobs, money, and booze when they were scarce and sought after. Local law enforcement did not seem to be a problem for Legs. His operations were large and in public view. He lived the high life in public view and without an alias. Yet, he did not seem to be the target of local police.
However, even though he was treated like a celebrity, he still had enemies, and despite his efforts to put some distance between himself and them, he was still within reach and still a juicy target.
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How it all ends
On December 18, 1931, Legs Diamond’s enemies finally caught up with him in Albany, NY. Diamond was staying in a rooming house on Dove Street in Albany while on trial for kidnapping in Troy. On the night of his acquittal, on December 17, Diamond, his family and friends visited a restaurant in Albany and then celebrated at the Kenmore Hotel in Albany.
At 4:30 a.m., Diamond drunkenly went back to the rooming house at 67 Dove Street in Albany and passed out on his bed. Two gunmen entered his room around an hour later. One man held Diamond down, and the other shot him three times in the back of the head.
So who ordered the hit? That’s still an unanswered question. Some say rival and arch-enemy Dutch Schultz finally caught up with Legs Diamond. Other opinions point the finger at the O’Connell political machine in Albany who were trying to keep their monopoly on vice. Yet another opinion is that rival mob leaders wanted to move in on his operation.
On July 1, 1933, Alice Kenny Diamond (age 33), Diamond’s widow, was found shot to death in her Brooklyn apartment. It was speculated that she was shot by Diamond’s enemies to keep her quiet.
And so ended the life and career of Legs Diamond, a criminal and Hudson Valley celebrity.
The Sojourner
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