1925, "Legs" was driving on Fifth Avenue. A car pulled along side of him and explosion of gunfire erupted. Apparently sixty-four shotgun pellets peppered Jack’s body and head and .45 slug clipped his heal.
1927, Diamond and Jacob "Augie" Orgen were walking towards Rivington Street, when a dark sedan slowly pulled up behind them. Allegedly Louis Buchalter and a Jacob Shapiro got out of the car and walked directly behind Diamond and Orgen. Shapiro put a pistol to the back of Orgen’s head and put a bullet in his head. At the sound of the blast Diamond turned around as Buchalter shot him in the stomach.
1930, while Legs was staying the Monticello Hotel and he had a meeting with Salvatore Spitale and Irving Bitz. Later that night Spitale and Bitz returned. Gunshots echoed around the eighth floor, and two men were seen running from the hotel. Blood was pouring out of wounds from his right shoulder, left armpit, the centre of his chest, and his forehead. Jack owed Spitale and Bitz a large amount of money, and refused to pay it back.
1931, Diamond was at the Aratoga Inn in Cairo, upstate New York. He went to make a call and then stood out on the front porch. There was a blast from a shotgun, and then another as Jack fell to the floor. “Better luck next time” he reportedly said as the shooters fled in a car. Jack had one slug fracture his left arm, one in his right lung, liver, and one in his back. It’s believed he was shot for his attempt to take over the bootlegging in the Catskills, by ambushing deliveries and beating the drivers.
December 17, 1931, Jack had been acquitted on kidnapping charges in an Albany courtroom. That night he celebrated with family and friends at a restaurant. In the early hours of December 18, Jack went to see his mistress Kiki Roberts. At around 4.30am, he staggered back to his rooming house and passed out on his bed. It’s believed two men entered his room, one held Jack down, while the other shot him three times in the head, finally ending the life of Jack "Legs" Diamond
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https://www.youtube.com/watch?v=0KcuUqM1QD4