True (crime) love: Australian’s criminal crushes

Is it our convict past? Those romantic bushranger years? Maybe it’s the celebrated Australian contempt of authority and our fair-go attitude. Whatever the reason, we serially, seriously crush on people who have found themselves on the wrong side of the law. We have a collective case of bad boy (and less frequently, girl) syndrome.

Not all criminals are qualified to become celebrity crims: a sense of style and a certain ‘to hell’ attitude seem to be required. Here are some low-life Aussies who we know we should deplore – but can’t help having a bit of a soft spot for.


Ned Kelly: Australia’s first criminal crush

No account of Aussie outlaw love can avoid beginning with Edward ‘Ned’ Kelly, our first celebrity crim. The son of an Irish convict who was transported to Australia for selling two pigs, Kelly turned to crime when he had to support the family after his father committed suicide after a stint in jail for a similarly trivial crime of poverty – the perfect backstory for a budding folk hero. Even during the 1870s when he and his gang were robbing banks and committing hold-ups around north-eastern Victorian, he garnered admiration for standing against a police force who supported and enforced of the despised squattocracy.

But what really kept Ned’s image alive was his knack for publicity and a fine sense of theatre. His ‘Jerilderie Letter’, a 56-page document justifying his crimes and identifying with oppressed Irish Catholics and the poor of Victoria, made him an instant good guy. His genius (if ultimately ineffective) suit-of-armour move, as well as the fact he paid the ultimate price for his crimes, ensured his role as Australia’s favourite outlaw and fuelled countless tributes in song, art, film and epic tattoos.


Squizzy Taylor, the Underworld Dandy

Joseph ‘Squizzy’ Taylor was one of the first but certainly not the last of our homegrown thugs to introduce some Stateside glamour. A short man with an oversized attitude, he modelled his style on the Prohibition-era bootleggers of the USA, dressing like a toff, flaunting diamond-studded jewellery and sporting gold teeth. Getting off to an early start in crime – his first arrest was at the age of 17 for ‘insulting behaviour’ – he soon graduated to pickpocketing and minor theft. By 1916, he was suspected of two murders, though neither could be pinned on him.

Squizzy made his name during the Fitzroy Vendetta, a violent gang feud that tore up Melbourne’s seedy inner suburbs in 1919. Through the 1920s he was a race-fixer, racketeer, armed robber, drug-dealer, and criminal all-rounder known by some as ‘The Underworld Dandy’ for his OTT dress style. His confident, dapper flamboyance, as well as his incredible luck at escaping conviction at his many trials (also on his criminal CV: jury-rigging) kept him in the headlines until his violent and predictable death in a gangster gunfight in Carlton in 1927.


Kate Leigh, ‘the worst woman in Sydney’

While Melbourne gangsters were shooting up a storm, in Sydney gangs were slicing each other up with cut-throat razors in an unintended consequence of the banning of handguns. Six-o’clock closing, the prohibition of street prostitution and the recent ending of the sale of cocaine by chemists had opened up a plethora of career opportunities for the budding crim. Into the limelight stepped Kate Leigh, a teetotaller who at her peak is thought to have run 20 sly-grog joints (with a sideline in cocaine trafficking) around Surry Hills.

She also headed up one of the biggest and most deadly of the ‘razor gangs’ that terrorised the city from 1927 to 1931. Her nemesis was fellow underworld queen, bootlegger and madam Tilly Devine. One can only assume Tilly was miffed that it was Kate who the gobsmacked Sydney press dubbed ‘the worst woman in Sydney’. The city’s leading sly-grogger through the 1930s and 40s, Kate was a larger-than-life figure described as both matronly and vicious; flamboyantly wealthy, she often showed up to court dressed to the nines with a diamond ring on each finger. She passed away peacefully in 1964 at the age of 82, in the Surry Hills flat that was once her main booze dispensary.


Mark ‘Chopper’ Read: criminal raconteur

Australia’s first modern celebrity thug, Mark Read’s career is an uncomfortable mix of extreme violence, wild literary success and sick folk-hero-dom. He began by robbing drug dealers, and moved on to torturing underworld crims – removing their toes with bolt cutters was a speciality. Between the ages of 20 and 38, he spent just over a year outside of prison, serving sentences for armed robbery, assault, arson, impersonating a police officer, and plenty more.

A confessed multiple murderer (he once claimed to be involved in the killing of 19 people, but that’s completely unreliable as he’s made countless contradictory statements and confessions), it’s Read’s post-criminal life as a media superstar that makes him stand out. However disgraceful a human being he was, Read was a gifted raconteur – his first book of prison anecdotes, 1991’s Chopper: From the Inside, sold over 200,000 copies, and he continued to pump out memoirs (no doubt highly embellished) over the years. He became a one-man publishing empire – he even wrote as book for kids – inspiring the archetypal handlebars-and-tatts criminal look, launching Eric Bana’s film career, and kick-starting the queasy fascination with grungy local true-crime that has brought us seemingly endless parade of Underbelly TV shows. Thanks, Chopper!


Brenden Abbott, the Postcard Bandit

While Brenden Abbott had a successful career in armed robbery, the most glamorous of crimes – he’s believed to have made off with around $5 million in total, little of which has ever been recovered – it’s his daring escapes and life on the run that brought him criminal celebrity.

Most famously, in 1989 he escaped from Fremantle Prison (a one-time event in its 150 years) in a homemade prison guard uniform. He went on to spend 5½ years on the lam, earning the title of Australia's Most Wanted, and serially eluding (and humiliating) police using clever disguises, fake IDs, and safehouses. The postcards are a myth, but photos emerged of an Akubra-sporting Abbott clearly enjoying his life as a fugitive from justice.

After being recaptured in 1995, Abbott escaped again from a Queensland prison in 1997; this time in a hail of gunfire after cutting through cell bars and perimeter fencing. After being recaptured in 1998 after a shorter stint of freedom he was sentenced to 23 years in prison. According to his supporters, the length of his sentence is due to to his serial shaming of the authorities rather than any real threat to society. He’s eligible for parole in 2026 – unless he breaks out first.

Main image: Ned Kelly (Charles Nettleton, State Library of Victoria)

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