Sydney's 1920s–1940s Criminal Underworld: Rare Photos From Police Archives (10 photos)

A mother-daughter cocaine ring and a gang of thieves who dressed in drag to rob American servicemen are among the underworld figures captured in a rare collection of photos from 1920s–1940s Sydney, uncovered in police archives. Drawn from the NSW Police Forensic Archive, the black-and-white mugshots feature a colorful gallery of rogues—including Ada McGuinness, once dubbed "Sydney's evilest woman."







Ada and her daughter, Hazel McGuinness, were arrested and taken to Central Police Station in July 1929 for dealing and possessing cocaine out of their home in the Sydney suburb of Darlinghurst. Police considered Ada McGuinness to be one of the city's most prolific drug dealers.





In her station mugshot, Hazel appears remorseful, but Sydney living history museum curator Peter Doyle notes that the young woman never stood a chance: she was turned in by her own mother, who was deeply involved in prostitution, smuggling, and drug trafficking.



Another striking pair is 18-year-old Neville McQuade and 19-year-old Lewis Keith, pictured here dressed in women's clothing outside Sydney's North Police Station in June 1942. The pair were charged with offensive behavior, and officers found stolen US currency and military uniforms among their belongings.

At the time, scammers frequently targeted gay American servicemen stationed in Australia during World War II, according to Peter Doyle: "One would go out on a date while the other ransacked the apartment."

At the time of his arrest, McQuade told a local newspaper about his urge to impersonate women. The exhibition, titled City of Shadows, is on permanent display at the Justice & Police Museum, featuring not just traditional criminal mugshots, but portraits capturing the unique personal quirks of each suspect.



One of the exhibition's most captivating portraits is that of Herbert Ellis, a notorious safe-cracker.



Alfred Ladewig, nicknamed "Tiny," was a con artist and pickpocket who worked his way through Brisbane, Sydney, and Melbourne. He was arrested in Sydney in the early 1920s on charges originating in Brisbane, and this photo was taken before his extradition to Queensland. The image looks more like a studio portrait than a police mugshot.



De Gracie and Edward Dalton were arrested in the early 1920s on fraud charges.