Jack "Legs" Diamond was shot and injured so many times, he was called "The Gangster Who Can't Be Killed."
Diamond, born July 10, 1897, a native of Kilrush, Clare County, Ireland, spent the first years of his life in Philadelphia. After his mother died of a viral infection when Thirteen was 13, he and his younger brother Eddie broke into a group of tough people called the "Boiler Gang." Diamond was arrested more than a dozen times for robbery and robbery, and after spending several months in a juvenile detention center, Diamond was taken into the military. Army life didn't exactly match Diamond's. He served less than a year and then decided to go to AWOL. He was soon apprehended and sentenced to three to five years in the Federal Prison at Fort Leavenworth, Kansas.
Diamond was released from prison in 1921, and he decided New York City was where he could make a fortune. Diamond and his brother Eddie have moved to Manhattan to the Lower East Side, where they entered with an oncoming gangster named Lucky Luciano. Diamond did a variety of odd jobs for Luciano, including a little tweaking, along with Brooklyn thug Vannie Higgins. Diamond's marriage to Florance Williams lasted only a few months (he had never been home). But his luck changed, when Luciano introduced Diamond to Arnold "The Brain" Rothstein, a notorious gambler and financial wizard. This was the break Diamond had been waiting for and he did his best.
After starting as a bodyguard for Rothstein, Rothstein brought in Diamond as a partner in his lucrative heroin business. When his pockets became full of money and his need for Rothstein diminished, Diamond, in collaboration with his brother Eddie, decided to set aside the money on his own. They assumed they could make a crowd that robs robberies of other mobsters, including those of Owney Madden and Big Bill Dwyer. This was not a good idea, since Madden and Dwyer were part of a larger crime syndicate, which included Luciano, Dutch Schultz and Meyer Lansky. At no point was Diamond a persona non grata in the gangster world, and it's free to choose who wanted to get rid of him.
In October 1924, Diamond was driving a Dodge sedan along Fifth Avenue when, at 110 Street, a black sedan went past him. The rifle fired at Diamond from the back window of the limo, but Diamond was too fast to be killed. He bent down and hit the gas, not looking where he was going. Fortunately, he was able to escape with his shooters and be taken to nearby Mount Sinai Hospital. Doctors removed the pellets in his head, face and legs, and when officers arrived to examine him, the Diamond went crazy.
"I don't know anything about it," he told Diamond. "Why would anyone want to shoot me? They must have the wrong guy."
Soon Diamond befriended a gangster who did not want to kill him. His name was "Little Augie" Orgen. The Orgen has recruited Diamond as his chief bodyguard. In turn, Orgen gave Diamond a good chunk of his narcotics and narcotics business. That friendship went just fine, until October 15, 1927, when Louis Lepke and Gurrah Shapiro shot Orgen at the corner of Norfolk and Delancey streets, with Diamond allegedly standing guard for Orgen's security. The diamond was shot in the arms and legs (probably by accident), which required another trip to the hospital. After his release, he befriended Lepke and Shapiro, and as a result, the two assassins provided Diamond Orgen with decorating hands and narcotics, as a reward for being stupid enough to find bullets for Orgen.
Now Diamond was at the top of the world. He had enough money to throw, and he became a mainstay in all New York nightclubs, usually with showgirl Kiki Roberts on hand, despite the fact that he is still married to his second wife, Alice Kenny. Diamond was regularly seen at the Cotton Club, El Fay and the Stork Club, and his image often appeared in newspapers, which did not portray Diamond as a gangster, but as a handsome man in town. Soon Diamond was part of the owner of the Hotsy Totsy Club on Broadway between 54th and 55th Streets, with Hymie Cohen as front partner. The Hotsy Totsy Club had a back room where Diamond often settled business disputes, usually by shooting opponents to death and then running them as if they were drunk.
The diamond fall began when, on July 13, 1929, three unlucky doctors boarded and began a ruckus at the Hotsy Totsy Club bar. Diamond stepped in, with gang member Charles Entratta, to prevent his manager from suffocating. "Me and Jack Diamond and I run this place," Diamond told the doctors. "If you do not calm down, I will blow your (lofty) heads."
The conversation failed and soon the shooting began. When the smoke cleared, two doctors were dead and one was injured. As a result, Diamond and Entratta took him on the attack. While hiding, Diamond decided that before he could return to what he was doing, the bartender and three witnesses had to be killed. And soon they were. Cohen also found himself dead, and a hat girl, cashier and one waiter disappeared from the face of the earth. Diamond and Entratta, all out of the way who could harm them, calmly turned to the police and said, "I heard they were asking us for questioning." There was never an indictment 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, upstate New York.
From upper New York, Diamond performed a small boot operation. But after months of impatience, he sent a message to gangsters in New York, more specifically Dutch Schultz and Owney Madden, who had trained Diamond rackets in his absence, to return to retrieve what was his. This set the target straight on Diamond's back, and he became known as the "clay pigeon of the underworld."
Diamond was sitting at a bar in the Aratoga outlet near Arce, New York, when three men dressed in duck hunting burst into a bar and filled with Diamond bullets. The doctors had 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 the guest bypass, he was shot four times; into his back, legs, lungs and liver, but he again beat the chances his doctors gave him and survived. He was not so lucky in December 1931 when, after a night of spirits at the Kenmore Hotel in Albany, he drunkenly retired to a nearby boarding house and fell asleep. The housewife said afterwards that she heard Diamond pray for his life, before she heard three gunshots. Two assailants allegedly broke into Diamond's room, and while one held him by two ears, the other threw three slugs into his brain.
The killers fled in a red Packard, ending the myth that Jack "Legs" Diamond was a gangster who couldn't be killed.