Gangster Legs Diamond Escaped Death So Often, He Was Believed To Be Unkillable

Jack "Legs" Diamond stumbled into his rented apartment in Albany, New York. It was just before 5 a.m. on December 18, 1931, The Herald Statesman reported. The gangster and bootlegger had been celebrating his acquittal the day before on kidnapping charges in county court in Troy, just north of the city. The night started out at an Albany speakeasy on Broadway, where he drank with his wife and friends before he headed to his mistress' apartment and then back to his place to sleep (via "Hudson Valley Murder & Mayham"). He was still recovering from bullet wounds he'd suffered in an ambush near Cairo, New York, that April.

His young nephew, the only son of his dead brother, was asleep in another room, per the Evening Dispatch. As Legs fell into a deep sleep, he didn't hear the footsteps of the men who slowly made their way up the stairs toward his apartment on the second floor. Six shots suddenly lit up the dark room. According to the Abilene Daily Reporter, this was the fifth attempt on Legs' life since 1924. He'd cheated death so many times he earned a reputation for being unkillable. There was a joke among New York City's underworld denizens that Legs had so much lead in him from the many attempts on his life that he couldn't float in salt water, per the Daily News.

Early life and the first attempt

Born in Philadelphia, Jack T. Diamond and his younger brother, Edward Diamond, spent their youth running wild in the streets as members of the Boiler Gang following the early death of their mother. Jack's official birthdate is July 11, 1898, but his headstone has it as July 10, 1897. In an attempt to straighten out his children, their father moved the family to Brooklyn. Things only got worse there. Jack, who earned his nickname Legs for his love of dancing and his canny ability for outrunning the police, eventually acted as muscle for such notorious underworld figures as the gangster Jacob "Little Augie" Orgen and the gambler Arnold Rothstein.

Legs began hijacking the trucks of "Big Bill" Dwyer that were filled with bootleg liquor, which led to his first brush with death. In October 1924, a car filled with Dwyer's men pulled up next to Jack on Fifth Avenue in Manhattan and blasted away at him with shotguns and pistols (via New York Magazine). He made it out and drove himself to a nearby hospital, where doctors treated him for a scalp laceration and a bullet wound to the heel.

A rising star

Legs Diamond may have gotten away with only minor injuries the first time his rivals tried to murder him, but with the successive attempts, his wounds were more and more serious, helping to enhance the gangster's reputation for being impossible to rub out. Three years later, on October 15, 1927, Louis "Lepke" Buchalter and Jacob "Gurrah" Shapiro, former members of Little Augie's gang, turned on him and Diamond.

The two gangsters, who would go on to found Murder Inc., a group of underworld killers for hire, attempted to take over the gang by murdering Little Augie and Diamond, who was acting as the gang leader's bodyguard. While Little Augie and Legs strolled through Manhattan's Lower East Side that night, three men opened fire on them with automatics on the corner of Norfolk and Delancey Streets. Little Augie was shot in the head and died instantly, and Legs was shot in the back twice with one bullet piercing his lung (per the Daily News) and both ending up just below his heart (via the Arizona Daily Star). While some newspapers reported he was dying, Legs eventually made a full recovery and returned to his life as a gangster.

The Hotel Monticello

Legs Diamond continued to dodge death in Manhattan. On the morning of October 12, 1930 (as you can see October was not a good month for Legs), while at Manhattan's Hotel Monticello with his showgirl mistress, Marion "Kiki" Roberts, he was once again gunned down and left for dead. Two men shot him five times in his hotel room adjoining Kiki's. He stumbled out and collapsed in the hallway near the elevator. As he lay in his hospital bed with wounds in his lung and abdomen, among other areas, a Catholic priest gave him his Last Rites, The Brooklyn Daily Eagle reported.

No one expected him to live. He did, chalking his survival up to "two shots of whiskey," according to The New York Times. Diamond claimed he had no idea who would want to hurt him. He'd gained a bad reputation in the underworld for his ruthless attempts at horning in on other gangsters' territories. In this case, he was in the midst of trying to take over a Brooklyn beer racket. He finally wised up and headed upstate, where he had a summer home in Acra and the competition wasn't as fierce.

The Aratoga Inn

Outside of the Aratoga Inn, a roadhouse near Cairo, in the foothills of New York's Catskill Mountains, Legs Diamond and his men were ambushed by unknown assailants, most likely rival gangsters from New York City. It was just after midnight on April 27, 1931, when pistol flashes and shotgun blasts lit up the night. Legs fell to the ground. His lung — the same one hit by a bullet in the Hotel Monticello shooting less than a year earlier — had been perforated by buckshot, his scalp torn open, and a bone in his left arm shattered, among other wounds (per the Daily News).

One of his men dragged him back into the bar. "Help. I'm dying. I'm ... on the spot," Legs moaned, per "Hudson Valley Murder & Mayhem." At the hospital in Albany, he again began to slowly recover, a feat even more miraculous since he'd already been suffering from tuberculosis and stomach ulcers, not to mention his four previous brushes with death (per The Kansas City Star). "The bullet hasn't been made that can kill me," Legs boasted, per "Boss of Murder, Inc.:The Criminal Life of Albert Anastasia."

The end

Legs Diamond couldn't outrun his end, which came less than eight months later. While he slept, two men crept into his room and blasted away at him as he lay in bed. They were so close their pistols left scorch marks on his skin. Three .38 caliber slugs slammed into Diamond's head. One of the killers worried that Legs might not actually be dead — after all, he'd managed to survive four previous attempts to kill him. "Oh hell! That's enough! Come on!" the other man growled as they ran down the stairs and into a waiting car, according to The New York Times

The list of potential gangsters behind Legs' murder was long, yet his killing was never solved. By the time of his death, Diamond was pretty much broke. The only notable underworld figure left in Manhattan who didn't have a grudge against Legs, Owney Madden, paid for Diamond's funeral, which was held in Queens in a driving rain.