Legs Diamond

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Jack Diamond
Philadelphia mugshot of Jack Diamond, 1929
Born(1897-07-10)July 10, 1897
Philadelphia, Pennsylvania, US
DiedDecember 18, 1931(1931-12-18) (aged 34)
Cause of deathGunshot
Other namesGentleman Jack
Criminal chargeBurglary (February 14, 1914);
Desertion from US Army (1918–1919);
Kidnapping (1930)—sentenced to 4 years {twice acquitted}

Jack "Legs" Diamond (possibly born John Thomas Diamond, though disputed;[1][2] July 10, 1897 – December 18, 1931), also known as Gentleman Jack, was an Irish American gangster in Philadelphia and 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 1916 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?"

Early life[edit]

Diamond was born July 10, 1897, to Sara and John Diamond, who emigrated from Ireland in 1891 to Philadelphia, USA. In 1899, Jack's younger brother Eddie Diamond was born. Jack and Eddie both struggled through grade school, while Sara suffered from severe arthritis and other health problems. On December 24, 1913, Sara died from complications due to a bacterial infection and high fever. John Diamond, Sr. moved to Brooklyn shortly afterwards.

Diamond soon joined a New York street gang called the Hudson Dusters. Diamond's first arrest for burglary occurred when he broke into a jewelry store on February 4, 1914, with numerous arrests following throughout the rest 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.

Once free of jail, Diamond became a thug and later personal bodyguard for Arnold Rothstein in 1919.[3]

On October 16, 1927 Diamond tried to stop the murder of "Little Augie" (Jacob Orgen). Diamond's brother Eddie was Orgen's bodyguard, but Legs Diamond substituted for Eddie that day. As Orgen and Diamond were walking down a street on the Lower East Side of Manhattan, three young men approached them and started shooting. Orgen was fatally wounded and Diamond was shot two times below the heart. Diamond was taken to Bellevue Hospital, where he eventually recovered.[4] The police interviewed Diamond in the hospital, but he refused to identify any suspects or help the investigation in any way. The police initially suspected that Diamond was an accomplice and charged him with homicide, but the charge was later dropped.[5] The assailants were supposedly hired by Louis Buchalter and Gurrah Shapiro, who were seeking to move in on Orgen's garment district labor rackets.


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. His wife Alice was never supportive of his lifestyle, but did not 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 and the Manhattan Bootleg Wars[edit]

During the late 1920s, Prohibition was in force, and the sale of beer and other alcohol was illegal in the United States. Diamond traveled to Europe to score beer and narcotics, but failed. He did obtain liquor, which was dumped overboard in partially full barrels, which floated onto Long Island, as ships entered New York. He paid the children a nickel for every barrel they brought to his trucks.

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.

In 1930, Diamond and two henchmen kidnapped Grover Parks, a truck driver in Cairo, New York, and demanded to know where he had obtained his load of hard cider. When Parks denied carrying anything, Diamond and his men beat and tortured Parks, eventually letting 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 in a federal case on related charges, and sentenced to four years in jail. In a third trial, in Troy, New York, he was acquitted.

Trip to Europe[edit]

In late August, 1930, Diamond boarded the ocean liner Belgenland in New York for a voyage to Antwerp, Belgium. He told reporters that his final destination was Vichy in France, where he would take a "cure" of the mineral waters for his health. However, the real reason was to look for sources of rye whiskey in Germany to illegally import into the United States. During the trip, Diamond allegedly won several thousand dollars in poker games with other passengers, who treated him like a celebrity.[6] However, as soon as Diamond left the Belgenland, he was taken by Antwerp police to their headquarters. At the end of the day, Diamond agreed to voluntarily leave the country and was put on a train to Germany.

When Diamond's train reached the town of Aix-la-Chapelle (now Aachen) in Germany, agents of the German secret service arrested him.[7] On September 6, the German government decided to deport Diamond. He was driven to Hamburg and placed on the freighter Hannover for passage to Philadelphia.[8] On September 23, the Hannover arrived in Philadelphia and Diamond was immediately arrested by Philadelphia Police Department officers. At a court hearing that day, the judge said he would release Diamond if he left Philadelphia within the hour. Diamond agreed.[9]

Assassination and prosecution attempts[edit]

On October 12, 1930, Diamond was shot and wounded at the Hotel Monticello on the west side of Manhattan. Two men forced their way into Diamond's room and shot him five times before fleeing. Still in his pajamas, Diamond staggered into the hallway and collapsed. When asked later by the New York 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 in Manhattan, where he eventually recovered.[10] On December 30, 1930, Diamond was discharged from Polyclinic.[11]

On April 21, 1931, Diamond was arrested in Catskill, New York, on assault charges for the Parks beating in 1930. Two days later, he was released from the county jail on $25,000 bond.[12]

On April 27, 1931, Diamond was again shot and wounded, this time at the Aratoga Inn, a road house near Cairo, New York. After eating in the dining room with three companions, Diamond walked out to the front door. He was shot three times, and collapsed by the door. A local resident drove Diamond to a hospital in Albany, New York, where he eventually recovered.[13] On May 1, while Diamond was still in the hospital, New York State Troopers seized over $5,000 worth of illegal beer and alcohol from Diamond's hiding places in Cairo and at the Aratoga Inn.[14]

In August 1931, Diamond and Paul Quattrocchi went on trial for bootlegging.[11] That same month, Diamond was convicted and sentenced to four years in state prison. In September 1931, Diamond appealed his conviction.[15]


A narrow brick building with dark brown steps leading to the main entrance. Most of the upper two stories are obscured by a tree
House at 67 Dove Street, where Diamond was murdered in 1931

On December 18, 1931, Diamond's enemies finally caught up with him. Diamond had been staying in a rooming house in Albany, New York while on trial in Troy, New York, on kidnapping charges. On December 17, Diamond was acquitted. That night, Diamond, his family and friends were at a restaurant. At 1:00 a.m., Diamond went to visit his mistress, Marion "Kiki" Roberts. At 4:30 a.m., Diamond went back to the rooming house and passed out on his bed. Two gunmen entered his room around an hour later. One man held down Diamond while the other shot him three times in the back of the head.[16]

There has been much speculation as to who was responsible for the murder; likely candidates include Dutch Schultz, the Oley Brothers (local thugs), the Albany Police Department, and relatives of Red Cassidy, another Irish American 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 appear 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 brought him around once too often. Fitzpatrick finished Legs.

O'Connell added that William Fitzpatrick (a police sergeant at the time and later 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. Fitzpatrick's promotion to Chief of Police was believed to have been a reward for executing Diamond. In 1945, Chief Fitzpatrick himself was shot and killed in his own office by an Albany police detective, John McElveney. Detective McElveney was sentenced to 20 years to life in prison. He was released in 1957, when his sentence was commuted by Governor W. Averell Harriman.

On December 23, 1931, Jack Diamond was buried at Mt Olivet Cemetery in Maspeth, Queens. There was no church service or graveside ceremony. Two hundred family and spectators attended Diamond's interment; no criminal figures were spotted.[17]

On July 1, 1933, Diamond's widow, Alice Kenny Diamond, was found shot to death in her Brooklyn apartment. It was speculated that she was shot by Diamond's enemies to keep her quiet.[18]

See also[edit]

In popular culture[edit]


  1. ^ Elmaleh, Edmund (2009). The Canary Sang but Couldn't Fly. New York City: Union Square Press. p. 27. Retrieved October 21, 2015 – via Google Books.
  2. ^ https://www.amazon.com/Legs-Diamond-Gangster-Patrick-Downey/dp/1461088143#reader_1461088143
  3. ^ Newark, Tim (2010). Lucky Luciano, The Real and The Fake Gangster. New York: Thomas Dunne Books-St. Martin's Press. p. 31. ISBN 978-0-312-60182-9.
  4. ^ "'Little Augie' slain by rival gangsters" (PDF). The New York Times. October 16, 1927. Retrieved 5 May 2013.(subscription required)
  5. ^ "Diamond often accused" (PDF). The New York Times. October 13, 1930. Retrieved 29 April 2013.(subscription required)
  6. ^ "'Legs" Diamond is aboard liner Belgenland, wants to go to Vichy to "take cure"" (PDF). The New York Times. September 1, 1930. Retrieved 28 April 2013.(subscription required)
  7. ^ "German seize 'Legs" Diamond after expulsion from Belgium" (PDF). The New York Times. September 1, 1930. Retrieved 28 April 2013.(subscription required)
  8. ^ "Diamond on freighter on way to Quaker city" (PDF). The New York Times. September 6, 1930. Retrieved 28 April 2013.(subscription required)
  9. ^ "Diamond banished by Philadelphia" (PDF). The New York Times. September 23, 1930. Retrieved 28 April 2013.(subscription required)
  10. ^ "Jack Diamond shot five times by gunmen in a 64th street hotel" (PDF). The New York Times. October 13, 1930. Retrieved 28 April 2013.(subscription required)
  11. ^ a b "Diamond case goes to the jury today" (PDF). The New York Times. August 8, 1931. Retrieved 5 May 2013.(subscription required)
  12. ^ "Diamond gets bond; quits Catskill jail" (PDF). The New York Times. April 24, 1931. Retrieved 5 May 2013.(subscription required)
  13. ^ "'Legs" Diamond shot at inn in Catskills; condition critical" (PDF). The New York Times. April 27, 1931. Retrieved 28 April 2013.(subscription required)
  14. ^ "Diamond's cache of liquor is found" (PDF). The New York Times. May 2, 1941. Retrieved 5 May 2013.(subscription required)
  15. ^ "Jack Diamond Files Appeal" (PDF). The New York Times. September 12, 1931. Retrieved 5 May 2013.(subscription required)
  16. ^ "'Legs' Diamond Slain In Sleep At Albany By Two Assassins; Just Before Gang Murder". The New York Times. December 19, 1931. Retrieved August 9, 2012. Jack (Legs) Diamond, human ammunition dump for the underworld, was killed in a cheap rooming house at 67 Dove ...(subscription required)
  17. ^ "Gangdom is absent at Diamond burial" (PDF). The New York Times. December 23, 1931. Retrieved 5 May 2013.(subscription required)
  18. ^ "Diamond's widow murdered in home" (PDF). The New York Times. July 1, 1933. Retrieved 5 May 2013.(subscription required)
  19. ^ AFI's 10 Top 10 Ballot
  20. ^ Flops on CD – I to M
  21. ^ Ed McBain, "Running from Legs and Other Stories", Oxford : Compass Press, 2002.

Further reading[edit]

  • Adam, Fred. Fred Adam's St John's. St. John's, Nfld.: Creative Publishers, 1986. ISBN 978-0920021378
  • Curzon, Sam. Legs Diamond. Belmont Tower Books, 1973.
  • Downey, Patrick. Legs Diamond: Gangster. Createspace Independent Publishing Platform, 2011. ISBN 978-1461088141
  • Downey, Patrick. Gangster City: The History of the New York Underworld 1900–1935. Fort Lee, New Jersey: Barricade Books, 2004. ISBN 978-1569802670
  • Kennedy, William J. Legs. New York: Penguin Books, 1983. ISBN 978-0140064841
  • Levine, Gary. Anatomy of a Gangster: Jack "Legs" Diamond. South Brunswick & New York: A.S. Barnes & Company, 1979.
  • English, T.J. Paddy Whacked: The Untold Story of the Irish American Gangster. New York: William Morrow Paperbacks, 2006. ISBN 978-0060590031

External links[edit]