35. “The Worst Woman in Sydney“
During the Jazz Era, Sydney’s major criminal kingpins were actually queenpins, running the city’s biggest gangs. One of them, Tilly Devine, the Queen of Woolloomooloo, was a former London prostitute who emigrated to Australia. There, she continued her career as a sex worker, and added to her repertoire a series of violent assaults – often with razors – that earned her a reputation as “The Worst Woman in Sydney“. She racked up 79 convictions in just five years, none of which carried serious penalties. That eventually changed, when she got two years in the State Reformatory for bloody assault.
While behind bars, Devine decided to change her life around. Not in the way the authorities wished, however: instead of a prostitute, she became a madam. The law at the time was phrased to state that men could not profit from the sale of sex. That left a loophole for female madams. Within a few years of her release, Devine was well on her to dominating Sydney’s sex trade. That brought her in conflict with Kate Leigh, another badass Sydney gang boss who resented Devine’s attempts to monopolize the city’s prostitution rackets.