Frederick James Siddartha Affleck: gay gentleman thief

Frederick James Siddartha Affleck fred affleck

In 1927, Frederick James Siddartha Affleck — Fred — the handsome gay son of an impoverished Queensland baronet, hit the big time in Sydney, robbing the houses of wealthy bachelors.

Fred Affleck

Frederick James Siddartha Affleck bitterly resented both his poverty-stricken childhood and that his father inherited a worthless title. Australia’s only other baronet, Sir Rupert Clarke, was also one of the country’s richest men. But Fred’s father could barely afford a pot to piss in. It seemed unnatural to have a title but no money. Fred would fix that. In 1925, he ventured forth in search of a dishonest living. The 20-year-old decamped to Sydney and forged a career in breaking and entering.

Fred Affleck suffered little consequence for his early crimes. He was still learning his trade, and pilfering usually only incurred fines. With prisons already congested, the authorities preferred to save space for truly dreadful offenders: murderers, rapists, debt defaulters, prostitutes, homosexuals and people who used indecent language in public places. Additionally, young offenders often benefitted from judicial leniency, so Fred lowered his age by a year, giving his birthdate as 1906.

In 1927, the petty crim hit the big time. He, Reg Worters and Albert Gibbs devised a scheme whereby they gained access to some of Sydney’s swankiest homes by posing as gardeners and flower sellers.

Prince del Drago

They robbed wealthy businessmen, civic dignitaries, celebrated sports stars and even nobleman Prince Alfonso del Drago. The wealthy Italian bachelor moved to Sydney in 1924 and, for some unknown reason, never returned home. Papers described him as Sydney’s most immaculate dresser. He was a trusted social escort for visiting Italian noblewomen and Sydney’s Catholic society matrons. During the 1920s, he often promenaded through Potts Point several times a day, returning home only to change into a fresh suit before each outing. Fred Affleck was not the only young man to ever face court charged with robbing the prince.

Lady Affleck was no doubt proud to learn Fred visited del Drago’s apartment. She always said that Frederick James Siddartha Affleck would one day take his rightful place among the noble houses of Europe. Now here he was, in one of their homes. Admittedly, not by invitation, and more balaclava than black tie and tiara, but Fred Affleck was there.

And they said he’d never make it!

fred affleck
Rich, titled, immaculate dresser, friend of Mussolini and a looker.

Slim, dark-haired flower seller

Sadly for Fred, the police eventually pinpointed something in common to all the ransacked mansions – him! He had either worked as a casual gardener, delivered flowers or performed some other unspecified service for the occupants of each of the burgled residences.

As a newspaper reported, “Detectives came to the conclusion that the slim, dark-haired flower-seller was merely using the offerings of the garden beautiful to spy out likely cribs to crack.”

Following a two-year stint in Long Bay Gaol, Fred was back at it. Combining his previous experience with lessons learned from old lags in Long Bay, he targeted less distinguished victims. He hit the middle class instead of the swells whose names littered newspaper social columns. Less high-profile victims would not exert as much pressure on police investigators.

fred affleck Frederick James Siddartha Affleck
Fred Affleck, Long Bay Gaol. December 21, 1927.

Fred also avoided the company of career criminals. The coppers kept a constant eye on the likes of former accomplices, Worters and Gibbs. Fred Affleck instead took on an apprentice with no prior convictions. He and 18-year-old Harry Hooker roared through dark streets on a stolen motorbike, raiding homes within a three-mile radius of their Mays Hill base — Parramatta, Harris Park, Granville and Westmead. The pair robbed scores of houses; a newspaper reported the police estimated the total value of their ill-gotten gains at between £3000 and £4000 ($250,000 – $340,000 today).

Long Bay Gaol

The sudden crime wave unsettled the district. Although the infamous Razor Gangs continued to terrorise inner-city suburbs, people further out generally felt safe. Until they began to read persistent reports of burglars plundering homes as residents slept or stripping houses bare of valuables in the absence of the occupants.

The thieves’ brazen indifference to the risk of capture made them appear unstoppable. After ransacking a doctor’s residence, they hung around to quench their thirst on the medico’s sparkling hock, wearing gloves to avoid leaving fingerprints on the glasses. The cheeky bastards purloined Dr Kearney’s champagne for a future celebration. But at another house, they found only very plain fare — crackers and cheese — and a total lack of intoxicating liquors. Accustomed by now to the finer things in life, a disappointed Fred jotted down a smart-arse note to the miserly householder.

“The people in this house must be Scotch.”

The spate of robberies ended when a mate snitched on Fred. Police apprehended Harry soon after despite Fred’s refusal to dob. Local residents slept easier. The recovery of a Colt automatic pistol and set of handcuffs stolen from a policeman’s home was especially welcome.

Magistrate Flynn expressed the gratitude of a relieved community.

“I congratulate the police of Parramatta on clearing up this great number of burglaries. It is very satisfactory.”

Meanwhile, the police and newspapers hailed Fred as a criminal mastermind, ‘a modern counterpart of the fictional Raffles’.

A modern Raffles

The crime stories of E W Hornung chronicled the misdeeds of English gentleman thief A J Raffles and male offsider Bunny Manders. During the Great Depression, Raffles surpassed even the fictional detective Sherlock Holmes in popularity. The charismatic reprobate’s cynicism and moral ambivalence contrasted with his sidekick’s overwrought emotionalism. Hornung modelled the criminal duo on friends. Oscar Wilde provided the template for Raffles while Bunny borrowed heavily from Lord Alfred Douglas — aka Bosie — Wilde’s erratic sometimes lover.

An 1898 book illustration of Raffles (right) and Bunny.

And therein lay the coded backhand in the applause for Fred’s criminal genius. In an era when laws, social taboos and contingencies of good taste limited what newspapers could publish, the public knew to read between the lines. Oscar Wilde was a byword for buggery, and anyone wishing to infer homosexuality simply mentioned the Irish playwright. Likewise, mention of the gentleman thief linked Fred and Harry to the questionable intimacy of Raffles and Bunny. And the cops probably enjoyed a giggle over the ‘novel twist’ employed in the most recent Raffles movie. Hornung’s creation became a woman in Colombia Pictures’ Lady Raffles.

It was all just a little bit queer.

The police telegraphed to the public that Fred was not a real man. He was an Oscar Wilde. A burgling bugger, and according to young Harry Hooker’s lawyer, a corrupter of innocent youth. Mr Murray denounced the (marginally) older man for leading his gullible client astray. Harry escaped with good behaviour while Fred returned to Long Bay Gaol for a further two-year stint.

One cardinal rule

Despite the value of his heists, Frederick James Siddartha Affleck failed at his chosen vocation.

Villainy has one cardinal rule — don’t get caught. Fred always got caught.

He was caught over and over again. So much so, the NSW courts eventually branded him a habitual criminal. He also never knew when to zip it. Catching Fred saved the cops substantial legwork. The moment they had him, he blabbed.

As he did in Brisbane in 1937 when local cops caught him, his brother and a mate running a gay brothel out of an inner-city studio apartment.

But that’s a story for another day.

Related reads:

Prison Sex: Fred Affleck and others.

Prison Sex Long Bay Frederick James Siddartha Affleck
Fred Affleck, Albert Gibbs and Reg Worters

Consensual buggery in colonial Australia.

Consensual Buggery in Colonial Australia

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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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