Prison - Dark Stories True Crime Tours

1809: Thomas Dowlan Hanged in Sydney for Burglary at Hawkesbury

Thomas Doolan, described as an old offender who had been tried several times in the colony, was convicted of forcibly breaking into the house of John Styles at Hawkesbury. He had previously saved himself from execution by turning informant against his accomplices, some of whom were hanged on his testimony.

Doolan was hanged in Sydney on 26 August 1809. Court records from the same period reveal he had also been among those who burglariously broke into the dwelling of a settler named Thomas Harley, beating the occupants and ransacking the house, though he did not live to face that additional charge.

Motorway 1 bridge over Hawkesbury River near Sydney with traffic

⬅ See all events from 26 August

Australia Burglary Execution Hawkesbury NSW Prison Robbery Sydney

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1909: Long Bay Gaol Opens on the Shores of Botany Bay

Sydney's Long Bay Gaol opened in 1909 on the shores of Botany Bay, and over the following century it would become one of the most storied prisons in the country. Its walls held razor gang queens Tilly Devine and Kate Leigh, escape artist Darcy Dugan, and gangsters Chow Hayes and Neddy Smith.

Long Bay also housed some of the darkest figures in modern Australian criminal history, including corrupt former detective Roger Rogerson and serial killer Ivan Milat, who died there in 2019. Russell 'Mad Dog' Cox staged a daring breakout from the prison's maximum-security unit, cementing the gaol's reputation as a place where Australia's most dangerous and notorious converged.

Historic prison buildings at Long Bay Gaol in Australia

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Australia Corruption Escape Gang Murder NSW Organised Crime Prison Serial Killer Sydney

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1972: The Brooklyn Bank Siege That Inspired Dog Day Afternoon

On August 22, 1972, John Wojtowicz and Salvatore Naturile attempted to rob a branch of Chase Manhattan Bank at 450 Avenue P in Gravesend, Brooklyn. A third accomplice fled before the robbery began after spotting a police car. Rather than escaping with the cash, Wojtowicz and Naturile held seven bank employees hostage for fourteen hours. Wojtowicz, a former bank teller, had working knowledge of bank operations, but the plan unravelled completely.

Naturile was shot and killed by an FBI agent during the final moments of the standoff. Wojtowicz was arrested and sentenced to 20 years at Lewisburg Federal Penitentiary, serving five. The story became the basis for the 1975 film Dog Day Afternoon, starring Al Pacino.

ID 164823257 © Photovs | Dreamstime.com

⬅ See all events from 22 August

Kidnapping Organised Crime Prison Robbery USA

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1865: John Wesley Hardin Gunned Down in an El Paso Saloon

John Wesley Hardin was one of the most feared gunfighters of the American Old West. Born in Texas in 1853 to a Methodist preacher, he killed his first man at 15 and spent the following decade evading lawmen across the South. Sentenced to 24 years for murder in 1877, Hardin claimed to have killed 42 men, though historians estimate the true figure exceeded 20. He studied law in prison and wrote a self-aggrandising autobiography, widely noted for its exaggerations.

Within a year of his 1894 release, Hardin was shot dead by constable John Selman in the Acme Saloon in El Paso. Hardin had been gambling, rolling dice at the bar, and his last words were reportedly “Four sixes to beat.” Moments later, Selman walked up behind him and shot him in the head. Hardin was 42 years old.

⬅ See all events from 19 August

Gang Murder Organised Crime Prison Trial USA

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