The underworld is a society in itself, and a society which knows sterner laws of caste and position than the social world of any of the great cities of the world.

Truth (Sydney), 26 October 1924

The Roaring Twenties was a golden era for criminals. Social change post World War I brought opportunity, especially for the criminal elite. New markets emerged that could generate incredible wealth for those willing to operate outside the law. In Sydney, the strongest and most cunning criminal bosses monopolised the sale of illicit drugs and drink, employing toughs to protect their interests, clever crims to devise new scams, and weaker ones to do the drudge jobs.

The crime bosses and their gangs carved up the inner city into mini empires. As transport options improved, the middle classes moved away from the centre, leaving inner-city suburbs of multi-level terrace housing to fall into disrepair – and disrepute. Densely populated Surry Hills became Kate Leigh’s heartland, brothel madam Matilda ‘Tilly’ Devine dominated the slums of East Sydney, and ‘bludger’ (pimp) and sly grogger Phil Jeffs’s territory spread across Darlinghurst (nicknamed ‘Razorhurst’ following a number of razor attacks) and later into the central business district. Turf warfare frequently erupted between established and aspiring bosses over control of vice and drugs in these downtrodden areas of the city.

Perhaps curiously for people living such chaotic lives, criminals created their own strangely rigid power structure. The hero of the 1920s was the successful bank robber – ballsy, armed and dangerous. At the bottom of the pile were those who preyed on children and the elderly. Featured here are four categories of felon – bosses, plotters, bruisers and petty crims.