On October 24, 1924, Diamond was shot and wounded by shotgun pellets, reportedly after trying to hijack liquor trucks belonging to a rival crime syndicate. On October 16, 1927, Diamond tried to stop the murder of "Little Augie" Orgen. Diamond's brother Eddie was Orgen's bodyguard, but Diamond substituted for Eddie that day. As Orgen and Diamond were walking down a street on Manhattan's
Lower East Side, three young men approached them and started shooting. Orgen was fatally wounded, and Diamond was shot twice below the heart. Diamond was taken to
Bellevue Hospital, where he eventually recovered. Police interviewed Diamond in the hospital, but he refused to identify any suspects or help the investigation in any way. Police initially suspected that Diamond was an accomplice and charged him with homicide, but the charge was dropped. The assailants were supposedly hired by
Louis Buchalter and
Gurrah Shapiro, who were seeking to encroach on Orgen's garment-district
labor rackets. On October 12, 1930, Diamond was shot and wounded at the Hotel Monticello on Manhattan's
West Side. Two men forced their way into Diamond's room and shot him five times. Still in his pajamas, Diamond staggered into the hallway and collapsed. When asked later by the police commissioner how he managed to walk out of the room, Diamond said he drank two shots of
whiskey first. Diamond was rushed to the Polyclinic Hospital, where he eventually recovered. He was discharged from Polyclinic on December 30, 1930. On April 21, 1931, Diamond was arrested in Catskill on assault charges for the Parks beating in 1930. Two days later, he was released from the county jail on $25,000
bond. Five days later, Diamond was again shot and wounded at the Aratoga Inn, a
road house near Cairo. After eating in the dining room with three companions, Diamond was shot three times and collapsed by the front door. A local resident drove Diamond to a hospital in
Albany, where he was reputed to have told the attending surgeon, "they have not yet made the bullet that will kill me." Diamond eventually recovered. On May 1, while Diamond was still in the hospital, the
New York State Police seized over $5,000 worth of illegal beer and alcohol from his hiding places in Cairo and at the Aratoga Inn. In August 1931, Diamond and Paul Quattrocchi went on trial for
bootlegging. ==Death==