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The Police Commissioner Made A Deal With Leigh And Devine. In 1935, Police Commissioner McKay decided to speak with Devine and Leigh to get them to stop ordering attacks and cut the cocaine distribution. It was either they stop picking on each other and pedalling coke, or the entire police force would find a way to shut down every shady business they both had. So they agreed.

Tilly Devine ‘Queen of Woolloomooloo’


Kate Leigh “Queen of the Underworld”

Brothel Madams to Crime Moguls: These Women Terrorised Sydney with Their Fierce Gang Rivalry. Dubbed the “Worst Woman in Sydney,” Tilly Devine was the Queen of the criminal underworld in Woolloomooloo in the 1920s. She spent years as a prostitute and ran a string of brothels, in addition to heading a razor blade gang.

Not far behind her in the criminal ranks, was rival razor gang leader and booze bootlegger Kate Leigh. Leigh was the Queen of Surry Hills, but she had her eye on becoming the crime lord of Sydney and would stop at nothing to dethrone Devine. In addition to terrorising Sydney, the two would have brawls in the streets and attack each other’s businesses.

Tilly Devine was born Matilda Twiss and began her career of prostitution as a teenager in England. She didn’t take on the name Tilly Devine until she met Jim Devine, an Australian serviceman, in 1917. She married him and followed him back to Australia in 1919, where she managed to accrue 79 convictions in just five years time. It wasn’t until 1925 that any of her arrests resulted in a serious penalty—she served two years jail time after slashing the face of a Sydney Corke with a razor blade.

Tilly Devine had extensive criminal history including assault, carrying razors, shooting with intent, prostitution, offensive behaviour and indecent language.

When you think of the 1920s underground crime culture, you probably think of something akin to ‘The Godfather’. Suave men in suits, quick talking and big rolling who are happy to take down one of their rivals with the nod of a head and the pull of the trigger. While Sydney’s history does not boast as much of a reputation as the gangs of New York or the Five Point Gang, that doesn’t mean nothing was going on.

While Al Capone owned the streets of the Big Apple, Tilly Devine and Kate Leigh were fighting it out on the streets of Sydney in the Razor Wars.

Tilly Devine, after moving to Sydney quickly became acquainted with breaking the law. By the beginning of World War II, the Devines had procured a large string of brothel businesses in Woolloomooloo. She became notorious in the papers and was dubbed ‘Queen of the Loo’. Placing her in just the right spot to garner a rivalry with… Kate Leigh. A queen in her own right, the ‘Queen of the Underworld’ was Sydney-born and owned the streets of Surry Hills. Leigh and her husband were known to the police from a young age, and slowly gained an empire of sly liquor establishments. For protection, she aligned herself with some of the greatest gangsters that Sydney had to offer. This would later become useful when the Razor Wars began in 1927.

Profits from their criminal enterprises put them among the city’s wealthiest citizens. Tilly and Kate,  ruled the traditionally male-dominated world of inner-Sydney crime because they were more ruthless, more violent and smarter than the guys. Each notched up about 150 convictions and served more than 30 prison terms.

After the pubs closed at 6 pm, Kate – who wore a floppy, wide-brimmed hat, dangling ostrich feathers and, like Tilly, furs and flashy rings – sold alcohol, cocaine and stolen goods in a score of sly grog shops in Surry Hills, Kings Cross, Woolloomooloo and Darlinghurst. Both had a volcanic temper. Many of their arrests were for assault. Tilly fought with Kate and rival crooks, her husband and henchmen, and innocent passers-by who dared to look at her too long.

When hoodlum Snowy Prendergast invaded Leigh’s home at 104 Riley St, East Sydney, on March 27, 1930, and laughed at her when she demanded that he leave, she shot him dead.

Devine became a wanted crime lord — working as both an infamous thief, drug dealer, and a legal owner of most of the bordellos in Sydney. Ironically enough it was stricter laws that allowed both Devine and Leigh to flourish, drastically increasing their finances and power. They made the transition into madams after street prostitution was prohibited in 1905 and men were banned from profiting from brothels. Both women could run brothels and profit off other sex workers.)

Devine became one of the richest women in Australia, known for buying luxury cars and jewellery, and allocated a portion of her wealth to buy off authorities. Despite being prone to violence and jailed innumerable times for prostitution, drugs, and even attempted murder, she also built a reputation for being charitable.

Devine was dubbed the ‘Worst Woman in Sydney’ and after years of working as a street-walking prostitute, she had her first prison stint in 1925 after slashing a man’s hand with a razor until ‘blood squirted in his face’.

‘I never said a word. She said “There he is, the b*****d,” and swung her arm and I put my hand up to my face and I felt the sting then saw blood,’ victim Sydney Thomas Thornton Corke said in a police report.

Devine, who was known as ‘Queen of Woolloomooloo,’ ran a string of brothels after working for years as a prostitute. She served two years in Long Bay prison for slashing a man’s hand with a razor until the blood ‘squirted in his face’

Her rival, Kate Leigh – known as the ‘Queen of Surry Hills’ ran an alcohol business which illegally sold alcohol after 6 pm. Leigh and Devine would often send gang members to trash their businesses and tattle on each other to police.

The pair of women, who headed two of the most powerful rival ‘Razor’ gangs in the 1920s, were largely considered the Queens of the city as they battled for control of Sydney’s criminal underworld. To protect their interests, each woman employed a ferocious gang whose members armed themselves with razors after the Pistol Licensing Act of 1927 ordered long jail terms for anyone caught with an unlicensed revolver. Tilly and Kate’s inner-east Sydney stamping ground became known as “Razorhurst”.

Though their criminal activities rarely overlapped, Tilly and Kate despised each other. Each longed to be Sydney’s undisputed crime boss with all the wealth, power, fear and headlines that status guaranteed. In the Leigh-Devine gang war, which was ended only by the consorting laws of the early 1930s forbidding criminals to meet in public, at least six were slain and hundreds were slashed and otherwise wounded.

The war between the two women began in the late 1920s for a number or reasons, primarily the outlawing of prostitution, cocaine and the closing of bars and hotels at 6 pm. The razor became the gangster’s weapon of choice after the requirement to license pistols was introduced in 1927. The straight barber’s razor was effective on the throat and easy to conceal, making it the perfect weapon.

From 1927, the violence in Sydney rumbled, slowly escalating with murders that no one was charged for. At least, this was the case until 1929 at the ‘Battle of Blood Alley’. This riot in May led to a larger riot in July, played out from Woolloomooloo all the way to Tilly Devine’s Maroubra home. Two of Tilly’s men were attacked by a group of Kate’s associates one evening. As they followed the men back to Devine’s home, Tilly’s husband managed to shoot dead one of Leigh’s right-hand men, yet was never charged with the murder. In early August, Devine got her revenge on Leigh, attacking one of her businesses in what became known as the ‘Battle on Kellett Street’.

Nellie Cameron (pictured) had many relationships with gangsters and became known as the ‘kiss of death girl’.

In the 1920s and ’30s, the East Village Hotel was ‘the Tradesman’s Arms’, a blood house with sawdust on the floor to soak up the spit and vomit, hard stools at the bar and a dozen cheap wooden tables and chairs scattered around. The air was thick with coarse language, raucous laughter and the cigarette smoke pumped out by the Arms’s clientele – the factory workers and bakers from the nearby Sergeants pie factory, prostitutes, pimps, pickpockets, muggers, con men, SP (starting-price) bookies and drug dealers. Cards and two-up were regularly played in the back bar. Fights erupted regularly. Tilly Devine called in to transact business, since the Arms was in the heart of her red-light stomping ground, and just across the street from the brothel and sometimes home at 191 Palmer Street. Nellie Cameron and Frank Green were also regulars.

Devine, who was born in England in 1900 as Matilda Twiss, began working as a prostitute after leaving school.

After working as a prostitute for ten years Tilly capitalised on the astounding anomaly in the Offences (Amendment) Act of 1908 that made it illegal for a male pimp or brothel-keeper to profit from the immoral earnings of prostitutes but not for a woman to do so. She became a madam, using the money she had salted away to bankroll the biggest, best organised, most lucrative brothel network Sydney has ever seen.
In her employ were prostitutes of every age and background. Big Jim sold cocaine to his wife’s prostitutes. It made economic sense for brothel-keepers like the Devines to foster drug addiction in the sex workers: it ensured loyalty and meant prostitutes increasingly preferred payment in cocaine rather than in cash.

Tilly Devine was on her way to becoming the woman about whom it was written in a police article at the end of her 204th conviction criminal career:

She has been in conflict with society all her life. She has fought it with words, with action, and with her bare hands. She has held it by the throat and shaken it. She has spat in its face. Her sense of values, her code of morals and of ethics, are her own and she well tolerate no interference. For the average man, her life had held that singular fascination the criminologist describes – the fascination of the thunderstorm.

In her employ were prostitutes of every age and background. Seasoned streetwalkers who’d been operating since before the war, hard-up housewives and mothers from the suburbs trying to support their families, lonely and poor young women who had come to the city from the country, or inner-city street kids drawn by danger and excitement and the chance to make more money than they could be working in a factory or shop. Tilly was regarded as a benevolent despot by her workers. If they did their job she pampered and protected them. But if she caught her ‘girls’ cheating her, she’d sack them – and often beat them as a parting gift.

Devine and Leigh began collecting men to help protect their businesses. Their weapon of choice were razors—they were cheap, easy to carry, and the punishment for carrying handguns was too steep. The competition between the two crime queens led to their razor-wielding gangs randomly attacking each other in the streets on a regular basis. They organised attacks as well, and the gangs were sent out to trash the rival brothels and grog shops. They even went so far as to drag the police into it, each playing the victim and ratting out the other gang.

Devine owned this three-bedroom home in the Sydney East suburb of Maroubra and hosted many gangster parties.

Violence between the gangs was at a head in the 1920s, with a personal enmity growing between the two ladies. Their henchmen would often attack one another if they saw each other in the street and Leigh and Devine would send their people to trash each other’s brothels and grog shops. Afterwards, they’d tattle on each other to the police.

The ladies were not above violence themselves. In 1929  Devine had an altercation with one of Leigh’s friends, Vera Lewis. The paper added that “Lewis alleged that Devine scratched her…and getting her teeth on her little finger would not let go until the police intervened.”

Despite her violent ways, Devine’s life was going well. She’d made substantial investments in real estate and became known for her finery, Pomeranians and fabulous parties. Leigh, too, was famous for her fur and diamonds, financed by her thriving grog trade. The money, allegedly, was not all going on herself, however. After Leigh ended up back in court for more criminal behaviour, the Barrier Miner reported on a softer side of the Sydney Queen, commenting that a detective who followed her one day “found her bound on a noble errand of supplying food to unemployed.”

The streets of Sydney were booming with violence in the 1920s—so much that the police cared more about the violence than any of these women’s other illegal activities. They could deal with the booze and the prostitution, but they couldn’t stand the chaos on the streets. Laws were enforced to kerb gang association and strict punishments for those caught carrying razors was established. In 1935, Police Commissioner McKay decided to speak with Devine and Leigh to get them to stop ordering attacks and cut the cocaine distribution. It was either they stop picking on each other and pedalling coke, or the entire police force would find a way to shut down every shady business they both had. So they agreed.

Devine expanded her business ventures into real estate investments, threw lavish parties often, and surrounded herself with Pomeranians. Leigh was thriving as well, dripping in diamonds and fur, and still found it in her heart to supply the poor with food. Both women were social, patriotic, generous towards the less fortunate, and had softer sides shared only with loved ones.

Kate Leigh had bigger aspirations than owning a string of brothels. Again, laws led to immense profit. Between 1906 and 1927, cocaine and horse betting became illegal and bars were forced to close early. This created three voids she was able to fill. Leigh organised her girls and had them selling cocaine and illegal bets on the streets. Then she opened ‘sly-grog’ or bootleg liquor establishments and watched the money pile in.

Devine and Leigh (pictured) headed two of the most powerful rival ‘Razor’ gangs in the 1920s, were largely considered the Queens of the city as they battled for control of Sydney’s criminal underworld.

In 1916, after a riot by 5,000 pub-crawling Anzacs outraged the public, Premier William Holden called a state of emergency and closed Sydney’s pubs. This was the beginning of the ‘Six O’Clock Swill’. Anybody thirsty after dark had to look elsewhere.
Kate Leigh took advantage of the huge market and for thirty-five years provided illegal liquor, known as ‘sly grog’. At the height of her career, Kate ran more than twenty sly-groggeries. Some of her sly-grog shops were upmarket and frequented by businessmen, others said police, ‘catered to the worst class of thieves and prostitutes’. On Friday and Saturday nights, crowds of men milled in the street awaiting admittance to ‘Mum’s’ as her establishments were known. The home got its nickname ‘mum’s’ from the passcode of calling around ‘to see Mum.’

Her main dispensary was a flat above her fruit-and-vegetable shop at 212 Devonshire Street, where she remained until her death from a stroke on 31 January 1964, aged eighty-two.

From the early 1920s until the ’40s, Kate Leigh, as Sydney’s leading sly-grogger and with her income protected by her own combative nature and a team of bashers and gunmen, was one of the wealthiest, and most flamboyant, Sydney-siders. Larger than life, greedy, funny when she felt like it and vicious when she needed to be, Kate was like a twentieth-century Long John Silver, a pirate captain aboard the Jolly brig Surry Hills. Aside from running the groggeries, she was a standover merchant, a dealer in drugs (for a while she was known as ‘the Snow Queen’), a fence for stolen property and, more for sport than anything else, a deft shoplifter. By the mid-’20s, the newspapers would be calling her the ‘Most Evil Woman in Sydney’.

Ms Leigh was a flamboyant and sometimes vicious character who by the mid-1920s was dubbed ‘the most evil woman in Sydney.’ Although she never drank alcohol or took drugs, Ms Leigh happily dealt in both and acted as a stand over merchant, sold stolen property and occasionally shoplifted. From the early 1920s to the 1940s, men crowded the streets outside her establishments at nightfall on Friday and Saturday nights to gain entry and purchase alcohol.

Kate Leigh the sly grog queen and her criminal rival, brothel madam Tilly Devine pretend to be friendly but theirs was a bitter relationship. Business Was Booming For Both Women, They certainly didn’t need to lash out at each other or compete for business. Their brothels were booming during the Second World War, there were plenty of servicemen for each woman’s business. U.S. troops were more than happy to buy their beer and spend an evening with their women. But after the war, their businesses dwindled.

From the NSW Police Force Archives:

No more remarkable woman ever strode upon the stage of Sydney’s nightlife than this middle-aged, matronly dame who slinks a furtive figure in the background of the drama of real life. A sinister, shadowy character, she plays a dominating part in the tragedy which is spelt D-O-P-E. She meets young women in cafes and hotel lounges, and she ingratiates herself with them. Such a nice, agreeable dame! Such a monster in human disguise. For she deals in a commodity that means more than the wrecking of physical health. It means the destruction of mental health, the warping of the moral outlook, the damning of the eternal soul. Clever and unscrupulous enough to know that once a victim is made, she becomes a sure customer for life. To show them the door to Drugland she paints a glowing picture of the joys inside. She conjures up hours of gay, exotic happiness. They open the door, slowly, hesitatingly. She stands behind them and reassures. They enter and find – a living hell. Price is nothing to the victims. They will pay all that is asked. They want more and more and more. If it gets too dear for them, they stop at nothing to get the money. They will impose on their friends, they will steal and descend as low as a woman can to feed the ravenous appetite that dope creates. It is a tragic but terribly true thing a great percentage of fallen women who walk the pavements of Sydney are drug-takers.  

Devine was dubbed the ‘Worst Woman in Sydney’ and after years of working as a street-walking prostitute, she had her first prison stint in 1925 after slashing a man’s hand with a razor until ‘blood squirted in his face’ (pictured is the victim’s police statement)

Kate Leigh, pictured at her 2 Landsdowne Street, Surry Hills house with her second husband, sly grog dealer Teddy Barry dressed as Santa Claus for one of their generous Christmas gift givings.

The outdoor toilet at the back of Kate Leigh’s property where thieves and prostitutes bought illegal alcohol after it was banned, allowing a flourishing trade in sly grog.

In the 1920’s, the streets of Sydney ran with blood as a pair of criminal empires went to war, armed with razors. The most famous of the violent clashes became known as “The Battle of Blood Alley,” but perhaps what is most surprising about the gang wars was that the leaders of the rival empires were both women. Tilly Devine and Kate Leigh spent years battling for control of booze, drugs and prostitution on the streets of Sydney, and during their reign as Queens of their domains, they both became rich, but not without the crimson stain of blood on their manicured hands.

Tilly used the proceeds from her brothel to spread out into other criminal activities, and while she was convicted 204 times, and spent much of her time in jail, she managed to amass a huge fortune, a chunk of which she poured into Sydney real estate ventures. The Devine’s massive fortune was legendary among the citizens of Sydney, as was the vicious nature of her husband Jim, who was tied into a number of high profile murders, yet somehow always managed to escape conviction based on pleas of self-defense. The pair had a tempestuous relationship, and at one point Jim tried to shoot his wife to death, but she was able to dodge the bullets that were intended for her.

The marriage eventually reached its conclusion in 1944, by which time the business was in its first stages of decline Tilly was nailed with a huge tax bill in 1955, but claimed that she had more money and jewels than she knew what to do with, and was able to remain in business until 1968, when she finally sold off the last of her brothels. Tilly passed in 1970, and by that time the tales of the infamous razor wars of the late 1920’s were beginning to slip into the annals of history, as was her legendary feud with cross-town criminal rival Kate Leigh.

The pair pitched had their gangs pitch running battles in the streets, with the razor attacks prompted by the Pistol Licensing Act 1927, which outlawed the carrying of handguns. The razors were particularly effective when it came to disfiguring the rival prostitutes, and by the time the worst of the fighting had passed, it was believed that more than 500 people had fallen victim to death or injury by the barber’s blade. Leigh and Devine were not above the fighting, and on more than one occasion the pair clashed in the street in violent brawls.

A police document reported a ‘blood-stained’ razor was discovered in the gutter near Ms Devine’s Surry Hills home on Crown Street, linking her to the crime.

Although she never drank alcohol or took drugs, Ms Leigh (pictured) happily dealt in both, acted as a standover merchant, sold stolen property and occasionally shoplifted. Ms Leigh was a flamboyant and sometimes vicious character who by the mid-1920s was dubbed ‘the most evil woman in Sydney.’

Kate Leigh had a reputation as a woman not to be messed with, and where many of the more successful Madams required protection from gangs, she was more often the one that did the protecting of them. Born in 1887 in Dubbo, NSW, Kate Leigh suffered from serious neglect at the hands of her parents, which landed her in a girls’ home by the time she was 12. She also gave birth to her first child at the tender age of 13, and by 15 was on the first of her three marriages. It’s believed that her rough upbringing, and introduction to adulthood at such a young age, was what brought about her steely resolve.

Much like her bitter rival Tilly Devine, Kate used the loophole in the law to become the Madam of her own brothel, and while that was a lucrative venture, the majority of her fortune came from alcohol and sly-grog bars in particular. These were establishments which operated after the legal closing time of 6pm, and in combination with the criminalization of cocaine in 1927, Leigh had the perfect pair of substances that she could sell at huge profits. At the height of her success, Kate became known as the “Queen of the Underworld”, and was believed to have as many as 20 of the sly-grog bars in operation at any given time. What was strange was that despite her making a fortune off of booze and drugs, she never drank or smoked her entire life.

Devine married James Edward (pictured) in 1917 and the pair moved to Sydney two years later.

Bitter lifelong rivals Kate Leigh (above, left) and brothel madam Tilly Devine (above right) made up in later years when the two crime queens were nearing the end of their careers.

Kate Leigh and Tilley Devine lived the majority of their lives in fierce competition with one another, yet at the end, their demises took on a rather coincidental decline.

However, it wasn’t their risky industry or their personal feud that brought these prominent crime figures down—it was money. They both had lots of it and they weren’t paying taxes. The Tax Department served Leigh a hefty fine for more than 10 years of unpaid taxes.

Leigh’s undoing really began in 1955 when the sly-grog trade was virtually killed off with the introduction of drinking till 10 pm. Leigh lived out the remainder of her life in a tiny room inside of her once illegal hotels and was financially independent on her nephew for the last few years of her life, which ended in 1964 at the age of 82. Devonshire St, Surry Hills is the terrace house where Kate dispensed sly grog and lived out her last years. She had a stroke there and fell down the stairs. She died five days later. Her funeral was held 200m along the street at St Peter’s Catholic Church with 700 people in attendance.

The truth of the matter is that the loopholes in the law that allowed the rise of these criminal empires, helped bring them down once those holes were firmly shut with new legislation. The Vagrancy Amendment Act of 1929 placed strict penalties on those who were caught in possession of razors without a valid reason, which in turn led to a major decline in the gang violence that had plagued the late 20’s. 1936 saw a new police commissioner brought into the area, and his efforts at curtailing the illegal movement of booze and cocaine went a long way to halting much of the trafficking. The biggest blow to the razor war was World War II which saw many of the street hoods drafted and sent off to fight, leaving the Sydney streets free of much of the criminal element who had helped keep the battle going.

At the height of Devine’s career, she had more than 30 brothels, a fleet of cars and properties around Sydney. Tilly divorced Big Jim in August 1943 after 25 years of marriage and years of abuse on the grounds of cruelty. Tilly married again on the 19th of May 1945 to ex-seaman and returned serviceman named Eric John Parsons, they were married happily for 13 years until Eric Parsons’s death in 1958.

Devine was fined £20,000 in 1955, her business took a hit but continued chugging along until 1968 when she sold her last brothel. She died in 1970 from chronic bronchitis that she had apparently been suffering with for 20 years in the Concord Repatriation General Hospital, Sydney on the 24th of November 1970. She was cremated with Catholic rites and few people attended her funeral.

Biography – Matilda Mary (Tilly) Devine – Australian Dictionary of …

Tilly Devine – Wikipedia

Tilly Devine & the Razor Gang Wars – State Records NSW

Love, Tilly Devine

Kate Leigh and Tilly Devine: The Queens of the Sydney Underworld

Sydney’s Jazz Age Criminal Queens Ruled the Streets With Razors …

Tilly Devine | 335 Malabar Road – The Sydney Morning Herald

Tilly DEVINE | The Australian War Memorial

Love, Tilly Devine – Broadsheet

heroinesofhistory – Tilly Devine

Tilly Devine and Kate Leigh – Razor Gang | Evil Ladies

Love Tilly Devine | Bars in Darlinghurst, Sydney – Time Out

The real Underbelly | Perth Now

Razorhurst – Tour Gangland Sydney – Tradesman’s Arms

Sydney’s Women in Crime: Tilly Devine & Kate Leigh – Xplore Sydney

Kate Leigh – Wikipedia

Photos emerge of Tilly Devine and Kate Leigh who controlled 1920s …

Kate Leigh and Tilly Devine: The Queens of the Sydney Underworld

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