Time Out Sydney / Issue 13: February 6, 2008 - February 12, 2008

Sin City - Sydney's underbelly

A none-too nostalgic look into Sydney's heart of darkness

Sin City - Sydney's underbelly

1 Kings Cross

On Kellett Street on 9 August 1929, gangs loyal to Kate Leigh and Tilly Devine fought a pitched battle with guns and knives, leading to legislative crackdowns like the Consorting Act, which made it illegal for a felon to be in the company of other felons. Today it's a strip of cafes, including Piccolo's, fave haunt of Jeff Buckley and Billy Thorpe.

2 Darlinghurst

From 1822 to 1914, Darlinghurst Gaol held killers, rapists, bushrangers, poets (Henry Lawson and Bulletin founder JF Archibald were both incarcerated here) and all manner of miscreants. Public hangings (on Forbes Street) ceased in 1852, but hangman 'Nosy' Bob's gallows were only retired in 1907. These days it's home to the National Art School, the morgue is a fusebox station and tunnels still lead to the courthouse (the halls of justice, not the Taylor Square pub).

3 Surry Hills

Frog Hollow, now parkland on the corner of Riley and Albion Streets, was once the most vice-filled acre in the Commonwealth. Flimsy tenements piled on each other were home to gambling, drug dealing and prostitution. Samuel "Jewey" Freeman lived here in the 1920s, as did Kate Leigh before Sydney Council razed the site in 1925. The Hat Factory, the old CIB headquarters at 105 Campbell Street, was home to the Armed Hold- Up, Consorting and Special Breaking Squads among others. Metropolitan superintendent and former head of the CIB, Don Fergusson was found dead in a toilet adjacent to his offi ce in February, 1970. The coroner ruled suicide but early reports of two shots fired ten feet away indicated otherwise.

Kate Leigh's Devonshire Street terracewas home to 'Mum's' - one of her sly grog shops where citizens could pop in for a quiet drop when wowserism and early closing made life hell for the thirsty.

4 Chippendale

The Blackmarket Café (111 Regent Street) was synonymous with the sleaze of the Hellfire Club, but in 1997, three senior members of the Bandidos Motorcycle Club, including national president Michael Kulakowski and sergeant-at-arms Sasha Milenkovic were shot dead in the basement. The Bandidos tried to buy the building. It's now a café furniture showroom. The Anglican Press building in Queen Street was the scene of a great Sydney newspaper punch-up in June, 1960. Acting on orders from their father, a gang of men led by Kerry and Clyde Packer tried to occupy the Anglican Press plant. Operator Francis James called Rupert Murdoch who sent heavies to toss the Packers out on their ears. A knife's throw away is the Eveleigh Railyards in 1914, site of the first heist in Australia to use a getaway car. Thieves Samuel "Jewey" Freeman and Ernest "Shiner" Ryan were responsible. Six decades later, "Jockey" Smith was pinched casing the same payroll.

5 Woolloomooloo

Dr Nick Paltos's Palmer Street surgery boasted a who's who of crook crooks: Neddy Smith, Lennie McPherson, George Freeman and Danny Chubb. Paltos was jailed in 1986. A stroll up the hill was Tilly Devine's brothel at 191 Palmer Street, East Sydney, scene of wild parties, shootings, Devine's 1945 wedding and presumably quite a bit of horizontal refreshment. Up the hill is 234 Palmer Street's former bloodhouse du jour, the Tradesman's Arms hotel, now known as East Village. In the early 80s, two former prime ministers had offices in the Westfield building at 100 William Street. The Woodward Royal Commission into Drug Trafficking had a floor as did the Federal Police. All oblivious to the fact Danny Chubb used the Boulevard next door as a heroin clearing house.

6 West

Louisa Road, Birchgrove runs atop a finger of land the Wangal people used as a corridor to chase down kangaroos to spear at the end of the spit. In mid-1984 new tenants moved in and held weekend-long parties clogging the narrow street with cars. One Sunday, they set out for the carpark of the Viking Tavern at Milperra and mayhem ensued - six bikers and one bystander lay dead. Underworld king Lennie McPherson's home from the end of World War II until he was gaoled in the mid-1990s was 22 Prince Edward St, Gladesville. Sergeant Ray Briddick, a police prosecutor at Central, lived next door. Concord Repatriation Hospital is where Ronald Ryan booked his passage to the gallows. He was arrested on 6 January 1966 by Ray "Kicker" Kelly after a tip-off, probably from Lennie McPherson. Ryan and fellow Pentridge escapee Peter Walker thought they were meeting two nurses on a blind date - one was Kelly's favourite female cop, Del Fricker.

7 East

Tathmoor, a block of flats in Curlewis Street, Bondi, is where stick-up king "Jockey" Smith was gunned down in 1992, a day after being released from gaol. Jockey copped five slugs but survived to check out of hospital, go on the run, and later die in a police shoot-up. Sunbleached Brighton Boulevard today glows with bluechip property, but on 28 May, 1968, it was rocked by Sydney's first car bombing. Joe Borg, pimp, gunman and owner of most of the brothels in Darlinghurst, died when the ignition of his Holden ute set off 2kg of gelignite under the driver's seat. Animal lover Borg willed $250,000 to the RSPCA, it paid for the Yagoona shelter. Two child murders 26 years apart chilled Bondi to the marrow. Shortly after his father won the Opera House lottery in 1960, eight year old Graham Thorne was abducted outside his Edward street home, a crime that shocked the nation and one eerily echoed when Samantha Knight, 9, disappeared from her Bondi unit in 1986.

8 South

In January, 1965, the bodies of 15-yearold West Ryde girls Christine Sharrock and Marianne Schmidt were found in the Wanda dunes. Despite a huge reward, the murders are still unsolved. The Cronulla riots is one of the uglier events of Sydney's recent history. Word went around that 'Lebs' would be bashed at the popular Shire sand strip, bashings flared like brush fires and flags burned.

9 North

The Bogle-Chandler mystery hit the headlines on New Years Day 1963, after the bodies of Dr Bogle and Mrs Chandler were found in Lane Cove National Park. The deaths are now thought to have been caused by Lane Cove river emitting hydrogen sulfide gas at toxic levels. The Granny Killer's reign of terror lasted from March 1989 to 1990 leaving north shore's senior set apoplectic with terror. Pie salesman John Glover strangled six elderly women with their own pantyhose. He was arrested after attempting suicide in the home of his final victim.

Bookmark and ShareFeedbackNewsletterTwitter

Around Town

  • Email this to a friend
  • Print this page
  • Bookmark and Share
Your Name*

Your Email*

Recipient's Name*
Recipient's Email*
Message*