Underworld: Mugshots from the Roaring Twenties



Meet the bosses

The plotters

The bruisers

The petty crims

Descend into the 1920s underworld in the new photographic exhibition revealing the dark side of the Roaring Twenties.

See the players of Sydney's criminal underworld and the police who fought to keep the mean streets clean through more than 130 candid and compelling mugshots taken by police between 1920 and 1930.

Meet all the players at Underworld: Mugshots from the Roaring Twenties

15 September 2018 to 24 February 2019


Exhibition information

The Roaring Twenties

The 1920s heralded the brave new world that emerged from the devastation of World War I. Australia’s allegiance to the British Empire’s war effort had come at a high price: thousands of young men had been slaughtered, families had been dislocated, and returned soldiers often struggled to fit back into the rhythms of society. Similar stories played out in other countries around the globe. Eager to put the horror and drudgery of war behind them, people began rebuilding their lives.

The Roaring Twenties saw dramatic changes in technology, entertainment, architecture and society. Young women sought new freedoms, movies began influencing the way people lived, and technological developments such as faster, more reliable motor cars improved the lives of millions. Change brought opportunity, and criminals around the world found ways to cash in on developing illegal markets. Police forces, their numbers reduced by war, were caught out. Their work was made harder by the fact that laws did not always keep up with the pace of criminal evolution.


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 Jeff'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.


Sydney’s police force had lost many men on the battlefields of France during World War I and it took some time to rebuild; in 1920, the Commissioner of Police testified that the force was between 200 and 300 men short of the number needed to do the job effectively. With resources stretched, police struggled to maintain law and order in an environment where criminal behaviour was evolving.

Rapid changes in society created opportunities, especially for the criminal elite, and generated new challenges for police on the beat. New illicit markets emerged in the Roaring Twenties that could generate unbelievable wealth. The highly profitable sale of illegal alcohol (‘sly grog’) attracted international organised-crime groups to Australia, with members of the Mafia-like Camorra involved in the trade alongside home-grown cartels. Policing unlawful drug use was also a growing problem in Sydney, although it was not until 1928 that two officers were assigned full-time to the Drugs Bureau. The growing number of vehicles on city streets created more work due to an increase in vehicle theft, joy-riders and speedsters. Dishearteningly for officers, the law did not always keep pace with the changes in criminal behaviour.

Image credits (in page order):
Arthur Caddy, 6 March 1929.
Olga Anderson (alias the Marchioness de Falaise), 11 November 1929.
Augustine ‘Gus’ Gracey (alias Charles Augustine De Gracie, Charles August De Gracie, Charles August Deane) and Edgar ‘Eddie’ Dalton (alias Adamson Mitchell), c1920. 
Kate Leigh, 2 July 1930.
NSW Police, Forensic Photography Archive, Sydney Living Museums.

Event Details

15 September 2018 - 24 February 2019
Free with Admission

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