Did Jack the Ripper Live in Darlinghurst?

Frederick Deeming once lived quietly on Riley Street, Darlinghurst, before becoming one of the 19th century’s most infamous killers, and a possible Jack the Ripper suspect.

By Elliot Lindsay

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In the early 1880s, along Riley Street in Darlinghurst, Frederick Deeming lived a quiet domestic life. He was a plumber by trade, moving between addresses at 162 and 165 Riley Street, and for a time, he appeared entirely settled. His wife and children lived with him there, and the household seemed ordinary enough to pass without remark. One of his children was even born in that house at 162 Riley Street in 1886. He spoke often of his family, referring to them affectionately, and to neighbours and employers alike, he presented himself as a respectable, if somewhat boastful, working man.

There were, of course, small inconsistencies. He talked too much of wealth, of travel, of opportunities that never quite materialised. He possessed jewellery that did not match his means, displaying diamonds with a curious pride. But Sydney in those years was full of men constructing new identities, and Deeming did not stand out enough to warrant suspicion. He worked, he lived among others, and he raised his children in the crowded inner suburbs of the city.

And yet, even then, there were signs of another life running alongside the first.

In the evenings of 1885 and 1886, Deeming would leave Riley Street behind and ride east toward Woollahra. There, at Ackland’s Hotel on Queen Street — today the Woollahra Hotel — he began an affair with a 21-year-old barmaid named Annie Spain. It followed a familiar pattern. He courted her with confidence, spoke of money and travel, and promised marriage. To Annie, he was a man on the verge of fortune, temporarily anchored in Sydney but destined for greater things. She had no reason to suspect that only a few miles away, in Darlinghurst, he was living as a husband and father.

The deception did not last. Annie discovered the truth before any marriage could take place, and when she confronted him, the affair ended abruptly and bitterly. She threw a whisky glass at his head when he entered the bar; he ducked, and it smashed against the wall. The shock of the revelation — so the newspapers later claimed — affected her deeply. Within a few months, in April 1886, she was dead, and though no formal charge could be laid at Deeming’s feet, his conduct was widely blamed for her decline. In retrospect, it stands as a grim early glimpse of the harm he could inflict on those who trusted him.

At this point, Frederick Deeming might still have been dismissed as a liar, a womaniser, and a petty criminal. There was little to suggest that he was anything more. However, this man would soon become a household name around the world due to a level of cruelty and evil that was unfathomable to most people.

Who was Frederick Bailey Deeming?

The answer would not come from Darlinghurst, but from Melbourne.

In March 1892, in a small cottage at Windsor, a prospective tenant complained of a foul odour. Investigations led to the lifting of a hearthstone in the fireplace, and beneath it, in a shallow cavity filled with cement, was found the body of a woman. Her skull had been crushed, her throat cut, and her body forced into a confined space under the floor. It was a crime of shocking brutality, but also one that suggested careful planning. The house had been rented under an assumed name. Cement had been purchased under the pretext of repairs. Everything pointed to a deliberate and methodical act.

The man who had occupied the house had vanished. But not without leaving traces.

Witnesses recalled a well-dressed man, fond of jewellery, who had arrived with a woman and then disappeared shortly after Christmas. Laundry records, shipping manifests, and chance encounters began to build a picture. The name he had used was “Williams.” From there, the investigation spread outward, linking fragments of information across cities and continents.

In Sydney, detectives recognised the description almost immediately. “Williams,” they realised, was Frederick Deeming — the quiet plumber from Riley Street.

As the investigation deepened, the full extent of his crimes began to emerge. In England, at a place called Rainhill, police searched a house he had previously occupied. There, beneath the floor, they made a discovery that surpassed even the horror of Windsor. The bodies of a woman and four children had been buried in the same manner — encased in cement, concealed beneath the house. They had been murdered with similar brutality.

It was then that the story of Riley Street took on a far darker meaning.

Those children buried in Rainhill were not strangers.

They were his children.

The same children who had lived with him in Darlinghurst. The same children who had played in the narrow streets off Riley Street, who had been part of an ordinary Sydney household, and whose lives had once seemed as unremarkable as their father’s.

And yet, years later, their father had abandoned them and their mother to start a new life in England, marrying another woman in an act of bigamy. When the young, destitute family finally tracked him down and discovered his new life, Deeming cruelly murdered them all including his youngest who was 18 months old.

The realisation transformed the entire narrative. The family life on Riley Street was not a stable foundation, but a stage in a longer, more sinister pattern. Deeming did not simply deceive women or abandon relationships; he erased them. When his family became an obstacle—when they stood in the way of new identities and new marriages—he eliminated them with chilling efficiency.

The pattern repeated itself.

In Melbourne, the victim at Windsor — Emily Mather, a native of Rainhill, England — had been courted, married, and murdered within a matter of weeks. Even after burying her beneath the hearthstone, Deeming moved on, travelling openly and beginning yet another courtship. On a voyage to Sydney, he met a young woman and proposed marriage, presenting himself once again as a man of wealth and opportunity. Only the discovery of the Windsor body prevented her from becoming his next victim.

Deeming was eventually tracked across Australia, identified through witness testimony and correspondence, and arrested in Western Australia. His trial in Melbourne drew immense public attention. The evidence against him was overwhelming, linking him not only to the Windsor murder but also to the Rainhill killings in England. Attempts were made to argue that he was insane, that he suffered from fits or hereditary mental illness, but these claims failed to sway the court. He was convicted and sentenced to death.

At Melbourne Gaol, he was hanged in May 1892, bringing a formal end to his life and crimes.

But even as the case seemed to close, a new and extraordinary idea began to circulate.

Some suggested that Frederick Deeming was not merely a murderer, but the murderer — the figure who had terrorised London just a few years earlier. The crimes in Whitechapel, attributed to the unknown killer known as Jack the Ripper, bore certain similarities: brutality, cunning, and the ability to evade capture. Deeming’s movements across continents, his use of aliases, and his apparent lack of remorse made the theory seem, to some, plausible.

The suggestion that he might be connected to the Whitechapel murders captured the imagination of the public. Newspapers speculated, lawyers hinted, and the idea took on a life of its own. Others dismissed it, pointing to inconsistencies in dates and locations. Even at the time, the theory was controversial and widely debated.

And yet, it refused to disappear entirely.

Because if it were true — or even possible — then the implications are extraordinary. It would mean that one of the most infamous killers in history had not only passed through Sydney but had lived quietly in its inner suburbs. That the man who raised a family on Riley Street and who courted a barmaid in the Woollahra Hotel, was Jack the Ripper!

There is no definitive answer. History often leaves us with fragments and possibilities rather than certainty. Yet the story of Frederick Deeming — traced from Darlinghurst to Rainhill and Windsor — raises a deeply unsettling question. Was Deeming in any way responsible for the barmaid, Annie Spain’s death? 

The evidence is limited: she died at just 21 years of age, her funeral was held on 19 April 1886, just three months after she discovered the truth about Deeming. Nothing more is recorded that would conclusively link him to her death. Yet, in light of what is now known about his capacity for violence, the possibility is difficult to ignore. How could a young woman die of a “broken heart” as witnesses have suggested? The timing is striking, particularly as it coincides with the birth of one of Deeming’s children. Did he kill her to keep her quiet?

We may never know the truth. But for a time, at least, a man capable of extraordinary brutality lived an apparently ordinary life on Riley Street, Darlinghurst, drank in the local hotels and walked the local streets with the family he would eventually murder. Another strange chapter in the history of Darlinghurst.