Legs Diamond, the Prohibition-era gangster known as Gentleman Jack, died on December 18, 1931, when gunmen entered his rented room in Albany, New York, and shot him three times in the back of the head. Diamond had passed out on his bed after a late night, and his body was found the next morning. His death ended a violent career marked by bootlegging, labor racketeering, and a string of assassination attempts that earned him the nickname “the clay pigeon of the underworld. ”
Born Jack Moran in Philadelphia, Diamond struggled through school while his mother, Sarah, suffered from severe arthritis and other health issues.
She died on December 24, 1913, from complications caused by a bacterial infection and high fever, and his father, John Moran, moved to Brooklyn shortly after. Diamond soon joined the Hudson Dusters, a New York street gang, and was first arrested for burglary on February 4, 1914, after breaking into a jewelry store. Diamond served in the United States Army during World War I but deserted in 1918 or 1919. He was convicted and imprisoned for his actions, serving two years of a three-to-five-year sentence at Leavenworth military prison.
After his release in 1921, he became a thug and eventually the personal bodyguard for Arnold Rothstein, a powerful crime leader. Diamond was known for his flamboyant lifestyle, with his nickname “Legs” coming either from his dancing ability or how quickly he fled his enemies. His wife, Alice, was never supportive of his lifestyle but did little to discourage him. Diamond was also a womanizer, with showgirl Marion “Kiki” Roberts being his most well-known mistress.
During Prohibition, Diamond and his younger brother Eddie began venturing into bootlegging, supplying Broadway nightclubs and speakeasies. Diamond also maintained his original primary occupation of labor slugging, and city officials in New York quickly began investigating union racketeering. Rothstein advised Diamond in 1927 through intermediaries, including Lewis “Lepke” Buchalter and, some sources claim, Meyer Lansky, to focus on infiltrating labor unions instead of traditional labor slugging and strong-arm tactics. On October 16, 1927, while walking on Norfolk Street in Manhattan’s Lower East Side, Diamond was shot and killed by gunmen.
The attack was one of several attempts on his life. Diamond was shot twice during the 1927 murder of Arnold Rothstein, standing in for his brother Eddie as Rothstein’s bodyguard. He was taken to Bellevue Hospital, where he eventually recovered. Police interviewed Diamond in the hospital, but he refused to identify any suspects or assist the investigation.
He was initially suspected of being an accomplice and was charged with homicide, but the charge was later dropped. The attackers were allegedly looking to break into Rothstein’s garment district labor rackets. Diamond was shot and wounded again on October 12, 1930, at the Hotel Monticello on Manhattan’s West Side. Two men broke into his room and shot him five times before fleeing.
Diamond collapsed in the hallway, still wearing his pajamas. When a New York police commissioner later asked how he got out of the room, Diamond reportedly said he drank two shots of whiskey first. He was rushed to Manhattan’s Polyclinic Hospital and eventually recovered. Diamond was shot again on April 27, 1931, at the Arisota Inn, a roadhouse near Cairo, New York.
He walked out the front door after eating in the dining room with three other people and was shot three times before collapsing. He was driven to a hospital in Albany, New York, by a local resident and eventually recovered. While he was still in the hospital, New York state troopers seized over five thousand dollars in illegal beer and alcohol from Diamond’s hideouts in Cairo and the Saratoga Inn. On May 1, 1931, Diamond and Paul Quattrosche were charged with bootlegging.
Diamond was convicted and sentenced to four years in state prison the same month, but he appealed the conviction in September 1931. Diamond had been staying in an Albany, New York, rooming house while on trial for kidnapping charges. He was acquitted on December 17. That night, he and his family and friends were at a restaurant, and he later went to see his mistress, Marion “Kiki” Roberts, at 1 a.
m. Diamond returned to the rooming house at 4:30 a. m. and passed out on his bed.
An hour later, two gunmen entered his room, restrained him, and shot him three times in the back of the head. The origin of the gunmen has been the subject of speculation. Dutch Schultz, local thugs, the Albany Police Department, and relatives of Red Cassidy, another Irish-American gangster, have all been mentioned as possible suspects. Some believed that Schultz ordered the killing to prevent Diamond from establishing himself in the city and threatening the Schultz organization’s monopoly on vice.
Others accepted the theory that Diamond was killed by police as a reward for Chief William Fitzpatrick’s promotion, or that relatives of Red Cassidy sought revenge. Gunmen entered Diamond’s room while he was asleep, and he was found dead the next morning. A small funeral was held, with about 200 family members and spectators in attendance, but no criminal figures were seen. Diamond’s widow, Alice Kinney Diamond, was found shot to death in her Brooklyn apartment on July 1, 1933, at the age of 33.
The murder of Legs Diamond marked the end of a violent era in New York’s underworld, leaving behind a legacy of crime, violence, and unanswered questions.