My local library rocks, when it’s not full of backpackers sating their wifi needs. Not only did I pick up Cold Print and Inglourious Basterds, but also Larry Writer’s excellent Razor, a history of East Sydney’s razor gangs of the 1920s to 1940s. Not only is it a fascinating read, but it also poses a few awkward questions.

Australia never had Prohibition per se, but in 1916, around 5000 soldiers rioted, looted and drank outer-suburban Liverpool dry, before heading into the centre of Sydney to do the same. After three days of drunken mayhem, the state government instituted the Liquor Act, and a referendum later that year saddled New South Wales with what was known as the Six-o’clock Swill: until it was repealed in 1955, pubs were banned from serving alcohol after 6pm.

In the wake of this, the “sly grog” trade sprang up, serving often watered-down drinks after hours; Sydney’s sly-groggeries were somewhat analogous to America’s speakeasies. By the Depression, many Sydneysiders couldn’t afford to go the track, but would bet nonetheless, so the provision of sly grog went arm-in-arm with prostitution, illegal, off-track SP betting and cocaine traffic.

Family legend has it that my grandfather was distantly descended from English and Spanish gentry, and (aside from one black sheep) my grandmother from decent, but hard-working, Scots and Irish migrants. But genealogy shows that both came largely from convict stock, transported to Australia in the late 18th and early 19th centuries.

In the late 1920s to the early 1940s—records show, for much longer than I’d been led to believe—my grandfather was a talented boxer. He and my grandmother drove taxis in central Sydney. At other times, he worked as a bookmaker; family whispers suggest that my grandfather’s bookmaking may have taken place off-track. (A rumoured feud with the Waterhouse family, however, hints that he may occasionally have seen horse flesh.)

My grandfather was in the habit of concealing cash about his person—the bag with his bookmaking takings was mostly rolls of banknote-sized pieces of newspaper, rolled up with only a few small-denomination notes on top. Presumably, this was to foil standover men, protection racketeers who specialise in victimising small-time criminals. (Mark “Chopper” Read is a relatively modern example.)

My grandmother always kept a loaded rifle in the house. And she was tough, never having trouble from male taxi passengers in that relatively lawless era, and—family legends once again attest—holding her own a couple of decades later in an on-air run-in with Germaine Greer.

At one point, at least, they were wealthy enough to afford waterfront property at the western end of the harbour. But in the early 1940s, as war raged across the world, they settled down: my grandfather enlisted and became a mechanic at de Havilland‘s facility near Bankstown Airport, and my grandmother raised their daughters, renovated a series of houses and ran a fruit-and-vegetable shop. They moved out to Fairfield, then (as now) home to many of Sydney’s New Australians. Although they never discussed it, it seems that their fortunes had waned.