Jack “Legs” Diamond, an Irish American gangster in Philadelphia and New York City during the Prohibition era also known as John Nolan and Gentleman Jack, is born in Philadelphia on July 10, 1897, to Sara and John Moran, who emigrated from Ireland to Philadelphia in 1891. A bootlegger and close associate of gambler Arnold Rothstein, he survives 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, his nemesis Dutch Schultz remarks to his own gang, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”

In 1899, Diamond’s younger brother Eddie is born. He and Eddie both struggle through grade school, and their mother suffers from severe arthritis and other health problems. She passes away on December 24, 1913, following complications brought on by a bacterial infection and a high fever. John Moran then moves his family to Brooklyn, New York.

Diamond soon joins a Manhattan street gang called the Hudson Dusters. His first arrest for burglary occurs when he breaks into a jewelry store on February 4, 1914. He serves in the United States Army in World War I but is convicted and jailed for desertion in 1918 or 1919. He serves two years of a three- to five-year sentence at Leavenworth Military Prison. After being released in 1921, he becomes a hired thug and later personal bodyguard for crime boss Arnold Rothstein.

Diamond is known for leading a rather flamboyant lifestyle. He is an 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 is never supportive of his life of crime but does not do much to dissuade him from it. He is a womanizer, with his best-known mistress being a showgirl and dancer, Marion “Kiki” Roberts.

In the late 1920s, Prohibition is in force, and the sale of beer and other alcoholic beverages is illegal in the United States. Diamond travels to Europe to acquire beer and narcotics but fails. However, he does obtain liquor, which is dumped overboard in partially full barrels that float to Long Island as ships enter New York Harbor. He pays children a nickel for every barrel they bring to his trucks.

Following the death of Jacob “Little Augie” Orgen, Diamond oversees illegal alcohol sales in downtown Manhattan via the Hotsy Totsy Club, an establishment partly owned by Diamond on Broadway. This work brings him into conflict with Dutch Schultz, who wants to move beyond his base in Harlem. He also runs into trouble with other gangs in the city. On July 14, 1929, he and fellow gang member Charles Entratta shoot three drunken brawlers in the Hotsy Totsy Club. Two of the brawlers, William Cassidy and Simon Walker, are killed, while the survivor, Peter Cassidy, is severely wounded. The club’s bartender, three waiters, and the hat check girl vanish, with one of them being found shot dead in New Jersey. He is not charged but is forced to close the club.

In 1930, Diamond and two henchmen kidnap truck driver Grover Parks in Cairo, New York, demanding to know where he had obtained his load of hard cider. When Parks denies carrying anything, Diamond and his men beat and tortured Parks, eventually letting him go. A few months later, he is charged with the kidnapping of James Duncan. He is sent to Catskill, New York, for his first trial, but is acquitted. However, he is convicted in a federal case on related charges and sentenced to four years in jail. He is tried in December 1931 in Troy, New York, also for kidnapping, and is once again acquitted.

On August 23, 1930, Diamond, under the false name John Nolan, boards the ocean liner SS Belgenland, bound for Europe. The New York City Police Department (NYPD) suspect that he might have left the U.S. aboard RMS Olympic or RMS Baltic, but he is not found on either ship when they reach Europe. The NYPD then sends a wireless telegraph message to the crew of SS Belgenland, who reply that a man similar to Diamond’s description is among the passengers. Diamond spends much of the voyage in the ship’s smoking-room playing poker, with one report claiming that he won thousands of dollars in this game. The SS Belgenland‘s officers, however, refute this, saying his winnings were small.

The NYPD telegraphs police in England, France and Belgium with the warning that Diamond is an undesirable character. When SS Belgenland reaches Plymouth on August 31, Scotland Yard officers tell Diamond he will not be allowed to land in England. He tells reporters that he wants to travel to the French spa town of Vichy for “the cure.” He disembarks in Antwerp on September 1, where Belgian police take him to their headquarters. Eventually, he agrees to voluntarily leave Belgium and is put on a train to Germany. When his train reaches Aachen, German police arrest him. On September 6, the German government decides to deport Diamond. He is driven to Hamburg and put on the cargo ship Hannover for passage to Philadelphia.

On September 23, Hannover arrives in Philadelphia, and Diamond is immediately arrested by the Philadelphia police. At a court hearing that day, the judge says he will release him if he leaves Philadelphia within the hour. Diamond agrees.

On October 24, 1924, Diamond is shot and wounded by shotgun pellets, reportedly after trying to hijack liquor trucks belonging to a rival crime syndicate.

On October 16, 1927, Diamond tries to stop the murder of “Little Augie” Orgen. His brother Eddie is Orgen’s bodyguard, but Diamond substitutes for Eddie that day. As Orgen and he are walking down a street on Manhattan’s Lower East Side, three young men approach them and start shooting. Orgen is fatally wounded, and Diamond is shot twice below the heart. He is taken to Bellevue Hospital, where he eventually recovers. Police interview him in the hospital, but he refuses to identify any suspects or help the investigation in any way. Police initially suspect that he is an accomplice and charge him with homicide, but the charge is dropped. The assailants are supposedly hired by Lepke Buchalter and Jacob “Gurrah” Shapiro, who are seeking to encroach on Orgen’s garment-district labor rackets.

On October 12, 1930, Diamond is shot and wounded at the Hotel Monticello on Manhattan’s West Side. Two men force their way into his room and shoot him five times. Still in his pajamas, he staggers into the hallway and collapses. When asked later by the police commissioner how he managed to walk out of the room, he says he drank two shots of whiskey first. He is rushed to the Polyclinic Hospital, where he eventually recovers. He is discharged from Polyclinic on December 30, 1930.

On April 21, 1931, Diamond is arrested in Catskill on assault charges for the Parks beating in 1930. Two days later, he is released from the county jail on $25,000 bond. Five days later, he is again shot and wounded at the Aratoga Inn, a roadhouse near Cairo. After eating in the dining room with three companions, he is shot three times and collapses by the front door. A local resident drives him to a hospital in Albany, where he eventually recovers. On May 1, while he is still in the hospital, the New York State Police seize over $5,000 worth of illegal beer and alcohol from his hiding places in Cairo and at the Aratoga Inn.

In August 1931, Diamond and Paul Quattrocchi go on trial for bootlegging. The same month, he is convicted and sentenced to four years in state prison. In September 1931, he appeals his conviction.

On December 18, 1931, Diamond’s enemies finally catch up with him. He is staying in a rooming house on Dove Street in Albany while on trial for kidnapping in Troy. On the night of his acquittal, December 17, he and his family and friends visit a restaurant in Albany. At 1:00 a.m., he and mistress, Marion “Kiki” Roberts, entertain themselves at the Rain-Bo Room of the Kenmore Hotel on North Pearl Street.

At 4:30 a.m., Diamond drunkenly goes back to the rooming house and passes out on his bed. Two gunmen enter his room about an hour later. One man holds Diamond down and the other shoots him three times in the back of the head.

There is much speculation as to who is responsible for the murder. Likely candidates include Schultz, the Oley Brothers, the Albany Police Department, and relatives of Red Cassidy, another Irish American gangster at the time. According to author William Kennedy in his book O Albany, Dan O’Connell, who runs the local Democratic political machine, orders Diamond’s execution, which is carried out by the Albany police.

Given the power that the O’Connell machine holds in Albany and its determination to prevent organized crime, other than their own, from threatening their monopoly of vice in the city, some accept this account of the story. For those believing this theory, William Fitzpatrick’s promotion to chief of police is said to be a reward for executing Diamond. In 1945, Chief Fitzpatrick is shot and killed in his own office by John McElveney, an Albany police detective. McElveney is sentenced to 20 years to life in prison. He is released in 1957 when his sentence is commuted by Governor W. Averell Harriman.

On December 23, 1931, Diamond is buried at Mount Olivet Cemetery in Maspeth, Queens. There is no church service or graveside ceremony. Family and spectators numbering 200 attend the interment. No criminal figures are spotted.

On July 1, 1933, Alice Kenny Diamond, Diamond’s 33-year-old widow, is found shot to death in her Brooklyn apartment. It is speculated that she is shot by Diamond’s enemies to keep her quiet.