Kate Leigh and Tilly Devine are remembered in Sydney’s Surry Hills, Darlinghurst and Woolloomooloo as the Queens of the Underworld.  Together through this period these two women controlled Sydney’s supply of sly-grog, narcotics and prostitutes, running gangs of stand over men, razor slashers and enforcers as well.  They also hated each other and were not afraid to fight, shoot or slash anyone who got in their way, each other included.

Kate came to Sydney as a young girl from Dubbo, sent to the Parramatta Industrial School for Girls as a neglected child.  She married a petty crim in 1902 and started down her colourful life path.  In 1914 she gave a false alibi for her then boyfriend Ernest Shiner Ryan, who had held up the payroll at Eveleigh Railyard using a getaway car for the first time in Australia.  Kate went to prison for perjury. 

When she was back on the streets, 6 o’çlock closing had created one of the all time great business opportunities, sly grog.  Between 1919 and 1954 Kate was the main sly grog provider to Sydney’s thirsty drinkers, running her booze empire out of her home in Surry Hills, she soon diversified into illegal gambling, prostitution and cocaine.  

Kate's 1930 Mug Shot
Kate's 1930 Mug Shot

Although known as the Queen of the Underworld she was rarely convicted and spent little time in jail.  Locals remembered her as someone to respect and fear, but also someone who was generous with her money and who through Christmas parties every year for the poor neighbourhood kids.  In 1954 the tax man caught her and he was declared bankrupt, the year before 6 o’clock closing finished and ruined her business.  She died a poor woman in 1964.

Kate’s main rival was Tilly Devine, whose territory covered Darlinghurst and Woolloomooloo.  Tilly was a war bride, having married Jim Devine, an Anzac and thug, in Britain when she was just 16 and followed him to Australia. 

She started work as a prostitute for her new husband immediately (taking up where she had left off in Britain) and started gaining her prodigious record: between 1921 and 1925 she was arrested 79 times!  As Jim became more involved in the underworld, so too did Tilly.  One curious legal loophole which helped Tilly (and Kate) was that women were not mentioned in any laws about brothel keeping, being it was illegal for men to run brothels, but technically not women.  Tilly exploited this fully and soon had over 18 houses where she ran her prostitutes from in East Sydney. 

Known variously as Queen of the Night, the Worst Woman in Sydney and eventually Queen of the Loo, Tilly, like Kate, became a local legend.  Also like Kate she was busted by the tax man in 1955, but her business struggled on and she ran brothels until 1968, by which time bigger, meaner and more dangerous criminals had taken over the game.

Tilly's 1925 mug shot for a razor attack
Tilly's 1925 mug shot for a razor attack

Tilly attended her arch rival’s funeral in 1964 but only outlived her by six years, dying from chronic bronchitis in 1970. 

And so it was, Sydney’s underworld was a women’s world, lorded over by two of Sydney’s most colourful ladies.  The girls ran the joint and they made sure that everyone knew.

On another note, as you all know History Week starts today.  If you want to get along to some events check out the program at historyweek.com.au. there is plenty of scandal, crime and corruption. 

A couple of events I spoke about this morning on Fbi are the City of Sydney’s free event at Customs House on Saturday 5th, Murder and Mayhem,  and for the more academically minded, next Wednesday 9th at Mitchell Library a full day symposium on scandals, crime and corruption  is being hosted by Macquarie University.

See you there.