Underworld

Mugshots from the Roaring Twenties


15 Sep 2018 – 24 Feb 2019

  • Charles Passmore, 26 November 1928.
    Charles Passmore, 26 November 1928.
    Suspected of cocaine possession.
  • Kate Leigh, 2 July 1930.
    Kate Leigh, 2 July 1930.
    Suspected of cocaine possession.
  • Phillip ‘Phil the Jew’ Jeffs, 9 August 1922.
    Phillip ‘Phil the Jew’ Jeffs, 9 August 1922.
    Suspected of drinking in an unlicensed premises and being found in a premises frequented by thieves.
  • ‘Botany’ May Smith, 10 May 1928.
    ‘Botany’ May Smith, 10 May 1928.
    Suspected of supplying cocaine.
  • John Daniel ‘Snowy’ Cutmore (alias Harris, John McLaughlin, John Nolan, John Watson, Wilson), 5 July 1922.
    John Daniel ‘Snowy’ Cutmore (alias Harris, John McLaughlin, John Nolan, John Watson, Wilson), 5 July 1922.
    Suspect, offence unknown.
  • Guido Caletti, 16 July 1929 & circa 1930.
    Guido Caletti, 16 July 1929 & circa 1930.
    Suspect, offences unknown.
  • George ‘the Midnight Raper’ Wallace, 18 April 1922.
    George ‘the Midnight Raper’ Wallace, 18 April 1922.
    Suspected of attempted theft from a person.
  • Kong Lee, 27 November 1922.
    Kong Lee, 27 November 1922.
    Suspected of safe breaking.
  • Alex Westland Robertson (alias Alex Westland Mountbatten), 18 January 1923.
    Alex Westland Robertson (alias Alex Westland Mountbatten), 18 January 1923.
    Suspected of embezzlement.
  • Cameron McIntosh Bean (alias Clifford McIntosh Bennett), 24 March 1922.
    Cameron McIntosh Bean (alias Clifford McIntosh Bennett), 24 March 1922.
    Suspected of attempted bank robbery.
  • Gilbert Cochrane Burleigh (alias Gilbert Burley, Gilbert Burly, Gilbert Hawtree) & Joseph Delaney, 27 August 1920.
    Gilbert Cochrane Burleigh (alias Gilbert Burley, Gilbert Burly, Gilbert Hawtree) & Joseph Delaney, 27 August 1920.
    Suspected of false pretences (Burleigh); suspected of stealing in a dwelling (Delaney).
  • Olga Anderson (alias the Marchioness de Falaise), 11 November 1929.
    Olga Anderson (alias the Marchioness de Falaise), 11 November 1929.
    Suspected of blackmail.

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.

Meet the crims 

Bosses

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.

Bruisers

The brawn of Sydney’s underworld, bruisers had a penchant for senseless violence. Some were independent operators who collected cash by intimidating owners of various legal and illegal businesses, from greengrocers to sly-grog shops. Others worked for crime bosses as bodyguards and debt collectors. The tools of their trade were revolvers, cutthroat razors, and their fists and feet. Many bruisers met violent ends.

Petty Crims

Petty criminals made up the largest group of felons and committed a diverse array of crimes, ranging from stealing to using offensive language. Few people crossed the path of a crime boss but many would have met a petty criminal. They were the reason people bought home insurance, avoided dark alleys and balked at offers that seemed too good to be true. Small-time crooks were constantly on the lookout for new opportunities and targets, and their activities kept police busy.

Plotters

Parting fools from their money was the plotter’s goal, and took careful planning and superior powers of persuasion. Plotters each had their own speciality, ranging from organising complex bank robberies to deceiving a drunk with a sleight-of-hand card trick. Many plotters possessed charisma and could play a part to perfection.