Mobster in America – Jack "Legacy" Diamond – The gangster who couldn’t be killed
Jack “Legs” Diamond was shot and badly wounded so many times that he was dubbed “The Gangster Who Couldn’t Be Killed.”
Diamond, born July 10, 1897, to parents from Kilrush, County Clare in Ireland, spent the early 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 assorted 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 in 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 Manhattan’s Lower East Side, where they hooked up with an up-and-coming gangster named Lucky Luciano. Diamond did several odd jobs for Luciano, including a little bootlegging, 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 Rothstein’s bodyguard, Rothstein brought Diamond in as a partner in his lucrative heroin business. When his pockets were sufficiently filled with cash and the need for Rothstein abated, Diamond, along with his brother Eddie he, 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, since 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 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 limo, but Diamond was too quick to be killed. He crouched down and stepped on the accelerator, not looking where he was going. Fortunately, he was able to escape the gunmen and drive himself to the nearby Mount Sinai Hospital. Doctors removed pellets from his head, face, and feet, and when the police arrived to question him, Diamond played dumb.
“I don’t know anything about it,” Diamond said to the fuzz. “Why would someone want to shoot me? They must have the wrong person.”
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 narcotics and bootlegging 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 standing guard for Orgen’s safety. Diamond was shot in the arms and legs (probably by accident), requiring another trip to the hospital. Upon his release, he made peace with Lepke and Shapiro, and as a result, the two assassins gave up Diamond Orgen’s narcotics and smuggling deals as a reward for being stupid enough to get in the way of the intended bullets. to Origin.
Now Diamond was on top of the world. He had plenty of money to spend, and he became a mainstay in all the best New York City nightclubs, 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, El Fay and the Stork Club, and his image frequently appeared in the newspapers, which portrayed Diamond not as a gangster, but as a dashing 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 his senior partner. The Hotsy Totsy Club had a back room where Diamond would frequently settle business disputes, usually shooting his adversaries to death and then carrying them out as if drunk.
Diamond’s downfall began when on July 13, 1929, three rebellious dockworkers charged up and started a riot at the bar of the Hotsy Totsy Club. Diamond jumped, with his gang member Charles Entratta, to save 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 (expletive) head off.”
Talking did not work and soon the shooting began. When the smoke cleared, two dock workers were dead and one wounded. As a result, Diamond and Entratta went on the run. While they were in hiding, Diamond decided that before he could go back to doing what he was doing, the bartender and three witnesses had to be killed. And soon they were. Cohen also turned up 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 could harm them, calmly turned themselves in to the police, saying, “I heard they were looking for us for questioning.” No charges were ever 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 a message to the New York City gangsters, namely Dutch Schultz and Owney Madden, who had picked up Diamond’s scams 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 showered 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 did it again. Nobody can kill Jack Legs Diamond.”
A few months later, as Diamond was leaving a roadside inn upstate, 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 drunkenly staggered back to his nearby boarding house room and fell asleep. The landlady later said she heard Diamond plead for his life, before hearing three shots. Apparently, two gunmen had 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.