LGBT history: Australia’s earliest known gay love letter

gay love letter
Image: Norfolk Island Jail y Steve Daggar

Most of what we know of LGBT Australians in the colonial era comes from court and prison records. Australia’s earliest known gay love letter is no different. Indeed, it is the letter of a convict to the person he loved most — a man he knew he would never see again.

Denis Prendergast (or Pendergast) arrived in Australia as a convict in 1838. He disembarked in Van Diemen’s Land but sometime later ended up on Norfolk Island. That exquisitely beautiful but notorious island housed the men colonial administrators judged ‘the worst description of convicts’. Norfolk Island gained a reputation as the cruelest of all Australian penal colonies.

In 1846, a new administrator took away one of the few ‘luxuries’ the inmates enjoyed — personal billies and kettles used to cook their meals. Determined to crack down on even the smallest liberties allowed to the convicts by the previous administrator, the petty tyrant decreed that in future all meals would be cooked in bulk.

Some convicts decided they’d had enough.

William Westwood

Nearly a decade before, William Westwood received a sentence of transportation to New South Wales for stealing a coat. Assigned as a servant on a station, he attempted to escape because of mistreatment by an overseer. For that, he received 50 lashes. William planned his next escape better!

Known as the ‘gentleman bushranger’ for his courtesy and refusal to hurt anyone, William went by the bushranging alias of Jackey Jackey.

Captured a number of times, he received 50 to 100 lashes with every new term of imprisonment. But that never dissuaded him from escape. Once, he and two other prisoners absconded from Port Arthur. Located on a peninsula, only a 30-metre-wide isthmus connected the prison to the mainland. Soldiers and half-starved dogs guarded the passage. William and two other convicts decided to swim to the mainland. Only William made it. The other two fell victim to shark attack.

Eventually, the gentleman bushranger found himself sentenced to Norfolk Island.

But by 1846, he wearied of the life of rigid discipline and harsh punishment. The confiscation of the cooking pots proved the last straw. He addressed his fellow prisoners.

“I’ve made up my mind to bear this oppression no longer. But, remember, I’m going to the gallows. If any man funks, let him stand out. Those who want to follow me — come on!”

1,600 convicts joined William in the riot. An overseer and three constables were killed. However, when confronted by a line of soldiers with muskets at the ready, the convicts surrendered.

William and eleven other prominent leaders of the rebellion were sentenced to hang. Among them, Denis Prendergast. After the mass execution, the men’s bodies were dumped in a pit outside the cemetery.

Norfolk Island’s reputation

Other than beauty and cruelty, Norfolk Island bore a reputation for one other thing…

‘Crimes’ that the Catholic Vicar-General of the colonies told an inquiry “would make your blood to freeze and your hair to rise erect in horror.”

300 convicts in same-sex ‘marriages’

The Vicar-General claimed up to two-thirds of the island population indulged in same-sex ‘crimes’. In the year of the Cooking Pot Riot, a visiting magistrate reported that as many as 300 of the convicts on the island lived together as ‘man and wife’.

We don’t know if homosexuality played any role in the Cooking Pot Riot. But we do know at least one of the ring-leaders was gay.

Because on the eve of his execution, Denis Prendergast penned a letter that survived to become Australia’s earliest known gay love letter.

I hope you won’t forget me when I am far away and all my bones is moldered away. I have not closed an eye since I lost sight of you. Your precious sight was always a welcome and loving charming spectacle.

Dear Jack,

I value Death nothing but it is in leaving you my dear behind and no one to look after you…

The only thing that grieves me love is when I think of the pleasant nights we have had together.

I hope you won’t fall in love with no other man when I am dead and I remain your True and loving affectionate Lover.

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Destiny Rogers

Destiny Rogers embarked on her career in the media industry immediately after high school, initially joining Mirror News, which later evolved into News Ltd. She fondly recalls editing Ian Byford's 'Passing Glances: A History of Gay Cairns' as one of her most fulfilling projects. Additionally, Destiny co-researched and co-wrote 'The Queen's Ball', chronicling the history of the world's longest-running continuous queer event. Her investigative work on the history of Australia's COON Cheese and Edward Coon culminated in the publication 'COON: More Holes than Swiss Cheese', a collaborative effort with Dr. Stephen Hagan. Destiny's journey at QNews began as a feature writer, and she was subsequently elevated to the role of Managing Editor of QNews Magazine in 2018. However, in July 2022, she decided to resign from this role to refocus on research and feature writing. For contact, please reach out at

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