Jack "Feet" The diamond was shot and wounded so many times that he was called "The Gangster Who Didn't Die."
Born on July 10, 1897 in Clarus, Kilrush, Ireland, Diamond, Diamond spent his first years in Philadelphia. After his mother died of a viral infection at the age of thirteen, Diamond and his younger brother, Eddie, fell into a harsh group called "The Deserter." The diamond was arrested more than a dozen times as a result of various abductions and chaos, and after spending a few months in the juvenile Reformation, Diamond was pulled into the army. The life of the army did not suit Diamond well. He earned less than a year, then decided to go AWOL. He was soon arrested and sentenced to three to five years in federal prison in Fort Leavenworth, Kansas.
Diamond was released from prison in 1921 and decided that New York City was the place where he could earn his fortune. Diamond and his brother Eddie moved to the East Side of Manhattan where they fell down with a future gangster named Lucky Luciano. Diamond did a variety of odd jobs for Luciano, including a small boot strap with Brooklyn thug Vannie Higgins. Diamond's marriage to Florance Williams lasted only a few months (he was never home). But his fortune changed when Luciano introduced Diamond to infamous gamer and financial wizard Arnold "Brain" Rothstein. It was the break Diamond expected and he made the best of it.
After taking up Rothstein as a bodyguard, Rothstein introduced Diamond into his lucrative heroin business. When his pockets were full of cash and his need for Rothstein diminished, Diamond decided to pull his brother Eddie on his own. They thought they could make a bundle by hijacking the trunk of other gangsters, including Owney Madden and Big Bill Dwyer. That was not a good idea, as Madden and Dwyer were part of a larger syndicate of criminals, including Luciano, Schultz of the Netherlands and Meyer Lansky. At some point in the Diamond gangster world, there were persona non grata and free collections for anyone who wanted to get rid of him.
In October 1924, Diamond Dodge was driving a sedan off Fifth Avenue when it was struck by a black limousine on 110th Street. A shot was fired from the back of Diamond's limousine, but Diamond was too quick to kill. He plunged down and hit the accelerator, no matter where he was going. Luckily, he managed to escape his shooters and drove himself to the nearby Mount Sinai Hospital. Doctors removed pellets from his head, face and feet, and when police questioned him, Diamond buried his body.
"I don't want that," Diamond said dimly. "Why would anyone want to shoot me? They have to get the wrong man."
He soon became friends with a Diamond gangster who didn't want to kill him. His name was "Little Augie" Orgen. Orgen placed Diamond as his main bodyguard. In return, Orgen gave Diamond a fair share of his boots and drug business. That friendship went brilliantly, until October 15, 1927, when Louis Lepke and Gurrah Shapiro shot Orgen on the corner of Norfolk and Delancey streets, with diamonds allegedly standing for the safety of Org. The diamond was shot in the arms and legs (probably by accident), necessitating another trip to the hospital. When he was released, he did a nice job with Lepke and Shapiro, and as a result, the two killers rewarded Diamond Oren's boots and the drug business for being stupid enough to go the way of Orgen's bullets.
Now Diamond was at the top of the world. He had a lot of money to throw around and became a support service in all New York City top clubs, usually with showgirl Kiki Roberts on hand, despite still being married to his other wife, Alice Kenny. Diamond was regularly seen at the Cotton Club, El Fay & Stork Club, and was often featured in newspapers where Diamond was portrayed not as a gangster, but as a handsome city man. He soon became a co-owner of the Hotsy Totsy Club, located between 54th and 55th Streets of Diamond Broadway. Hymie Cohen was her partner. The Hotsy Totsy club had a back room where Diamond often resolved business disputes, usually by shooting his opponents to death and then taking them out as if drunk.
The decline of the diamond began when on July 13, 1929, three unfair dockers got loaded and began a ruckus at the Hotsy Totsy Club Bar. Diamond jumped in with his gang member Charles Entratta to stop his manager. "I'm Jack Diamond and I run this place," Diamond told dockers. "If you don't calm down, I'll blow your (exemplary) head off."
The talking didn't work and the shooting started soon. When the smoke was cleared, two dock workers were dead and one was injured. As a result, Diamond and Entratta picked up this lamp. While hiding them, Diamond decided that the bartender and three witnesses had to be killed before he could go back for what he was doing. And soon they were. Cohen also died, and a hat check, cashier and a waiter disappeared from the ground. Diamond and Entratta calmly turned to the police and said, "I heard we were wanted for questioning." No charges were ever filed against them, but Diamond realized that New York City was no longer safe for him, which led him to close the Hotsy Totsy Club and move to New York State's Greene County in New York.
From New York State, Diamond led a small bootlegging operation. But after months of impatience, he sent the word back to the New York gangsters, namely Dutchman Schultz and Owney Madden, who, in his absence, had searched for the Diamond Rackets to return to take back what was his. This placed the target directly on Diamond's back and became known as the "underworld clay pigeon".
Diamond was sitting in a bar in Arato's inn near Arca, New York, when three men dressed as duck hunters broke into the bar and filled Diamond balls. The doctors gave him little chance of survival, but four weeks later, Diamond walked 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 left the roadside inn, four shots were fired; back, leg, lung and liver, but again he beat the odds given to him by the doctors and survived. He was not so lucky in December 1931 when, after a night of heavy drinking at the Kenmore Hotel in Albany, he drunk again in his nearby boarding house and fell asleep. After hearing three shots, he heard that he had heard Diamond praying for his life. Apparently, two gunsmiths had penetrated Diamond's room, and while one was holding him by the ears, the other had three slugs in his brain.
The killers fled Red Packard, ending the myth that Jack "Legs" Diamond was a gangster who couldn't be killed.