Sydney’s underworld bosses were tough, resolute and violent – mess with one and you would know you had been in a fight.

Many had spent time in juvenile justice homes, where they made contacts who helped them to graduate to bigger and nastier crimes. They then rose up from the ranks to create their own empires. Having clawed their way to the top, they jealously guarded their turf and employed ‘staff’ to do their dirty work. Most bosses were entrepreneurs who changed their rackets from opium to sly grog to cocaine as the illicit markets shifted. All generally adhered to the same criminal code – always shoot first.

Charles Passmore

26 November 1928
Suspected of cocaine possession

Known to police as the ‘King of the Underworld’ and to media as the ‘Cocaine King’, Passmore, like many other bosses, had a lengthy and diverse criminal record, with convictions for fraud, theft, selling sly grog, dealing cocaine, and armed robbery. He employed a gang of low-level criminals, including at least one American armed robber and a disabled returned serviceman who was a street dealer for Passmore’s cocaine empire. Police considered Passmore a criminal mastermind, and indeed he showed great acumen as he reshaped his business to fit new illicit markets. In 1929, he was convicted of taking part in a robbery during which two bank employees were shot and wounded. He was sentenced to 12 years’ prison.

Kate Leigh

2 July 1930
Suspected of cocaine possession

Leigh was known as the ‘Queen of the Underworld’. She was a bold felon who reigned over the majority of Sydney’s sly-grog market before adding cocaine distribution to her portfolio of illegal activities. Reputed to have had a punch like a kick from a mule, she ran her empire on her own terms, hiring men to assist her but always maintaining sole control of the businesses. Fellow boss ‘Chow’ Hayes said, ‘If you were sweet with Kate, she’d do anything for you and give you anything. But if you crossed her, she’d shoot you’ (David Hickie, Chow Hayes: gunman, Angus & Robertson, Sydney, 1990).

Phillip ‘Phil the Jew’ Jeffs

9 August 1922
Suspected of drinking in an unlicensed premises and being found in a premises frequented by thieves

Jeffs was involved in various rackets, including sly grog, theft, prostitution, cocaine and illegal gambling. Known as a gunman early in his career, he later cultivated a more refined reputation by setting up nightclubs that sold sly grog to a better class of customer. He reputedly had many influential friends in business, politics and the police force. Jeffs made a lot of money from crime; during the Depression of the 1930s it was common in Sydney for a wealthy person to be described as being ‘as rich as Phil the Jew’. He also made a lot of enemies. He was shot during a gang war in 1929 but recovered from his wounds. Following the criminal honour code, Jeffs told police he could not identify his assailant.

‘Botany’ May Smith

10 May 1928
Suspected of supplying cocaine

Smith was known as ‘Botany May’ because she once lived in the industrial suburb of Botany in south-eastern Sydney. However, she operated her businesses out of a Surry Hills terrace, from where she ran a brothel, fenced stolen property and, later, supplied cocaine to some of Sydney’s second-tier drug dealers. She was clever, cunning and violent. Constable Lillian Armfield, one of Australia’s first female police officers, once knocked on Smith’s door then kept it open for fellow officers as part of a police raid. In response, Smith ran to the back of the house, grabbed a red-hot flatiron off the stove and chased Armfield. The Surry Hills house was often under police surveillance, as many of the city’s petty criminals were known to frequent the property.

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