John "Legs" Diamond, alias Jack Moran (July 10, 1897-December 18, 1931), aka Gentleman Jack, was a famous Irish-American gangster in New York City during the Prohibition era. A bootlegger and close associate of gambler Arnold Rothstein, Diamond survived a number of attempts on his life between 1919 and 1931, causing him to be known as the "clay pigeon of the underworld." In 1930, Diamond's nemesis Dutch Schultz remarked to his own gang, "Ain't there nobody that can shoot this guy so he don't bounce back?" Jack Diamond was not related to Lucchese crime family associate, Stanley Diamond.
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Diamond was born July 10, 1897, to mother Sara and father John, who immigrated from Ireland in the fall of 1891 to 951 Frankford Ave, Philadelphia. In 1899, Jack's younger brother Eddie was born. Jack and Eddie both struggled through grade school, while Sara suffered from severe arthritis and other health issues. On December 24, 1913, Sara died from complications due to a bacterial infection and high fever. John Sr. moved to Brooklyn shortly afterwards. Diamond soon joined a New York street gang called the Hudson Dusters. Diamond's first arrest was for burglary; he broke into a jewelry store on February 4, 1914, with numerous arrests following through the remainder of his life. Diamond served in the U.S. Army during World War I, but deserted in 1918 or 1919, then was convicted and jailed for desertion.
After his release, Diamond was hired by "Little Augie" (Jacob Orgen) to murder an enemy, with Diamond then becoming Augie's personal bodyguard. Diamond was shot twice when Louis Buchalter, seeking to move in on Orgen's garment district labor rackets, shot and killed the latter.
Diamond was known for leading a rather flamboyant lifestyle. He was a very energetic individual; his nickname "Legs" derived either from his being a good dancer or from how fast he could escape his enemies. For a gangster, Diamond was also loyal, but was not averse to double-crossing someone when he saw fit. His wife, Alice Diamond was never supportive of his lifestyle, but didn't do much to dissuade him from it. Diamond was a womanizer; his best known mistress was showgirl and dancer Marion "Kiki" Roberts. The public loved Diamond; he was Upstate New York's biggest celebrity at the time.
During the late 1920s, Prohibition was taking place. The sale of beer and other alcohol was illegal in the United States. Diamond traveled to Europe to score beer and narcotics, but failed.
Following Orgen's death, Diamond went to work overseeing bootleg alcohol sales in downtown Manhattan. That brought him into conflict with Dutch Schultz, who wanted to move beyond his base in Harlem. He also ran into trouble with other gangs in the city. A young man named Stanley Wheeler befriended Diamond and served as his closest friend and driver on many of his quick getaways. Diamond failed to make a payment, and he was shot at the Hotel Monticello by gangsters. He then moved to the Catskills to get away from the threat of Schultz and others. Diamond was shot five times on one occasion when Schultz's men surprised him at a private dinner. With Wheeler driving him, he escaped with bullet holes in his car, and bullet wounds.
In 1930, Diamond and two henchmen kidnapped Grover Parks, a local truck driver, and demanded to know what kind of beer or alcohol he was carrying. After he denied that he was carrying anything, they beat and tortured him. They eventually let him go. A few months later, Diamond was charged with the kidnapping of James Duncan. He was sent to Catskill, New York for his first trial, but was acquitted. However, he was convicted on federal case on related charges, and he was sentenced to four years in jail. In a third trial, in Troy, New York, he was acquitted.
In early 1931, Schultz' gunmen fired on Diamond with machine guns at the Aratoga Inn near Cairo, New York, killing two bystanders in the process.
On December 18, 1931, Diamond's enemies finally caught up with him, shooting him after he had passed out at a hideout on Dove Street in Albany, New York after a night party on the day of his trial in Troy. The killers shot him three times in the back of the head at approximately 5:30 AM. However, six shots were heard, so there is reason to believe a minimal struggle took place. Had he not been killed, he would have gone on to serve the jail time mentioned above.
There has been much speculation as to who was responsible for the murder, including Dutch Schultz, the Oley Brothers (local thugs), the Albany Police Department, and relatives of Red Cassidy, another Irish gangster at the time. According to William Kennedy's 'O Albany, Democratic Party Chairman Dan O'Connell, who ran the local political machine, ordered Diamond's execution, which was carried out by the Albany Police. The following are Dan O'Connell's own words recorded during a 1974 interview by Kennedy and appears on pages 203 and 204:
O'Connell added that Fitzpatrick (a Police sergeant and future chief) and Diamond were "sitting in the same room and (Fitzpatrick) followed him out. Fitzpatrick told him he'd kill him if he didn't keep going."
Given the power that the O'Connell machine held in Albany and their determination to prevent organized crime other than their own from establishing itself in the city and threatening their monopoly of vice, most people accept this account of the story. In addition it has been confirmed by other former machine officials. Alice Diamond, his long suffering wife, was murdered two years after Legs. Chief Fitzpatrick himself was shot and killed in his own office by an Albany police detective in 1945. The detective who killed Chief Fitzpatrick served 20 years in prison.
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