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 a variety of robberies and mayhem, and after spending a few months in a juvenile hall, Diamond was drafted into the military. Military life did not suit Diamond very well. He served less than a year, then decided to go AWOL. He was soon captured and sentenced to three to five years at the Federal Penitentiary at Fort Leavenworth, Kansas.
Diamond was released from prison in 1921 and decided that New York City was where he could make his fortune. Diamond and his brother Eddie moved to the Lower East Side of Manhattan, where they hooked up with an up-and-coming gangster named Lucky Luciano. Diamond did various odd jobs for Luciano, including a small bootlegging job, 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 famous gambler and financial wizard. This was the break Diamond had been waiting for and he made the most of it.
After starting out as a bodyguard for Rothstein, Rothstein brought Diamond in as a partner in his lucrative heroin business. When his pockets became sufficiently filled with cash and Rothstein’s need diminished, Diamond, along with his brother Eddie, decided to expand on his account. They thought they could make a package by hijacking the smuggling trucks of other mobsters, including 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. In a very short time, Diamond became a persona non grata in the gangster world, and anyone who wanted to get rid of him could make a living.
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 rear window of the limousine, but Diamond was too quick to die. He crouched down and slammed on the gas, not looking where he was going. Fortunately, he was able to escape his shooters and drive himself to nearby Mount Sinai Hospital. Doctors removed buckshot from his head, face and feet, and when police arrived to question him, Diamond played dumb.
“I don’t know anything about it,” Diamond told the fuzz. “Why would anyone want to shoot me? They must have the wrong person.”
Soon, Diamond befriended a gangster who wasn’t looking to kill him. His name was “Little Augie” Orgen. Orgen installed Diamond as his main bodyguard. In exchange, 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 to death at the corner of Norfolk and Delancey Street, with Diamond supposedly keeping an eye on Orgen’s safety. Diamond was shot in the arms and legs (likely by accident), requiring another trip to the hospital. Upon his release, he made amends with Lepke and Shapiro, and as a result, the two assassins gave Diamond Origin’s smuggling and narcotics deals as a reward for being stupid enough to stand in the way of the intended bullets. to Orgen.
Now Diamond was on top of the world. He had plenty of money to spend, and became a mainstay in all of New York City’s best nightclubs, usually with showgirl Kiki Roberts on his arm, even though he was still married to his second wife, Alice Kenney. Diamond was seen regularly at the Cotton Club, El Fay, and the Stork Club, and his image frequently appeared in newspapers, which portrayed Diamond not as a gangster, but as a handsome man from the city. Soon Diamond was co-owner of the Hotsy Totsy Club on Broadway between 54th and 55th Streets, with Hymie Cohen as senior partner. The Hotsy Totsy Club had a back room where Diamond frequently settled business disputes, usually by shooting his opponents to death and then carrying them out as if they were drunk.
Diamond’s downfall began when on July 13, 1929, three unruly dockworkers charged and went on a rampage at the Hotsy Totsy Club bar. Diamond jumped, 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 dockworkers. “If you don’t calm down, I’ll blow your (expletive) head off.”
Talking didn’t work and soon the shooting started. When the smoke cleared, two port workers were dead and one was injured. As a result, Diamond and Entratta went on the run. While they were in hiding, Diamond decided that before he could do what he was doing again, the bartender 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 dropped off the face of the earth. Diamond and Entratta, along with anyone who might harm them, calmly surrendered to the police, saying, “I heard they were looking for us for questioning.” Charges were never filed 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 word to the New York City gangsters, namely Dutch Schultz and Owney Madden, who had picked up Diamond’s rackets in his absence, that he would return to take back what was his. This put a target right on Diamond’s back, and he became known as the “clay dove of the underworld”.
Diamond was sitting at the bar of the Aratoga Inn near Arca, New York, when three men dressed as duck hunters burst into the bar and filled Diamond with bullets. Doctors gave him little chance of survival, but four weeks later, Diamond was released from the hospital, telling the press, “Well, I’ve done it again. No one can kill Jack Legs Diamond.”
A few months later, as Diamond was leaving a roadside inn upstate, he was shot four times; in his back, leg, lung and liver, but again, he beat the odds the doctors gave him and survived. He wasn’t so lucky in December 1931, when after a night of heavy drinking at the Kenmore Hotel in Albany, he staggered drunkenly back to his nearby boarding house room and fell asleep. The landlady later said that she heard Diamond plead for his life, before hearing three shots. Two gunmen had apparently broken into Diamond’s room, and while one held him by both ears, the other put 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.