NSW - Dark Stories True Crime Tours

1917: Tilly Devine Marries an Australian Soldier in London, Sealing a Turbulent Union

Matilda Twiss, born in Camberwell, London in 1900, married James Edward Devine, an Australian soldier serving in World War I, on 12 August 1917. Jim Devine, known as ‘Big Jim’, was a Victorian-born digger with a reputation for being sour and quick-tempered; Tilly was vivacious and already working as a prostitute. The pair were opposites in almost every way.

Tilly followed Jim to Sydney after the war, arriving in February 1920 and quickly building a criminal empire centred on Darlinghurst and Kings Cross. As the self-styled Queen of Woolloomooloo, she became one of the most notorious figures in the razor gang wars of the late 1920s and early 1930s. The marriage lasted 25 years before ending in divorce in 1943.

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Australia Darlinghurst Gang Kings Cross London Murder NSW Organised Crime Prostitution Scandal Sydney UK VIC Woolloomooloo

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1789: The Birth of Policing in New South Wales

On 8 August 1789, Governor Arthur Phillip authorised the formation of a nightwatch at Sydney Cove, drawing eight of the best-behaved convicts from the colony’s population. The Royal Marines, originally tasked with policing duties, had proved unwilling to discipline their fellow convicts, forcing Phillip’s hand. A free settler named John Smith had earlier been appointed as the colony’s first constable, becoming the first recorded police officer in Australia.

The Night Watch was joined by a Row Boat Guard, also composed of selected convicts. The Night Watch was replaced by the Sydney Foot Police in 1790 and evolved into an organised force that endured until the amalgamation of all New South Wales colonial police forces in 1862.

NSW Police Force recruits training with horses revolvers drill and gear

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Australia Colonial History NSW Police Prison Sydney

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1796: First Fleet Convict John Finlow Hanged in Sydney for Murder

John Fendlow (c.1768-1796), a tinsmith convicted at the Old Bailey in 1783 for highway robbery, arrived in Sydney with the First Fleet in January 1788. After time on Norfolk Island, he received a 30-acre land grant at Mulgrave Place in November 1794 and worked as a settler in the Hawkesbury region with his partner Eleanor Byrnes.

On 4 July 1796, Fendlow shot dead his servant David Lane after Lane attempted to assault Byrnes. Byrnes testified that all three had been drinking on a boat that evening, and that Lane had come after her in the house. Fendlow was hanged in Sydney on 8 August 1796.

HMS Mercury after 1809. By William Huggins. National Maritime Museum, Greenwich, London

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Australia Convict History Execution Hawkesbury Murder NSW Sydney

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1944: The Cowra Breakout: Bloodiest Mass Prison Escape of World War II

In the early hours of 5 August 1944, more than 1,000 Japanese prisoners of war held at the 12th Australian Prisoner of War and Internees Camp near Cowra, New South Wales, launched a mass breakout. Climbing over dead bodies and barbed wire, the escapees stormed the perimeter in what many had accepted as a suicide mission, a final bid to reclaim lost honour in the face of capture. It remains the largest mass escape of World War II and one of the bloodiest in history.

By the time the chaos subsided, 234 Japanese prisoners were dead and 108 wounded. Three Australian guards were killed, and a fourth officer was stabbed to death during the subsequent manhunt. Over 300 men were recaptured across the following nine days. The Cowra camp, opened in 1941, had grown to hold some 4,000 POWs and internees by 1944, including Italians, Formosans, Koreans, and Japanese non-commissioned officers, all held under Australia’s National Security Act 1939.

Police and troops search for Cowra POW camp escapees August 1944

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Australia Cowra Escape Massacre Military NSW Prison War Crime

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