The reputations of some of Sydney’s most prestigious private schools are being tarnished by pampered alumni finding themselves on the wrong side of the law.
The same golden boys and girls who once celebrated top marks and elite university offers with Dom Pérignon are now showing up in courtrooms a decade later, trading champagne for drug tests and defence lawyers.
Their crimes are various – from cocaine possession to fraud – but the circus is always the same.
As a society gossip columnist and regular at Waverley Local, I’ve witnessed this posh trainwreck unfold in real time, as rich kids with Old Boy ties file in, heads bowed, accompanied by expensive defence lawyers hired by Daddy.
Let’s begin with one of the more serious sinners. Enter Jake Prindiville: First XV rugby star, now first in line for jail lunch.
Once a promising athlete at the $40,000-a-year Scots College in Bellevue Hill, Jake has gone from sideline huddles to a court-ordered lockdown after he was caught in a plot to shift 12kg of cocaine. Yes, 12 kilos – hardly personal use.
The judge called it ‘spontaneous’. His lawyer blamed money troubles. Either way, he pleaded guilty and went from holidays in South East Asia to a two-year stretch in Silverwater before any possibility of parole.
Jake’s mate Hugo Ball, a fellow Scots alum, is a one-man high-society horror show.
Hugo, also 28, ticked all the boxes of an eastern suburbs prince – Bellevue Hill mansion, private school pedigree and enough scandal to fuel a Netflix mini-series.
After a drug-fuelled argument, his mother – yes, his mother – stabbed him with a butcher’s knife. The incident nearly killed him, resulted in a conviction for reckless wounding – though she avoided jail – and landed both of them in the headlines.
Since then, Hugo has been in heaps of trouble. In June, he pleaded guilty to charges including larceny, entering enclosed land without lawful excuse, drug possession and behaving in an offensive manner in public.
The charges relate in part to an incident in April when – per agreed facts – the troubled young man sneaked into an Anytime Fitness gym in Potts Point and was caught on CCTV rifling through lockers and taking various items of property.
These days, he’s peddling silver bullion on Facebook.
Meanwhile, across the lawn at glittering Cranbrook – known for educating the likes of James Packer, Nick Cave and Mike Cannon-Brookes – various other alumni are doing their best to tarnish the school’s reputation as it prepares to go co-ed.
Sydney start‑up millionaire Andrew Spira, the founder of Pineapple Funding and nephew of ABC Chair Ita Buttrose, once had it all.
But behind the sleek business card, his life was unravelling.
In mid‑2023, the 26-year-old spiralled into a drug‑induced psychosis so severe that he was arrested in Darwin while attempting to flee the country using a fake passport – despite having permission to leave under bail conditions set in New South Wales for a domestic violence charge.
‘[Mr Spira was] probably one of the first people to use a fake passport to get out of , whilst holding their real passport with no restraints on that passport,’ his lawyer Nicholas Goodfellow told the court.
That’s embarrassing!
Spira pleaded guilty to a raft of charges and was slapped with a $39,000 fine plus an 18‑month good‑behaviour bond.
When fellow Cranbrookian and Bondi real estate agent James Masselos was busted with a baggie of coke and an MDMA cap and hauled before Magistrate Jacqueline Milledge, we knew he was in for a dressing-down.
Noting his remorse and his cooperation with police, Milledge bluntly told him: ‘You probably thought you were bulletproof.
‘The fact that you are exposing yourself to criminal activity [with a] real likelihood there could be a conviction… why didn’t you think of that?’
It’s a good question. Masselos received an 18-month conditional release order with no conviction recorded.
Warren Ginsberg is another property bro with a nose for trouble.
The alumnus of Emanuel School – a Jewish institution with a heritage-listed campus in ritzy Randwick – was caught in possession of cocaine during a Bondi police crackdown in August 2021, shocking precisely no one.
Warren’s defence team insisted this wasn’t addiction – just good, old-fashioned heartbreak. He was convicted and fined $500 by Magistrate Carolyn Huntsman, but his bench-pressing lawyer Bryan Wrench later indicated he wished to appeal.
While the outcome of that appeal bid is unclear, the fact it was Ginsberg’s third drug possession charge since 2007 – he was just 19 when he first landed in trouble – certainly wasn’t a good look for the Ray White Double Bay director.
Turning to more serious matters, meet heiress-turned-inmate Harriet Wran.
An Ascham old girl and the daughter of former NSW Premier Neville Wran, Harriet had the political pedigree and society connections to make big things happen… and she did, when she got involved in a robbery that ended in murder.
She served time for acting as an accessory after the fact, but just a few years later was back in court when police found meth and stolen goods in her car.
Now living quietly with her horses at her mother’s country estate, Harriet is still a long way from society luncheons and designer-filled closets.
Gucci in one hand, stolen goods in the other… meet Amanda Arbib.
Once a polished private school girl from Sydney’s east, Arbib seemed destined for success – until tragedy, addiction and legal woes derailed her.
The once-promising Moriah College alum took a criminal detour into ice addiction and mail theft, stuffing stolen goods into a designer handbag and padding her bra with drugs.
She showed up to court in 10-inch heels looking like a mob wife, and avoided jail thanks to her rehab efforts and commitment to sobriety.
Across the bridge, Annabelle ‘Annie’ Miller, who attended Queenwood School for Girls in Mosman, knows a thing or two about theft.
Annie, 26, was hired to care for a North Shore widow’s children. Instead, she helped herself to more than $12,000 using the grieving mother’s credit card, purchasing puppy pads, concert tickets, spa days and Camilla kaftans.
Naturally, the stolen designer goods ended up on Facebook Marketplace, because what’s petty crime without a digital footprint?
She was convicted of one count of dishonestly obtaining financial benefit by deception after pleading guilty.
Miller was handed a 12-month community correction order and required to complete 50 hours of community service. She was fined just $1,000, although she must also pay back the $12,315.90 to the widow.
She now lives in a Mona Vale granny flat.
Then there’s Paris Ow-Yang, the teen rebel who went from OnlyFans to only fines.
A Frensham graduate with a $50k Mercedes, Paris got behind the wheel while four times over the legal limit and crashed in Point Piper.
After being banned from driving, she later returned to court for stalking, assault and property damage following a domestic meltdown.
And finally, how could I forget the Frensham fraudster: Annabel Walker.
In a textbook case of champagne tastes on a Ponzi scheme budget, Walker scammed friends, boyfriends and bosses, leaving her victims more than $30,000 out of pocket.
The Bowral socialite was sentenced to 10 months behind bars for fraud.
Finally, two honourable mentions: Coco Potgieter and Elisha Dalah.
Coco, a former Frensham house captain and the daughter of well-known Sydney artist Johann Potgieter, crashed her car in Point Piper and failed a breath test, then got slapped with a driving ban and an $800 fine.
Elisha – whose brother Nathan is the founder of Fishbowl – found herself tangled in a drug-fuelled mess involving none other than fallen TV star Andrew O’Keefe.
After a suspected heroin overdose, she saved the former Deal or No Deal presenter’s life – then admitted to buying the drugs.
So what’s going on with Sydney’s gilded youth? Maybe it’s a case of too much money and not enough consequences.
Either way, it seems the private school halo hasn’t just slipped… it’s rolled down Bellevue Hill and straight into the back of a paddy wagon.