Tough Nuts: Australia's Hardest Criminals

Tilly was a drug dealing brothel madam, a criminal sociopath and Sydney’s Queen of vice, who clawed her way to the top of the city’s sex trade with a razor in her hand. Tilly Devine was a prostitute who founded a criminal empire on the mean streets of Sydney after the First World War. She established a network of brothels, enslaved her working girls on cocaine and slashed, bashed and shot her way to the top of the criminal tree in Australia. Growing up as a child prostitute in London, Tilly met Jim Devine, an Australian soldier during World War One. Tilly arrived in Sydney as a war bride in 1920, only to find Jim putting her back on the game again. After five years working the streets, Tilly began building a network of brothels around the Palmer Street area of Woolloomooloo in inner city Sydney, with the violent drunken thug Jim as her partner. When the men reached for their cutthroat razors in gang fights, which proliferated in the 1920s, Tilly did the same, slashing the face of any man who got in her way. Her propensity for violence and the impulsive bursts of rage never left her and Tilly remained a sea of explosive anger to the day of her death in 1970. Tilly survived two World Wars and the Great Depression and became incredibly wealthy from the proceeds of her sex and drug empire. Like the gangster Al Capone, Tilly’s empire collapsed when she was pulled up by the Tax Office and handed a fine of 20,000 pounds. Tilly was forced to liquidate everything, and lost her empire overnight. By the time of her death in 1970, Tilly had become an embarrassment; an historical anomaly, a ghastly monster of a past that the people of Sydney no longer cared to dwell upon.