Jack “Legs” Diamond was shot and seriously injured so many times that he was called “The Gangster Who Couldn’t Be Killed”.

Diamond, born July 10, 1897, to parents from Kilrush, County Clare in Ireland, spent the first years of his life in Philadelphia. After his mother died of a viral infection when Diamond was thirteen, he and his younger brother Eddie joined a group of thugs called “The Boiler Gang.” Diamond was arrested more than a dozen times for various robberies and mayhem, and after spending a few months in a juvenile hall, Diamond was drafted into the military. Army life did not follow Diamond very well. He served less than a year and then decided to be absent without permission. He was soon captured and sentenced to between three and five years at the Federal Penitentiary at Fort Leavenworth, Kansas.

Diamond got out of jail in 1921 and decided that New York City was the place where he could make his fortune. Diamond and his brother Eddie moved to the Lower East Side of Manhattan, where they teamed up with a promising gangster named Lucky Luciano. Diamond did various jobs for Luciano, including small smuggling, along with Brooklyn thug Vannie Higgins. Diamond’s marriage to Florance Williams lasted only a few months (he was never home). But his luck changed when Luciano introduced Diamond to Arnold “The Brain” Rothstein, a notorious gambler and financial wizard. This was the opportunity that Diamond was waiting for and he made the most of it.

After starting out as Rothstein’s bodyguard, Rothstein brought Diamond in as a partner in his lucrative heroin business. When his pockets were filled with enough cash and his need for Rothstein diminished, Diamond, in concert with his brother Eddie, decided to branch out on his own. They thought they could make a package by hijacking the smuggling trucks of other mobsters, including those of Owney Madden and Big Bill Dwyer. This was not a very good idea, as Madden and Dwyer were part of a larger syndicate of criminals, which included Luciano, Dutch Schultz, and Meyer Lansky. Before long, Diamond became a persona non grata in the gangster world and a free prize for anyone who wanted to get rid of him.

In October 1924, Diamond was driving a Dodge sedan down Fifth Avenue, when on 110th Street, a black limousine pulled up next to him. A shotgun fired at Diamond from the back window of the limo, but Diamond was too fast to be killed. He crouched down and stepped on the gas, not looking where he was going. Fortunately, he was able to escape his shooters and drive to the nearby Mount Sinai Hospital. Doctors removed pellets from his head, face, and feet, and when the cops arrived to question him, Diamond was silly.

“I don’t know anything about it,” Diamond told Fuzz. “Why would anyone want to shoot me? They must have found the wrong guy.”

Soon Diamond befriended a gangster who was not looking to kill him. His name was “Little Augie” Orgen. Orgen installed Diamond as his main bodyguard. In return, Orgen gave Diamond a good chunk of his smuggling and narcotics business. This friendship went well, until October 15, 1927, when Louis Lepke and Gurrah Shapiro shot Orgen at the corner of Norfolk and Delancey Street, with Diamond supposedly guarding Orgen’s safety. Diamond was shot in the arms and legs (probably by accident), requiring another trip to the hospital. Upon his release, he became nice to Lepke and Shapiro, and as a result, the two assassins gave Diamond Orgen the smuggling and narcotics deals, as a reward for being stupid enough to get in the way of the bullets destined for Orgen. .

Now Diamond was on top of the world. He had a lot of cash to throw away and became a mainstay in all the best nightclubs in New York City, usually with showgirl Kiki Roberts on his arm, even though he was still married to his second wife Alice Kenny. Diamond was regularly seen at the Cotton Club, The Fay, and the Stork Club, and his photo appeared frequently in the newspapers, depicting Diamond not as a gangster, but as a handsome city man. Soon Diamond was co-owner of the Hotsy Totsy Club on Broadway between 54th and 55th streets, with Hymie Cohen as partner at the helm. The Hotsy Totsy Club had a back room where Diamond frequently settled business disputes, usually shooting his opponents and then carrying them out like they were drunk.

Diamond’s downfall began when on July 13, 1929, three rebellious longshoremen charged in and started a rampage at the bar at the Hotsy Totsy Club. Diamond intervened, with his gang member Charles Entratta, to prevent his manager from being strangled. “I’m Jack Diamond and I run this place,” Diamond told the dock workers. “If you don’t calm down, I’ll blow your head off.”

Talking didn’t work and the shooting soon began. When the smoke cleared, two dock workers were dead and one injured. As a result, Diamond and Entratta took him on the run. While in hiding, Diamond decided that before he could get back to what he was doing, the waiter and three witnesses had to be killed. And soon they were. Cohen was also found dead, and the girl in the hat, the cashier, and a waiter disappeared from the face of the earth. Diamond and Entratta, with everyone who might harm them, quietly surrendered to the police and said, “I heard they were looking for us for questioning.” No charges were ever brought against them, but Diamond realized that New York City was no longer safe for him, so he closed the Hotsy Totsy Club and moved to Greene County in upstate New York.

From upstate New York, Diamond ran a small smuggling operation. But after a few months of impatience, he sent a message to New York City gangsters, namely Dutch Schultz and Owney Madden, who had collected Diamond’s rackets in his absence, that he would return to retrieve what was his. . This put a target right on Diamond’s back, and he became known as the “clay pigeon from the underworld”.

Diamond was sitting in the bar of the Aratoga Inn near Arca, New York, when three men dressed as duck hunters entered the bar and filled Diamond with bullets. Doctors gave him little chance of survival, but four weeks later, Diamond came out of the hospital and told reporters, “Well, I did it again. No one can kill Jack Legs Diamond.”

A few months later, as Diamond was leaving an inn on the upstate highway, he was shot four times; on his back, leg, lung, and liver, but again, he beat the odds the doctors gave him and survived. He was not so lucky in December 1931, when after a night of heavy drinking at the Kenmore Hotel in Albany, he staggered drunk back to his nearby room and fell asleep. The landlady later said she heard Diamond beg for her life, before hearing three shots. Apparently, two gunmen had broken into Diamond’s room, and while one was holding him by both ears, the other was putting three bullets into his brain.

The killers escaped in a red Packard, ending the myth that Jack “Legs” Diamond was the gangster who couldn’t be killed.