Although Jack “Legs” Diamond was a relatively low-level petty crook, he has become one of the most well-known 1920s Mafia figures in US history.
Legs Diamond was born in July 1897 to Irish immigrants in Philadelphia. Most sources have his real name as John Moran, though some have him born under the name John Nolan (an alias he would use later) and a few have it (probably inaccurately) as John Diamond. When his mother died in 1913 after a long illness, the family moved to New York City, where John and his brother Eddie became involved with the bands of Irish street toughs in the neighborhood. His first arrest came a year later when he was busted for burglarizing a jewelry store. He was sent to a juvenile reformatory, then was drafted into the US Army in 1917, as the US was entering the First World War. After a few months he went AWOL and deserted, but was caught and spent several years in Leavenworth.
When he was released in 1921, he made his way to Manhattan, where he and his brother Eddie did errands for Charles “Lucky” Luciano, who was then just a soldier in the New York Mafia. After a time, John, now calling himself “Jack Diamond”, became a bodyguard for Arnold “The Brain” Rothstein, the underworld’s financial wizard (perhaps most famous for fixing the 1919 World Series), and soon after he was running one of Rothstein’s heroin-smuggling rings.
But now the Diamond brothers made a bad decision. With Prohibition opening up a very profitable bootlegging industry, they decided to do a little side business of their own by selling illegal booze—but instead of brewing their own, they figured it would be easier to hijack beer and liquor trucks from other bootleggers. Since those operations were under the control of gangsters like Dutch Shultz, Meyer Lansky, and Rothstein himself, the Diamonds were stepping on some very powerful toes.
The response was quick and brutal. Luciano and Rothstein withdrew their protection, and in October 1924, Diamond was ambushed at a New York City street corner when another car pulled up next to his and poked a shotgun through the window, wounding him in the head and chest. Diamond managed to drive himself to the hospital.
After this, Diamond realized that he needed the shelter of an established gang, so he turned to the Jewish bootlegging operation run by Jacob “Little Augie” Orgen. Orgen, however, soon became the target of a takeover attempt by a larger operation run by Louis “Lepke” Buchalter and Jake “Gurrah” Shapiro. In October 1925, gunmen ambushed Orgen and Diamond as they walked down the street, killing Little Augie and wounding Diamond. The cops suspected that Diamond had set Augie up but couldn’t prove it, and Diamond was indeed placed in charge of some of Buchalter’s rackets.
Now awash with money, Diamond bought a speakeasy called the Hotsy Totsy Club on Broadway. That lasted until July 1929, when a brawl broke out in the bar and Diamond pulled a gun and shot two of the patrons dead and wounded another. The police never got to file any charges before all of the witnesses either had memory lapses or turned up dead.
But feeling the pressure, Diamond now left for Europe—where he was arrested by Belgian police, deported to Germany, was arrested there and deported to Philadelphia, were he was arrested yet again and released by a judge on condition that he leave the city. He went to New York—where in October 1930 he was shot and wounded by three gunmen.
The cops had a long list of suspects. By this time Diamond had earned the nickname “Legs”. Some sources attribute this to his presumed dancing ability, others say it was for his ability to scoot his way out of trouble and to escape death despite being shot so many times. It was also said, however, that “he never had a friend that he didn’t double-cross”, and there were plenty of gangsters in New York who wanted him dead. The press, meanwhile, fawned over him and treated him as a celebrity, calling him “Gentleman Jack”, and even though he was never a top-level mob boss like Capone, he was in the New York newspapers almost daily, with his flashy lifestyle (and his showgirl mistress) splashed both on the front page and in the society pages.
So Diamond fled the city and now tried to establish his own base of operations in Upstate New York. In 1931 he was arrested for assaulting and kidnapping a beer truck driver, and after posting bail he was shot and wounded yet again by unknown gunmen. (According to popular lore, it was at this time that his rival Dutch Schultz was heard to complain, “Ain’t there nobody who can shoot this guy so he don’t bounce back?”)
While still in the hospital, Diamond was arrested for bootlegging, but once again he beat the rap and was acquitted. But his luck had run out. A few days before Christmas 1931, Diamond returned to his home in Albany after a party to celebrate his acquittal. As he lay in bed two gunmen entered his room and shot him three times in the head. This time, he did not bounce back. Somebody had finally gotten to him. The murder remains unsolved.
Hidden History 