Also known as Gentleman Jack, Jack “Legs” Diamond was an Irish American gangster and bootlegger who became an international celebrity during Prohibition. In 1931 alone, he appeared in the New York Times 103 times, a fame that rivalled that of Al Capone.

He had made his money by running bootleg liquor from “Rum Row” – the name given to the coastal waters between New York and Atlantic City where much of the smuggled liquor was brought in – to the nightclubs and speakeasies of Manhattan, equipping his gang with sawn-off shotguns to discourage competitors and fend off hi-jackers. But one of the more spectacular episodes in Diamond’s career was when he was alleged to have walked into the Hotsy Totsy Club in New York and shot down the two owners in the midst of scores of dancing couples.

There isn’t a much less likely visitor to St James’s, but – reportedly – one day in the 1920s, Diamond and two of his gang swaggered into our shop at No.3. It is said that they made a substantial order, mostly for Scotch whisky (presumably because it would fetch the highest price back home), paid in cash and returned only to collect the goods the following day. Whoever dealt with them fortunately lived to tell the tale.

It was Diamond’s uncanny ability to survive attempts on his life that made his name – causing his arch-enemy Dutch Schultz to remark in 1930, “Ain’t there nobody that can shoot this guy so he don’t bounce back?” In 1931, someone finally did.

Legs Diamond is one of the customers that feature on our new tote bags, illustrated by John Broadley. Read more about him in this article from our archives.