Jack "Diamond" was shot and wounded so many times, he was called "The Gangster That Can't Be Killed."
Diamond, born July 10, 1897, from parents in Kilush, County Clare, Ireland, spent the first years of his life in Philadelphia. After his mother died of a viral infection when Diamond was thirteen years old, he and his younger brother, Eddie, fell into a group of laborers called "The Boiler Gang." Diamond was arrested more than a dozen times for various robberies and grievous defeats, and after spending several months in a minor reformer, Diamond was drafted into the army. Army life did not fit Diamond well. Served for less than a year, after which he decided to switch to AWOL. He was soon apprehended and sentenced to three to five years at the Federal Penitentiary in Fort Leavenworth, Kansas.
Diamond was released from prison in 1921, and he decided that New York was the place to make his fortune. Diamond and his brother, Eddie, have moved to Manhattan, Lower East Side, where they meet up with an impending gangster named Lucky Luciano. Diamond did various strange tasks for Luciano, including a few boots, in connection with Brooklyn thug Vani Higgins. Diamond's marriage to Florence Williams lasted only a few months (he had never been home). But his luck changed when Luciano introduced Arnold's "Brain" to Rothstein, a notorious gambler and financial wizard. It was the break Diamond was waiting for, and he made the best of it.
After starting out as a Rottstein bodyguard, Rothstein introduced Diamond as a partner in his lucrative heroin business. When his pockets were full of money and his need for Rothstein diminished, Diamond, along with his brother Eddie, decided to split up on their own. They realized they could make a package to kidnap the tow trucks of other mobsters, including those of Owen Madden and Big Duer. This was not a good idea, as Madden and Dwyer were part of a larger syndicate of criminals that included Luciano, Holland Schulz and Mayer Lansky. For the time being, Diamond is a non grata persona in the gangster world and is a free choice for anyone who wants to get rid of him.
In October 1924, Diamond was driving a Dodge sedan up Fifth Avenue when, on 110th Street, a black limousine pulled past him. A shotgun fired at Diamond from the back window of the limo, but Diamond was too fast to be killed. He lowered himself and struck the throttle without looking at where he was going. Fortunately, he managed to escape from his shooters and drive to the nearby Mount Sinai Hospital. Doctors removed pellets in his head, face and legs, and when the cops arrived to question him, Diamond fell.
"I don't know anything about it," Diamond said of things. "Why would anyone want to shoot me? There must be a wrong person."
Soon Diamond befriends a gangster who doesn't want to kill him. His name was Little Augie Orgen. Orgen installs Diamond as his main bodyguard. In return, Orgen gave Diamond a nice share of his drug and drug loading business. This friendship was going well until October 15, 1927, when Luis Lepke and Gura Shapiro shot Orgen at the corner of Norfolk and Delaney Street, as Diamond was allegedly on the alert for Orgen's safety. The diamond was shot in the arms and legs (probably by accident), necessitating another trip to the hospital. After his release, he befriended Lepke and Shapiro, and as a result, the two killers gave Diamond Orgen the bootlegging and drug business as a reward for being stupid enough to thwart bullets aimed at Orgen.
Diamond was at the top of the world now. He had enough money to throw, and he became a mainstay of all the best nightclubs in New York, usually with showman Kiki Roberts on hand, despite the fact that he was still married to his second wife, Alice Kenny. Diamond was seen regularly at the Cotton Club, El Fay and Stork Clubs, and his picture was often found in newspapers that portrayed Diamond not as a gangster but as a handsome man in the city. Soon Diamond was the private owner of Broadway's Hotsy Totsy Club between 54th and 55th Streets, with Hymie Cohen his front partner. The Hotsy Totsy Club had a back room where Diamond often settled business disputes, usually by shooting his opponents to death and then carrying them out as if they were drunk.
The fall of Diamond began when, on July 13, 1929, three unscrupulous dockers loaded up and began to collapse at the Hotsy Totsy Club bar. Diamond jumped inside with his bandmate Charles Entrata to stop his manager from being muted. "I'm Jack Diamond and I run this place," Diamond told the Dockers. "If you do not calm down, I will beat you up."
Talking failed and soon the shooting began. When the smoke cleared, two dockers were dead and one wounded. As a result, Diamond and Entratta took him to the lamb. While they were hiding, Diamond decided that before he could return to do what he was doing, the bartender and three witnesses had to be killed. And soon they were. Cohen was also dead, and the girl checking the hat, cashier and a waiter disappeared from the face of the earth. Diamond and Entra, all who could harm them, calmly turned to the police and said, "I heard we were wanted for questioning." They have never been charged, but Diamond realized that New York was no longer safe for him, so he closed the Hotsy Totsy Club and moved to Green County in New York.
From New York State, Diamond performed a small loading operation. But after a few months of impatience, he sent word back to the gangsters in New York, namely the Dutch Schultz and Owen Madden, who lifted Diamond's rockets in his absence that he was returning to take back what was his. This placed the target precisely on Diamond's back, and he became known as the "clay pigeon of the underworld."
Diamond was sitting at the Aratoga Inn's bar near Arc, New York, when three men dressed as duck hunters climbed into the bar and filled Diamonds with bullets. The doctors gave him a small chance of survival, but four weeks later Diamond came out of the hospital and told the press: "Well, I did it again. No one can kill Jack Legs Diamond. "
A few months later, when Diamond was leaving the roadside inn, he was shot four times; in his back, legs, lungs and liver, but again he beat the chances his 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 boarding house and fell asleep. The landlady then said she heard Diamond pray for his life before hearing three shots. Apparently, two gunmen had slipped into Diamond's room, and while one was holding it to his two ears, the other was inserting three brains into his brain.
The killers fled to Red Packard, ending the myth that Jack "Legs" Diamond is a gangster who can't be killed.