Jack Diamond (gangster)

Jack "Legs" Diamond (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 soldier, Stanley Diamond.

Early life

Born July 10, 1897 to Mother Sara and Father John, who immigrated from Ireland in the fall of 1891 to 2350 E. Albert Street, Philadelphia, Pa. In 1899, Jack's younger brother Eddie was born. Jack and Eddie both struggled through grade school while Sara suffered with severe Arthritis and other health issues. On December 24,1913 Sara died from complications due to a bacterial infection and high fever. John Sr. gave notice to his factory job, packed up his belongings and his sons and moved to Brooklyn, NY. Diamond soon joined a New York street gang called the Hudson Dusters. Diamond's first arrest record was for Burglary; breaking into a jewelry store on 2/4/14. Many other arrests followed between 1914 and 1931. Diamond later served in the U.S. Army, but deserted; in 1918-1919, he was convicted and jailed for desertion.

After his release from prison, Diamond was hired by "Little Augie" Jacob Orgen to murder an enemy. Diamond became Augie's personal bodyguard. He was shot twice when Louis Buchalter, seeking to move in on the labor rackets that Orgen was running in the garment district, shot and killed Orgen.


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, Fact|date=September 2007 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.

Prohibition & the Manhattan Bootleg Wars

During the late 1920s, Prohibition was taking place. The sale of beer and other alcohol was illegal in the United States. This, however, did not stop Diamond, nor anyone else in the crime business, from closing shop. He travelled to Europe for a couple of months, hoping to score beer and narcotics that way, but he came back unsuccessful.

Following Orgen's death, Diamond went to work overseeing bootleg alcohol sales in downtown Manhattan. That brought him into conflict with Dutch Schultz, who planned to move beyond his base in Harlem. He also ran into trouble with other gangs in the city, and on one occasion, after failing to make a payment, he was shot at in the Hotel Monticello. He then moved up to the Catskills to get away from the threat of Schultz and the others. It wasn't enough. Diamond was shot five times on one occasion when Schultz's men surprised him at a private dinner. He managed to escape, getting bullets torn into the back of his car, as well as various locations on his body.

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, a federal case on related charges case turned out different, and he was sentenced to four years in jail. A third trial, in Troy, New York however, also saw an acquittal.

On another occasion in early 1931, Schultz' gunmen opened up 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, there were six shots heard, so there's 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), and the Albany Police Department. 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:

:"In order for the Mafia to move in they had to have protection, and they know they'll never get it in this town. We settled that years ago. Legs Diamond...called up one day and said he wanted to go into the 'insurance' business here. He was going to sell strong-arm 'protection' to the merchants. I sent word to him that he wasn't going to do any business in Albany and we didn't expect to see him in town the next morning. He never started anything here."

:"Prior brought him around here...but he brought him around once too often. Fitzpatrick finished Legs."

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.

In popular culture

* The first book in author William Kennedy's "Albany" series, "Legs", follows Diamond to his death.
* Diamond is the subject of director Budd Boetticher's 1960 film "The Rise and Fall of Legs Diamond" starring Ray Danton and Warren Oates. A 1988 musical based on the movie starred Peter Allen, but it lasted just 64 performances and is regarded as one of Broadway's legendary high-profile flops. [ [http://www.musicals101.com/flops3.htm Flops on CD - I to M ] ]
*Wu-Tang Clan-member Raekwon the Chef's debut hip hop album "Only Built for Cuban Linx" features a mafioso theme in which he and each guest artist assume a "Wu-Gambino" nickname. Raekwon's nickname is "Lex Diamond" in homage to Legs Diamond.
*A Terry Gilliam animation sequence from the British TV show "Monty Python's Flying Circus" features a gangster chicken by the name of "Eggs" Diamond.

Further reading

*Levine, Gary. "Anatomy of a Gangster: Jack "Legs" Diamond", Purple Mountain Press, 1979.
*Curzon, Sam. "Legs Diamond", Belmont Tower Books, 1973.
*Kennedy, William. "O Albany", Viking Penguin Inc, 1983.
*Downey, Patrick. "Gangster City: The History of the New York Underworld 1900-1935". Fort Lee, New Jersey: Barricade Books, 2004.
*Adam, Fred. "Fred Adam's St John's". There is a picture of Jack Legs Diamond with Jack Johnston taxi driver or owner of Blue Taxi in St. John's Newfoundland in 1920. Diamond is photographed wearing diamond patterned socks.


External links

* [http://www.patrickdowney.com/profile-legs.html Gangster City Profiles: Jack "Legs" Diamond]

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