Why you should care
Because he seemed bulletproof until he botched a big drug deal.
Jack “Legs” Diamond had just been acquitted of kidnapping charges at a trial in Troy, New York, and the dapper bootlegger was in the mood to celebrate. He and his entourage, including his wife, Alice, headed to a speakeasy in Albany, where Diamond cut out a little before one in the morning, saying he had to meet someone but he’d be back in a flash. Instead, he went to his mistress, Ziegfeld showgirl Marion “Kiki” Roberts, whom he was keeping in a nearby apartment during the trial. She was the last person to see him alive — except, of course, for his killers.
Diamond was no stranger to violence — he’d been shot four times — but his luck was running out. Known in the papers as the gangster who always got away, hence his nickname, Diamond was drunk when he returned to the rooming house in the early hours of Dec. 18, 1931, and soon passed out. Alice and the rest were pulling an all-nighter at the speakeasy. Two gunmen entered the premises at 5:30 a.m. One held Diamond down while the other blew the gangster’s brains out with a .38, pumping three bullets into the back of his head. Not even Legs Diamond could ankle away from that kind of hit.
Legs Diamond was the Al Capone of the East Coast, at least when it came to media coverage.
Scott Burnstein, author, Motor City Mafia
Born in Philadelphia in 1897 to recent Irish immigrants, Diamond moved to Brooklyn at age 15 with his father and younger brother, Eddie, after his mother died. He soon joined a gang called the Hudson Dusters and got started in crime. A year later, he was sent to jail for his part in a jewelry store smash-and-grab — the first of many encounters with the criminal justice system.
Jack and Eddie formed a gang that proved to be a force in the bootlegging racket, quickly gaining a reputation for strong-arm tactics. That was how gambler and bootlegger Arnold “Big Bankroll” Rothstein zeroed in on the brothers in 1919, not long after Jack got out of prison for desertion during World War I.
“A.R. needed security for his bootlegging investments,” says Christian Cipollini, author of Lucky Luciano: Mysterious Tales of a Gangland Legend. “Prohibition gangsters were constantly fighting over territory and stealing one another’s alcohol shipments. It was an incredibly lucrative and highly dangerous business to be in.”
The Diamond boys started working for Rothstein in various protection roles, be it bodyguard or hired gun, ensuring deals went down problem-free. Rothstein wasn’t a gangster himself; rather he was a forward-thinking businessman who understood and utilized the skills that only gangsters could provide. Unfortunately, Jack Diamond got a big head, and the publicity he courted — the bane of all serious mobsters — would eventually be his downfall.
“He was flamboyant and chronicled heavily in the New York press,” says Scott Burnstein, author of Motor City Mafia: A Century of Organized Crime in Detroit. “In a lot of ways, he was the Al Capone of the East Coast, at least when it came to media coverage.”
His relationship with Lucky Luciano, who for a time was part of the Diamond gang under Rothstein, deteriorated after frequent arrests, police questioning and a near-death ass kicking at the hands of Diamond-seeking cops. Luciano couldn’t be through with Diamond fast enough. Legs was a polarizing figure in the underworld and more than a few so-called friends turned enemies — especially after he botched the German connection.
Diamond decided to take a trip to Europe in the summer of 1930 with the intention of establishing a drug deal. Along for the ride were several cohorts, all former Rothstein minions, including Luciano. “The problem for Legs was that he took approximately $200,000 of investment money provided by Salvatore Spitale and Irving Bitz,” says Cipollini, referring to a pair of racketeers who would hit the papers in 1932 when Charles Lindbergh tried to hire them to negotiate the return of his kidnapped infant son. “And Legs didn’t return to America with money or a deal.” A big no-no in the world or organized crime. The list of people who wanted Diamond six feet under was growing by the day.
“They wanted him dead because he crossed them,” says Patrick Downey, author of Legs Diamond: Gangster. “Jack came back empty-handed and refused to return their money. It’s my opinion that Jack was bumped off by gunmen of Spitale and Bitz.”
With Diamond dead (Rothstein had been murdered a couple of years earlier), Luciano filled the vacuum and became capo di tutti capi, “boss of bosses,” in New York City. The transition ushered in the golden age of La Cosa Nostra and Luciano’s ascension to pop culture icon.
As for Legs Diamond, his notoriety faded and has largely been forgotten, unlike Capone and Diamond contemporaries like archrival Dutch Schultz. Historians and mob buffs, though, remember him as a pivotal mafioso who pioneered the nexus between traditional organized crime activities — gambling, loan-sharking, extortion and the like — and the emerging narcotics trade. But to pop culture, he’s an afterthought.