The world of organized crime is often thought of to be a man’s world. Characters like Bugsy Siegal, Al Capone and Pablo Escobar are all names synonymous with organized crime; simultaneously despised and revered for their cutthroat business practices and their criminal activities. Women often did not have much of a place in the criminal underworld and if they did, then they were more than likely high-ranking prostitutes at best. That was not the case in the suburbs of Sydney, Australia.

After the death of a high ranking crime boss, two women – Tilly Devine and Kate Leigh – wanting total control over New South Wales Australia’s criminal underground, were some of the most ruthless gangsters the country had ever seen.

Tilly Devine

Tilly Devine

Tilly Devine

“The Queen of Woolloomooloo” got her start as a prostitute, working her way up to brothel madame. By 1927 Devine owned a number of brothels around the Sydney suburb of King’s Cross. Catering to clientèle ranging from high-ranking politicians to factory workers, Divine had a stronghold on the prostitution trade within the area.

Even before she rose to the top of the sex trade, Devine had a rap sheet as long as her arm. Her offenses included prostitution, indecent language, assault and offensive behavior. In 1925, Devine was sent to prison after slashing a rival prostitute in the face with a razor blade. It was then that she decided to leave the life of a streetwalker behind and began opening her own brothels upon her release.

Exploiting a loophole within the law stipulating that only men could not profit from prostitution, Devine was able to quickly dominate the sex trade undisturbed by law enforcement officials. The law enforcement that did attempt to intervene on Devine’s operations were bribed and sent away. It would seem that no one could stop Devine and it wouldn’t be long before she became one of the richest women in Sydney.

Kate Leigh

Kate Leigh

Kate Leigh

After legislation was passed to prohibit alcohol sales after 6pm, unlicensed bars known as sly grogs began popping up around Sydney. Kate Leigh was already an entrepreneur in illicit sales by that time, with her hands in everything from drug sales to the sex trade, but it would be her sly grogs that would gain her the title as “Queen of the Underworld.”

Leigh was always surrounded by male gangsters for protection purposes, but it was often Leigh who would be forced to protect them from rival gangs. Swift with a pistol and an unconvicted murderess to boot, Leigh was one woman even the most ruthless male gangsters didn’t want to mess with.

Though she was able to beat her murder charges, Leigh was well acclimated with the criminal justice system. Arrested 107 times and jailed for 13 of her offenses, Leigh was known to show up to court wearing her finest furs and diamond jewelry, as if she were trying to send the message that even jail could not stop the other richest woman in Sydney from continuing to rule over her criminal empire.

The Razor Wars

For nearly 20 years both Leigh and Devine’s gangs engaged in constant wars, with the women even personally fighting one another on a number of occasions. Both women wanted complete dominance over Sydney’s black markets and would stop at nothing to get it. When not involved in physical altercations, both women were known to turn to the media in order to present themselves as upstanding business women, while simultaneously slandering the name of the other.

In 1927, New South Wales passed legislation restricting concealed weapons. As a result, many gang members stopped carrying guns unless there was important business to settle and instead began carrying razors for the potentially disfiguring scars they would leave upon an intended victim. These gangs became known as razor gangs, and both Leigh’s and Devine’s were known as the biggest and baddest of them all.

In an early war between the gangs, an altercation between one of Devine’s men and one of Leigh’s guys led to a shootout at Devine’s home. Devine’s then husband, “Big Jim”, walked out of the door and shot three of Leigh’s men, including a man whom had been her lover at the time. For the two years that followed, the streets of Sydney ran red with blood as a result of the feud between the women.

That feud would come to a head in 1939. Known as The Battle of Kettle Street, Devine and Leigh’s gangs rioted in the streets for over an hour. High on cocaine and liquor, the gangs attacked one another with guns, razors and empty bottles. By the end of the battle, most of the members involved in the fight were hospitalized for serious injuries.

In 1930 New South Wales police were forced address the growing concern over the razor gangs. Harsh penalties were imposed for those even seen speaking with someone with a criminal history. Though the clamp down may have reduced the gang violence associated with the women’s respective empires, both Leigh’s and Devine’s businesses still thrived.

The Tax Man Cometh

Kate Leigh posing with Tilly Devine

Kate Leigh posing with Tilly Devine

The law may not have been able to catch up with Leigh or Devine, but there was one man who could. The tax man.

Both women were known to be the wealthiest in all of Sydney, but had failed to pay taxes on most of their illegally procured funds. In 1955, the Department of Taxation ordered Devine to pay over £20,000 (roughly $28,000 at today’s exchange rate) in back taxes. Devine was forced to sell off her brothels and other real estate she had owned in and around King’s Cross. She was nearly bankrupt, but continued to run her remaining brothels until 1968.

Kate Leigh wasn’t as lucky. In 1954, years of unpaid taxes resulted in the Taxation Department seizing most of her assets. Her sly grogs were beginning to shut down once New South Wales reformed the law to allow for bars to serve alcohol until 10pm, leaving her with only her legitimate hotels before the Taxation Department took what was left. With little income coming in, Leigh was practically penniless and living in a small room above one of the hotels she once owned. She was financially dependent on her nephew until she died of a stroke in 1964.