Mobster in America – Jack "Legs" Diamond – The Gangster Who Couldn’t Be Killed

Jack “Legs” Diamond was shot and injured badly so many times, he was called “The Gangster Who Couldn’t be Killed.”

Diamond, born on July 10th, 1897, of parents from Kilrush, County Clare in Ireland, spent the early years of his life in Philadelphia. After his mother died from a viral infection when Diamond was thirteen, he and his younger brother Eddie fell in with a group of toughs 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 reformatory, Diamond was drafted into the army. Army life did not suit Diamond too well. He served less than a year, then decided to go AWOL. He was soon caught 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 City was where he could make his fortune. Diamond and his brother Eddie relocated to Manhattan’s Lower East Side, where they fell in with an up-and-coming gangster named Lucky Luciano. Diamond did various odd jobs for Luciano, including a little bootlegging, in conjunction 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 notorious gambler and financial wizard. This was the break Diamond was waiting for and he made the best 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 full enough with cash, and his need for Rothstein diminished, Diamond, in concert with his brother Eddie, decided to branch out on their own. They figured they could make a bundle hijacking the bootlegging trucks of other mobsters, including those of Owney Madden and Big Bill Dwyer. This was not a very good idea, since Madden and Dwyer were part of a bigger syndicate of criminals, that included Luciano, Dutch Schultz and Meyer Lansky. In no time, Diamond was persona non grata in the gangster world, and free pickings for anyone who wanted to get rid of him.

In October of 1924, Diamond was driving a Dodge sedan up Fifth Avenue, when at 110 Street, a black limo pulled along side him. A shotgun fired at Diamond from the back window of the limo, but Diamond was too quick to be killed. He ducked down and hit the accelerator, without looking where he was going. Luckily, he was able to escape his shooters and drive himself to nearby Mount Sinai Hospital. The doctors removed pellets in his head, face and feet, and when the cops arrived to question him, Diamond dummied up.

“I dunno a thing about it,” Diamond told the fuzz. “Why would anyone want to shoot me? They must of got the wrong guy.”

Soon Diamond became friends with a gangster not looking to kill him. His name was “Little Augie” Orgen. Orgen installed Diamond as his chief bodyguard. In return, Orgen gave Diamond a nice share of his bootlegging and narcotics business. This friendship went just fine, until October 15, 1927, when Louis Lepke and Gurrah Shapiro gunned down Orgen on the corner of Norfolk and Delancey Street, with Diamond supposedly standing guard over Orgen’s safety. Diamond was shot in the arms and legs (probably by accident), necessitating another trip to the hospital. Upon his release, he made nice with Lepke and Shapiro, and as a result, the two killers gave Diamond Orgen’s bootlegging and narcotics businesses, as a reward for being stupid enough to get in the way of bullets meant for Orgen.

Now Diamond was on top of the world. He had plenty of cash to throw around, and he became a mainstay in all of New York City top nightclubs, usually with showgirl Kiki Roberts on his arm, despite the fact he was still married to his second wife Alice Kenny. Diamond was seen regularly at the Cotton Club, El Fay and the Stork Club, and his picture was frequently in the newspapers, which portrayed Diamond not as a gangster, but as a handsome man-about-town. Soon Diamond was part owner of the Hotsy Totsy Club on Broadway between 54th and 55th Street, with Hymie Cohen as his fronting partner. The Hotsy Totsy Club had a back room where Diamond frequently settled business disputes, usually by shooting his adversaries to death, then carrying them out as if they were drunk.

Diamond’s downfall started, when on July, 13, 1929, three unruly dockworkers got loaded and started a ruckus at the bar of the Hotsy Totsy Club. Diamond jumped in, with his gang member Charles Entratta, to stop his manager from being throttled. “I’m Jack Diamond and I run this place,” Diamond told the dockworkers. “If you don’t calm down, I’ll blow your (expletive) heads off.”

Talking didn’t work and soon the shooting started. When the smoke cleared, two dockworkers were dead and one injured. As a result, Diamond and Entratta took it on the lam. 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 turned up dead too, and the hat check girl, the cashier and one waiter disappeared from the face of the earth. Diamond and Entratta, with everyone out of the way who could possibly harm them, calmly turned themselves into the police and said, “I heard we were wanted for questioning.” No charges were ever brought against them, but Diamond realized New York City was no longer safe for him, so he closed the Hotsy Totsy Club and relocated to Greene County in upstate, New York.

From upstate New York, Diamond ran a little bootlegging operation. But after a few months of impatience, he sent word back to gangsters in New York City, namely Dutch Schultz and Owney Madden, who had scooped up Diamond’s rackets in his absence, that he was coming back to take back what was his. This put a target right on Diamond’s back, and he became known as the “clay pigeon of the underworld.”

Diamond was sitting at the bar of the Aratoga Inn near Arca, New York, when three men dressed as duck hunters barreled into the bar and filled Diamond with bullets. The doctors gave him little chance for survival, but four weeks later, Diamond walked out of the hospital and told the press, “Well, I made it again. Nobody can kill Jack Legs Diamond.”

A few months later, as Diamond was leaving an upstate roadside inn, was shot four times; in the back, leg, lung and liver, but again, he beat the odds the doctors gave him, and survived. He was not so lucky in December of 1931, when after a night of heavy drinking at the Kenmore Hotel in Albany, he staggered back drunk to his nearby boarding room and fell asleep. The landlady said afterwards that she heard Diamond pleading for his life, before she heard three shots. Apparently two gunman had burst into Diamond’s room, and while one held him by his two ears, the other put three slugs into his brain.

The killers escaped in a red Packard, putting an end to the myth that Jack “Legs” Diamond was the gangster who couldn’t be killed.