Kings Cross

David Whitley starts digging away at the often sordid secrets of Sydney’s ‘entertainment’ district, Kings Cross 
Under the largest advertising billboard in the southern hemisphere, it is lashing it down. But it’ll take a lot more than this deluge to wash the stains away. The Coca-Cola sign – so famous as a landmark and meeting place that it is now heritage listed – marks the gateway to Kings Cross, a place of notoriety, history and everything else in-between.

The squall of wind and rain seems fitting. To our right is Darlinghurst Road, long Sydney’s epicentre of fun and filth – the adjectives always depend on which side of the fence you sit on. It’s a place of 24 hour bars (some classy, some less so), strip clubs, shambling junkies and backpacker hostels. One person will be looking for somewhere to stay, another for somewhere that’ll still serve them when they can barely stand, another will be trying to entice all and sundry into a live sex show.

Yet, according to our guide, Kim, the Cross has dramatically cleaned up its act. “When I came here 30 years ago,” he says. “Everyone had a story about crook cops. I thought they were all too fantastical, then one by one they turned out to be true.”

He’s not claiming for a second that the Cross is squeaky clean – nightclub shootings, the legalised injecting room and the heroin-wrinkled dead stares of the prostitutes still out through desperation at 9am would make that a fanciful boast - “but you don’t hear those stories on the street anymore.”

The story of Kings Cross is one of debauchery. It can, says Kim, “be told through the criminals who ran it.”

And the first two major criminals were women. One, Tilly Devine, took advantage of a law that stated it was illegal for a man to make a living off the immoral earnings of women. There was nothing to say a woman couldn’t make a living off those immoral earnings, and she set up a series of brothels in the area. The taxman eventually caught up with her, and she had to sell the brothels off to a ruthless tough who had no family. When he died, most of his estate was left to the RSPCA. “They suddenly found themselves with 24 brothels – not exactly their core business,” says Kim.

On the other side was Kate Leigh, who took advantage of laws that shut pubs at 6pm, setting up “sly grog shops” across Kings Cross. The two had razor-wielding gangs that did their bidding throughout the 1920s and 30s. It culminated in a 40-man slashing brawl at the bottom of Kellett Street, now an odd little back lane where red-lit ‘Gentleman’s Clubs’ rub shoulders with restaurants and antique dealers.

Their era ended with master corruptor Abe Saffron in control throughout most of the 40s, 50s, 60s and 70s. Through blackmail and bribery, Saffron had an uncanny knack of getting those who had the power to shut him down in his pocket. Age and tax bills brought Saffron down, but the police ably filled the void of vice, drug-dealing and corruption themselves. The most alarming stories on the tour are of what the coppers got up to – such as the gauntlet of batons that drunken brawlers were forced to run at the back of the police station as they went inside from the van.

These days, Kings Cross is beginning to embrace its past. The pavements tell the stories of the blood spilt on them through a series of special golden paving slabs. Euphemisms about the ‘characters’ are out in force, but some tell the tales of the victims. Outside the Empire Hotel, a slab commemorates Juanita Nielsen – a local journalist who had the temerity to campaign against developments on Victoria Street. She went to a business meeting at what was then the Carousel Club, was herded up the stairs that can still be seen from the entrance today and was never seen again. All those who could possibly reveal the truth have since died. Darlinghurst Road wears many of its secrets on its sleeve; but it holds many more back forever.

Disclosure: David stayed at the Altamont in nearby Darlinghurst as a guest of Tourism Australia ( He did the Kings Cross tour with Two Feet and a Heartbeat (