The Villain- Jack “Legs” Diamond

Updated: Aug 22

In IT GIVES YOU STRENGTH, the fictional characters interact with actual historic figures. Some of those historic characters are iconic for their courage, like Edith Cavell. The antagonist of the novel is gangster Jack “Legs” Diamond.


Although “Legs” Diamond always considered himself a giant of the Manhattan crime scene, Diamond, was a second rate thug compared to the leading mobsters of the day-Al Capone, Lucky Luciano, Bugsy Siegel, John Dillinger, Meyer Lansky, Arnold Rothstein, to name but a few. In fact, by the mid twenties, Diamond had either tried or successfully cheated every major crime figure in New York City, so the only way he could avoid gangland execution was by moving his operation to upstate New York. Indeed, Diamond was so hated among NYC mobsters, that they reportedly had given Dutch Schultz permission to kill Diamond on sight and takeover his NYC operation, even though Schultz was also universally distrusted and despised. Schultz tried and failed to kill Diamond multiple times before Diamond’s “move” to upstate New York. Although Diamond would tell people that this move upstate was by choice, Diamond’s banishment from NYC was driven by his desire to live.


Born in Philadelphia, the son of Irish immigrants, “Legs” Diamond was drafted into the United States Army in 1916 and, predictably, deserted before going off to war. Diamond was arrested, convicted of desertion and sentenced to three years in federal prison. In 1919, upon Diamond‘s release from prison, famed gambler Arnold Rothstein, who among other “accomplishments” is reputed to have fixed the 1919 World Series, hired Diamond as a bodyguard. However their relationship was short-lived. The old maxim “there is honor among thieves“ did not apply to Diamond. Not even thieves could trust “Legs”.


After double crossing virtually everyone with whom he did business by the mid-1920s, Diamond was given the moniker the “clay pigeon” as he narrowly survived several attempts on his life presumably made by Schultz. Thereafter, Diamond moved to upstate New York in 1926, where he married his sweetheart, Alice Schiffer, and they bought a home in Acra, New York.


Diamond became involved in the lucrative Upstate New York bootlegging business running alcohol from Canada to New York, which is how the business interests of Legs Diamond intersected with the business interests of fictional character and one of the protagonists of the novel Major Mike Kelly (ret.).


IT GIVES YOU STRENGTH launched the week of August 17, 2020.


© 2020, Philip Raymond Brown. Author of IT GIVES YOU STRENGTH