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Image credit: Watercolour of Cockatoo Island [Collection of views, ca. 1840-1848 by J.S. Prout], Dixson Galleries, State Library of New South Wales (out of copyright)

Cockatoo Island's First Nations convicts

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5 min read
The stories of First Nations convicts are part of the historical narrative of Cockatoo Island's penal establishment (1839 to 1969). One of the First Nations convicts sent to the island was Toby.

[Disclaimer: Aboriginal and Torres Strait Islander Peoples are advised that this story may include culturally sensitive material. Reader discretion is advised.]

Toby was a Wonnarua man and one of a dozen Aboriginal people who died in custody during the first few years of Cockatoo Island’s convict penal establishment. Volunteer researcher, Michele Harper canvasses the life of the man who was born ‘Booral’ and spent his twenties actively resisting European settlement.

Born in 1811, Toby hailed from the Wonnarua nation in the Hunter Valley region of NSW. Although little is known about his early life, his people were dispossessed of their land as timber cutters, squatters and convicts began to settle in the Newcastle region. According to historical records, Wonnarua people disliked convicts and regularly captured and returned runaway. It is believed this resentment stemmed from the poor treatment of Wonnarua women at the hands of the interlopers.

Toby spent time working as a labourer before joining a group of Aboriginal men, in 1834, to carry out raid on farms around Brisbane Waters on the Central Coast. The raids were retaliation for being fired upon by European settlers and would have involved the burning of crops and killing of cattle. During this period, Toby was arrested and convicted of robbery and putting a farmer in fear of his life. Although he was originally sentenced to death, his sentence was commuted to incarceration at Goat Island on Sydney Harbour.

In 1839, Toby was again arrested, this time for assaulting a farmer at Maitland. The farmer had been walking home when a group of men struck him with spears and stole his jacket. Toby and another Wonnarua man, Murphy, were apprehended at the Green Hills camp, three miles from Maitland, and both were sentenced to ten years’ imprisonment on Van Diemen’s Land. Toby’s sentence was shortened to three years, however, and he was instead sent to Cockatoo Island, leaving behind a wife and young son.

When Toby arrived at Cockatoo Island in February 1840, he was clamped in leg irons (the island’s Aboriginal prisoners usually wore leg irons for the duration of their incarceration) and slept separately from the rest of the convicts in a building next to the hospital. He was, however, joined by Murphy, whose sentence had also been commuted to Cockatoo Island.

Toby was soon tasked with cutting stone, which he was said to be adept at, having undertaken this work at Goat Island. Toby died, at the age of 30, on 31 December 1841, during a wave of sickness on the island. The inquest – conducted at the Three Tuns Tavern on the corner of Elizabeth and King Streets – determined he had died from inflammation of the lungs and dysentery; however, a verdict of death from natural causes was recorded. A newspaper report noted than Toby had been suffering for some time but had refused medicine.

Toby was one of a dozen Aboriginal prisoners who died in custody during the first few years of the convict penal establishment on Cockatoo island. His fellow countryman, Murphy, was the only Aboriginal prisoner to depart the island a free man, after serving out his time.


  • Castrique, Sue, (2014) Under the Colony’s Eye. Gentlemen and convict on Cockatoo Island 1839-1869. Anchor Books Australia
  • The Sydney Morning Herald, Monday 3 January 1842, page 3
  • The Sydney Free Press, Tuesday 4 January 1842, page 2.

Article was originally published on 23 July 2020.


Toby was sentenced to ten years’ imprisonment on Van Diemen’s Land. His sentence was shortened, however, and he was instead sent to Cockatoo Island.

– Michele Harper

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