Irish bootlegger prospered and perished in Prohibition

Irishmen, native-born or sons of immigrants, played a significant role in the lawlessness. There were more than 60 known gangsters with Irish connections who helped the era gain its name - The Roaring Twenties.

Some, like Owney Madden whose parents came from County Longford, posed as legitimate businessmen (Madden ran the posh Manhattan night-spot, the Cotton Club).

Others were thugs, like the Donegal-born psychopath Vincent (Mad Dog) Coll. Both featured on recent Roamer pages. And then there was Jack Diamond, from County Sligo. He was as unscrupulous as the others but he achieved a reputation among the law-abiding population that gained him the name ‘Gentleman Jack.’

“This led to him being protected from the federal agents charged with enforcing Prohibition,’’ says Mitchell Smyth.

Ballycastle-born Smyth, a retired Canadian journalist and regular Roamer-contributor, learned the story of Gentleman Jack (and of Madden and Coll as well) when he was researching a feature on Prohibition for the Toronto Star.

Mitchell adds: “Unfortunately his popularity didn’t protect him from fellow gangsters, jealous of his success. He survived at least five assassination attempts, leading one enemy, New York crime boss Dutch Schultz, to lament: ‘How does he always bounce back?’”

Apart from the name Gentleman Jack, Diamond was known to the police and the newspapers as Legs Diamond. There are two theories on how he got the name Legs. One says it was because he was a great dancer; the other claims it came from the fact that he could (almost!) always outrun his assassins.

Jack Diamond was not even his real name. He was born on 10 July 1897 in Philadelphia, Pennsylvania, to John and Sara Moran, who had emigrated from Ireland six years earlier. The full name that they gave him was John Thomas Moran.

His mother died in 1913, and his father moved to Brooklyn, New York, where the teenager joined one of the vicious street gangs and adopted the name Jack Diamond.

He was 23 when Prohibition came and he was involved from the beginning, hijacking beer trucks and supplying booze to the ‘speakeasies’ (illicit taverns) that sprang up. But the young Irishman’s activities didn’t sit well with New York’s established crime boss, Dutch Schultz.

Time and again Diamond escaped death but he finally decided New York was too dangerous. That’s when he moved his ‘business’ to the Catskills Mountains, in central New York state. The Catskills is a resort area where New Yorkers flock to escape the summer heat and humidity of the city.

He soon became a Catskills celebrity. He attended dances in the posh resort hotels, where he and his wife Alice dazzled on the dance floor. People knew he was a bootlegger, but in the absence of legal liquor a bootlegger was everyone’s friend!

Legs had earlier bought a struggling brewery in Kingston, the gateway city to the Catskills, and it continued to operate, allegedly for export. Time and again Prohibition agents raided it but never found much beer.

It was only later that an elite band of agents, dubbed the Flying Squadron, found that a two-and-a-half inch pipe ran from the vats through the city’s sewers to a warehouse across town, where it was bottled and distributed.

Smyth says: “It tells a lot about Legs Diamond that the locals, especially the plumbers and the brewery workers, kept quiet about the secret pipeline.”

Business was booming when, in 1931, Legs was charged with kidnapping a rival gangster. On December 17 a court in Albany, the state capital, acquitted him.

He went celebrating that night with his mistress, showgirl Marion Roberts, then at 4:30am he returned, alone, to his hotel.

He was drunk and he let his guard down. He didn’t lock his room door before passing out on the bed.

Two hours later, two men entered the room.

One held him down while the other fired three bullets into the back of his head.

This time Dutch Schultz made sure that Legs Diamond didn’t ‘bounce back’.