As the site of some of Australia’s most notorious criminal gangland activity, Sydney’s past teems with tales of bawdy bordellos, sordid soirees and rapacious razor gangs.

It can be hard to think of Sydney as anything other than a bastion of delicate pleasures and devil-may-care whimsy. But for history lovers, Sydney offers so much more than a pleasant trip aboard a ferry and a few dizzingly expensive meals.

As the site of some of Australia’s most notorious criminal gangland activity, Sydney’s past teems with tales of bawdy bordellos, sordid soirees and rapacious razor gangs. As the world emerged from the shadow of the Great War, drugs, booze and prostitution became the criminal order of the day – and no more so than within the belly of Sydney’s bloodthirsty razor gangs.

From the ragged streets of Surrey Hills and Darlinghurst emerged two unlikely kingpins to rule over everyone – unlikely because these two kings were queens. Tilly Devine and Kate Leigh presided over their empires for years, establishing most of their power during the late 1920s. Taking advantage of a legal loophole that denied men the right to profit from women’s “immoral” behaviour but made no mention of women doing the same, Devine and Leigh became Sydney’s most notorious madams and drug dealers. With their own respective gangs looking after their interests, they fended off attempts from all sides – including each other – to maintain their place at the top of the heap.

It is easy to take your own walking tour to follow the trajectory of these key moments, though tours are also available with groups like Razorhurst. So, don your best cloche, wing tips and silk stockings and lift that invisible veil that separates the ages with these highlights.

Kate Leigh’s Sly Grog Shop
Leigh had already been operating a lucrative criminal business for years before the emergence of razor gang warfare. Capitalising on the enforcement of the so-called six o’clock Swill (instituted in 1916 following a riot of 5,000 ANZAC soldiers high on grog), Leigh was the queen of the sly grog shop. Described by papers as “the most evil woman in Sydney”, Leigh’s main dispensary was a flat above her fruit and vegetable shop at 212 Devonshire Street, Surrey Hills. It was also the site of her death in 1964, at age 82. She had been known as one of Sydney’s wealthiest, most charismatic women and more than 700 people attended her funeral – including police officers and politicians.

Frog Hollow
From Devonshire Street, turn left onto Riley Street and walk to the corner of Albion Street.
Most slums would be seen as middle class boroughs in comparison to Frog Hollow. Razed to the ground in the late 1920s, it was a hiding place for criminals, prostitutes and violent thugs. Its swamp-like ground housed frogs in the mid 1800s, but even they abandoned the vile, vermin-infested horrors that lay within. Home to Samuel “Jewey” Freeman, leader of the Riley Street Gang and former lover to Leigh, it was the site of unimaginable poverty and violence.

King’s Lane
Continue up Riley Street towards Darlinghurst. Cross over Oxford and Burton Streets.
King’s Lane was the stomping ground for Norman Bruhn’s gang, Sydney’s most violent criminal and master wielder of the razor. With Snowy Cutmore, George “the Midnight Raper” Wallace (whose moniker manages to be both frightening and brutally straightforward) and Razor Jack Hayes, Bruhn terrorised the local populace. Busting out of Melbourne before a court hearing, Bruhn was feared for his garrotting skills: with one hand he would tighten a leather thong around his victim’s neck, while calmly pick-pocketing him with the other. 

The Tradesman’s Arms
Head east on King’s Lane to Palmer Sreet to arrive at the site of the old Tradesman’s Arms

Directly across from Devine’s home at 191 Palmer Street, the Arms was a literal den of iniquity. With sawdust coating the floor to soak up blood and vomit, it was the site of illegal bootlegging, drug dealing and gambling. Devine operated one of the most lucrative brothel networks in Sydney and often called in to transact business at the Arms.

From Palmer Street, turn left onto Liverpool Street and head towards Whitlam Square. Turn right onto Charlotte Lane.
After breaking an unspoken agreement regarding territories and gang leaders, Bruhn was led to Charlotte Lane and shot by an unknown assassin at Mack’s, a sleazy cocaine and sly grog den. Bruhn had held up Mack’s shortly prior to his murder.

The Battle of Blood Alley
Walk north to William Street and turn right. Head east until you arrive at Kellet Street.
Site of one of the most bloodthirsty razor gang riots of the period, the Battle of Blood Alley saw Devine’s boys match up against Leigh’s in their endless pursuit of dominance. Kellet Street was a reviled strip of brothels and seedy houses and provided an appropriate backdrop for the 40 strong riot that saw razors, fisticuffs, boots and other weapons wielded against each other. More than a dozen people sustained serious injuries in the riot.

Double back to 99 William Street to finish the tour at the Strand Hotel, where Devine ‘s notorious henchman brazenly shot and killed two of Leigh’s men. Order yourself up a gin and tonic or a double nip of whiskey and ponder the seedy underside of Sydney’s criminal history, where there were seemingly no rules and the clothes were as sharp as the razors.

The article 'A walk through Sydney’s criminal shadows' was published in partnership with Lonely Planet.