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Jack "Legs" Diamond

Jack "Legs" Diamond (born Jack Diamond; 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

Diamond was born July 10, 1897, to Sara and John Diamond, who emigrated from Ireland in 1891 to Philadelphia. 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 issues. 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 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.

On August 15, 1927, Diamond played a role in 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. 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. The assailants were supposedly hired by "Lepke" Louis Buchalter, who was 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. For a gangster, Diamond was also loyal, but was not averse to betraying someone when he saw fit. 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

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 score liquor which was dumped overboard in partially full barrels which floated into Long Island as ships entered New York. He paid the children a nickel for every drum 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 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 he was sentenced to four years in jail. In a third trial, in Troy, New York, he was acquitted.

Trip to Europe

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. 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. On September 6, the German government decided to deport Diamond. He was driven to Hamburg and placed on the freighter Hanover for passage to Philadelphia. On September 23, the Hanover 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.

Assassination attempts

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, shot him five times, and then fled. Still in his pajamas, Diamond staggered out 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. On December 30, 1930, Diamond was discharged from Polyclinic.

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 on $25,000 bond from the county jail.

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

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


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 am, Diamond went to visit his mistress, Marion "Kiki" Roberts. At 4:30 am, Diamond went back to the rooming house and passed out on his bed. Two gunmen entered his room around 5:30 AM. One man held down Diamond while the other shot him three times in the back of the head.

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 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. Chief Fitzpatrick himself was shot and killed in his own office by an Albany police detective, John McElveney, in 1945. Detective McElveney was sentenced to 20 years to life in prison. He was released in 1957, when his sentence was commuted by Governor 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.

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.