… terrible retribution with gun, blade, or bludgeon which nowadays comes on swift, silent feet …

Truth (Sydney), 16 September 1928 

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.

Black & white dual mugshot, with man seated (left) and standing (right), with inscription.

John Daniel ‘Snowy’ Cutmore

(alias Harris, John McLaughlin, John Nolan, John Watson, Wilson)

5 July 1922

Suspect, offence unknown

Cutmore was a Melbourne-based tough who made forays into the Sydney scene when things grew too hot for him down south. He was a gunman, sly-grog seller and housebreaker with multiple convictions for assault. Cutmore’s death in 1927 was legendary. He was recuperating from the flu in bed at home in Melbourne when his enemy notorious gangster Squizzy Taylor burst through the bedroom door with a gun, intent on murder. Cutmore grabbed his own revolver and the two men shot at each other until Cutmore died, riddled with bullets. Taylor succumbed to his own wounds shortly afterwards.


  • Black & white dual mugshot, with man seated (left) and standing (right), with inscription.
  • Black & white dual mugshot, with man seated (left) and standing (right), with inscription.

Guido Caletti

16 July 1929 & circa 1930

Suspect, offences unknown

Sleek and self-assured, Caletti was a standover man and bludger (pimp) who robbed and assaulted his victims. He also acted as a pimp for his sometime girlfriend – Sydney’s most desirable prostitute, Nellie Cameron – and fought other bludgers who came sniffing around. It was rumoured that he could shoot the ash off a lit cigarette and throw a knife with unerring accuracy. Labelled a ‘gangster’ by police, Caletti was known to threaten witnesses, and few people were game enough to testify against him.


Black & white dual mugshot, with man seated (left) and standng (right), with inscription.

George ‘the Midnight Raper’ Wallace

18 April 1922

Suspected of attempted theft from a person

Wallace targeted the city’s sex workers, demanding a portion of their earnings and assaulting any who would not, or could not, pay up. Many prostitutes did not tell police about the assaults, fearing they would not be treated seriously and might be attacked again for talking. Wallace also dabbled in drug dealing and was said to be a cocaine addict. He sometimes worked with other bruisers, such as the infamous gunman Norman Bruhn and ‘Razor Jack’ Hayes; newspapers of the time christened the trio the ‘Unholy Three’.

Black & white dual mugshot, with man seated (left) and standing (right), with inscription.

Sidney ‘Kicker’ Kelly

(alias Patrick Kelly)

25 June 1924

Suspected of vagrancy

Kelly was involved in illegal gambling and drug distribution. He was handy with a gun, razor and his boots, for which he earned the moniker ‘Kicker Kelly’. He often worked with his brother Tom.