Thursday, July 9, 2009

July 10: Jack "Legs" Diamond

Do you know who this is?
-He would survive four attempts on his life.
-He was pardoned for desertion from the Army by President Harding.
-He was nicknamed ‘Legs’ and ‘Gentleman Jim’.

He was a criminal – a kidnapper, bootlegger, numbers man, and much more – but he caught the public eye and fancy during the decade known as the Roaring Twenties. He would survive four attempts on his life in six years, and finally succumb to an attack in a rooming house in Albany, New York. While a popular figure to the public because of his flashy style and charismatic manner, he was an anathema his underworld brethren because of his self-centered acts – that included double-crossing and robbing them!

He was born on July 10, 1897 to John and Sara Diamond, Irish immigrants who settled in Philadelphia after their arrival in the United States in 1891. They would have their two children – Jack and Eddie - in Philadelphia. Both of the boys would struggle in school, and after their mother died in 1913 the father packed up the family and moved to Brooklyn, New York.

Lack of supervision allowed the boys to run wild, with their eventually joining a local gang called the “Hudson Dusters”. While his brother was more physically capable of surviving fights and feuds, Diamond’s specialty was creativity.

Jack “Legs” Diamond was seventeen when he had his first arrest was for the burglary of a jewelry store he broke into on February 4, 1914. Diamond would be in and out of jails for arrests until his death in 1931. He even served in the US Army during World War I, but would be convicted and jailed for desertion and theft from Fort Dix, New Jersey. After the war was over President Warren G. Harding released him under a blanket parole that was issued for more than two dozen Federal prisoners.

No one knew where “Legs” received his nickname. Perhaps it was because of his long legs – and his ability to use them to run from pursuing police officers. Or it may have been because of his ability on the dance floor of the nightclubs he loved to frequent. Or it might have been the nickname given to him by one of his gangland bosses. But, Legs was one of several nicknames Diamond had, including “Gentleman Jim”.

New York beckoned after Diamond was released from the ‘pen’, and soon Diamond found himself again involved in the ‘easy money’ criminal world that flourished during Prohibition. He worked with Lucky Luciano before Luciano hit the big-time, and in 1922 went to work for Arnold “The Brain” Rothstein. Diamond also worked for “Little Augie” Jacob Orgen, a New York gangster involved in bootlegging and labor racketeering. He began to form his own gang and began hijacking the trucks of other mobsters that were transporting illegal alcohol – a side-line that caused the first ‘hit’ to be ordered against him, almost ending his life.

Orgen had to fight to keep and expand his territory – and wealth and prestige. Diamond was hired as a bodyguard by Orgen, and then later spearheaded bootlegging activities that supplied many of the speakeasies in New York with illegal alcohol. However, there was a gangland struggle over the labor racketeering, and in 1927 Diamond was hospitalized during a drive-by shooting while walking with the target of the assassination – Little Augie. Little Augie died, Diamond was shot twice.

After recovering, Diamond went to work for Louis Buchalter – the man who had ordered the assassination of Little Augie. Diamond supervised bootlegging supplies to Manhattan speakeasies and night clubs. This job brought him into a running battle with his nemesis, Dutch Schultz. Schultz wanted to expand his criminal base of operations - and Diamond was one of those in his way. Diamond was shot on two separate occasions by Schultz’s men – once at a private dinner, where he was hit five times, and another when machine gun fire erupted at the Aratoga Inn, killing two bystanders and wounding Diamond three times. Through this series of attempts on his life, Diamond became known as the ‘clay pigeon of the underworld’.

Schultz actually wondered aloud at one point if there wasn’t anyone who could kill Diamond.

There was – and it occurred in the pre-dawn hours of December 18, 1931, in a room in Albany, New York, rooming house. Diamond had toured Europe after being shot in 1929, and while there his gang was forced out of New York by other gangs. When he returned, he decided to set up headquarters in Albany – a decision that was not appreciated by the city officials or police.

Diamond’s death hit the news racks through newsboy’s hawking “Extra, Extra” on the street corners.

Under a Albany Times Union newspaper banner headline that read "JACK DIAMOND SLAIN IN DOVE ST. HOUSE; KILLERS' WEAPON FOUND", a byline credited to H.L. Wood stated:

"Jack 'Legs' Diamond, survivor of a dozen skirmishes with the law and the lawless alike, today went from a clandestine tryst with Marion 'Kiki' Roberts, his showgirl sweetheart, to a tryst with death in an Albany rooming house.

"Unknown assassins, stalking down their prey with cool deliberation, pumped a stream of leaden pellets into the racketeer's head as he lay asleep in a small room at 67 Dove St.

"Death was instantaneous as the bullets furrowed the brain that had been set at rest a few hours earlier when a Rensselaer county Supreme court jury acquitted Diamond of a charge of kidnapping James Duncan, a Cairo youth."
The killers shot Diamond three times in the head while he was asleep. The killers were never identified, and could have been from rival gangs or the Albany police. He was buried in Mount Olivet Cemetery, Queens, New York.


There are no biographies available on 'Legs' Diamond at our local library


Find A Grave
Gangster City Profiles
Kiki’s Love
La Cosa Nostra
Mobster’s Murder
Murder Inc. blog
Paddy Whacked


D 01. Full Length Photo from 1931, Find-A-Grave by Ron Moody.
D 02. Mug Shot from the NYPD, Wikipedia
D 03. During Court appearance, Musicals


  1. Sounds like a fun guy to go party with. Other than the whole "Everyone Wants to Kill Him" part.

  2. Great post, last week the local oldies tv here had a 12 hour marathon of "The Untouchables"
    No Legs Diamond in that show as I remember but they might have, they did play with the truth just a bit.

  3. Check out Legs, by Albany writer William Kennedy (he also wrote Ironweed, and the screenplay for The Cotton Club). Fictionalized, but a great read by someone who really knows the area and the flavor of the times.

  4. Legs was an interesting character - handsome, ruthless, doublecrossing - but he had goals and ambition. He would have made a great businessman if he worked an area other than Prohibition.... He was like the energizer bunny - just kept going and going. Then his battery died.
    There was an Untouchable's episode on Legs - Season 2, episode 2. Steven Hill played 'Legs'.
    The book by Kennedy sounds good - I'll put it on my 'order from the Library list' and hope they can provide a copy from one of our Florida libraries.

  5. Hello all I am Timothy Diamond great cousin of jack legs grandmother is immediate cousin marguerite Ann Diamond.jack was handsome and aside his ruthlessness,he was a great family great aunt bernise diamond told me of sometimes he would comee bring ice cream for the kids.I agree if he had lived beyond prohibition he would've been very successful.