Matilda Mary Devine, better known as Tilly Devine, was far from the traditional Australian matron one might picture from her name. Instead, she was a figure associated with the underbelly of Sydney's crime world during the interwar years, her activities spanning an array of illicit pursuits including sly-grog, razor gangs, and, most notably, prostitution. In her heyday, Devine was more than just another criminal; she was a notorious figure whose influence spread throughout the city, making her a prominent folk figure in Sydney's crime history.

Born in 1900 in London, England, Devine's early life was marked by hardship and poverty. It was these difficult circumstances that perhaps set the stage for her eventual descent into the criminal world. She left school at a young age to work in a factory, but soon found herself drawn into the world of prostitution. By the age of 16, she was working as a sex worker in London's seedy underbelly.

In 1917, Devine married an Australian serviceman named James Devine. The couple migrated to Australia in 1919, settling in Sydney. It was here that Tilly Devine began to carve out an empire that would make her one of the city's most notorious crime bosses.

Upon their arrival in Sydney, Devine set up a string of brothels in the city's red-light district. This was a time when prostitution was illegal in New South Wales, but Devine found a loophole in the law, which did not specifically prohibit running a brothel. She quickly became Sydney's most infamous madam, amassing wealth and power in the process.

Devine's operation was not without its challenges. She faced opposition from rival crime figures, including the infamous Kate Leigh, with whom she engaged in a bloody turf war. This feud, which played out in the streets of Sydney, was marked by violent clashes between razor gangs aligned with each woman. The razor became the weapon of choice because a law in 1927 had made it illegal to carry a gun without a permit. The razor gangs, so-called because they used cutthroat razors as weapons, became notorious for their brutal violence.

The law enforcement of the time was often corrupt, and Devine was frequently able to bribe police officers to turn a blind eye to her operations. However, she was not always able to evade justice. She was arrested multiple times on various charges, including assault, offensive behaviour, and indecent language. In 1925, she was convicted of procuring a miscarriage for one of her sex workers and was sentenced to two years in prison.

Devine's criminal activities extended beyond prostitution. She was known to operate sly-grog shops, illegal establishments that sold alcohol during the Prohibition era. She was also involved in drug trafficking, with police suspecting her of being behind a large portion of the cocaine that circulated in Sydney during the 1920s and 1930s.

The public reaction to Devine was mixed. While many viewed her with disgust and revulsion, others saw her as a Robin Hood-like figure. She was known to be generous with her wealth, often donating to charitable causes. Her lavish lifestyle, which included a luxurious home in the prestigious suburb of Maroubra and a love for ostentatious jewellery, was a source of fascination for the public.

Devine's story was widely covered by the media, with her exploits regularly making headlines. She became a tabloid sensation, with newspapers often highlighting her flamboyant lifestyle and criminal activities. Her feud with Kate Leigh was particularly sensationalized, with the media often painting the two women as archenemies locked in a deadly battle for control of Sydney's underworld.

Devine's reign as Sydney's crime queen came to an end in the 1940s. By this time, her wealth had dwindled, and she was facing increasing pressure from law enforcement. In 1945, she was charged with tax evasion, which led to a significant financial hit. Her husband, James, died in 1953, leaving her alone and with diminished influence in the criminal world.

In her later years, Devine lived a relatively quiet life. She passed away in 1970 at the age of 70. Her death marked the end of an era, but her legacy as one of Australia's most notorious crime figures endures.

The story of Tilly Devine has had a significant cultural impact in Australia. Her life has been the subject of numerous books and films, including the popular television series "Underbelly: Razor," which dramatizes the razor gang wars of the 1920s and 1930s. Her life story serves as a stark reminder of a darker side of Sydney's history, a time when the city was ruled by ruthless crime bosses.

While Devine's life was undoubtedly marked by violence and criminality, it also serves as a testament to the power of resilience and determination. Despite the odds stacked against her, Devine managed to rise from the depths of poverty to become one of the most powerful figures in Sydney's criminal underworld. Her story, while far from commendable, is undeniably fascinating, offering a unique glimpse into the city's checkered past.