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.
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.
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.
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
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.
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.