Geoffrey Edelsten continued to live the high life up until his final breath despite losing much of the fortune chasing younger and publicity for decades.
As creditors worked to tear apart his fallen empire, Edelsten maintained a fleet of sports cars and enviable real estate portfolio.
Daily Mail Australia can reveal Edelsten, who will be farewelled in Melbourne on Wednesday, held onto a king’s ransom of luxury goods even as the wolves circled his doors.
Brynne and groom Geoffrey Edelsten on their wedding day alongside Edelsten’s mum Esther Edelsten (far right)
Geoffrey Edelsten was found dead inside his apartment at Balencea Apartments on St Kilda Road on Friday
Edelsten drove his ex-wife Brynne to bankruptcy after a prolonged legal challenge
A series of disastrous financial decisions had left Edelsten a bankrupt in the United States, but it would take years for forensic financial experts to track down his missing millions.
In 2014, after busting up with his second wife Brynne, Edelsten was still believed to be spending up to $48,000 a month on women, flights and whatever else tickled his fancy.
The disgraced doctor, who was jailed in 1990 for perverting the course of justice and soliciting Christopher ‘Mr Rent-a-Kill’ Dale Flannery to assault a former patient, had sold his medical empire, Allied Medical Group, to Sonic Healthcare for a reported $125 million just years earlier.
Edelsten pocketed about $65 million from the sale, which he proceeded to squander through a series of calamitous deals.
He invested in a fashion label and a casino in the Dominican Republic and bought into distressed properties at the height of America’s post-subprime mortgage crisis.
At the same time he blew $4 million on a Bombadier Challenger jet while losing hundreds of thousands of dollars gambling in just one visit to the casino.
Daily Mail Australia revealed on Saturday Edelsten had offered his ex-wife Brynne a $50million ‘deal’ to marry him just two weeks after they met in Las Vegas in 2008.
‘I’ll provide you with a brand new motor vehicle more befitting a classy lady like you. An upmarket brand, perhaps a convertible. It will make your friends green with envy,’ he wrote in an email proposal.
‘I’ll pay you twice as much as you earn now and increase these payments monthly until you receive $100,000 per year.’
While he promised her a life of luxury, sources have told Daily Mail Australia he was abusive and controlling of the Californian beauty, whom had travelled to Australia to be his bride in a $3million wedding.
Edelsten owned a Sunseeker Predator, worth millions of dollars
In his prime, Edelsten garaged an Aston Martin DBS Superleggera Volante roadster
He had offloaded a Rolls Royce Phantom Drophead as creditors circled him for missing millions
‘He would telephone (her) more than 100 times a day, often obsessing about (her) whereabouts and what (she) was doing,’ the source said.
Edelsten had told Brynne he would get her a job in the fashion industry and pay for her studies.
She would give up hope as Edelsten trawled the internet for other lovers and subjected her to outbursts of violence.
Daily Mail Australia can reveal Edelsten, who had been hooked on prescription medications, flew into a rage after his ex-wife looked through his phone messages for texts from his other conquests.
Edelsten was accused of chasing his terrified wife around the living room before punching her in the chest, choking her and kicking her out of their apartment.
Those that knew Edelsten best claim he was driven by the public’s perception of him as a big time ladies man.
In reality, he would court various women – including high-priced prostitutes – via a series of online ‘sugar daddy’ websites.
It had been a long time since Edelsten was at his peak in 1984 when he married 19-year old model Leanne Nesbitt.
He bought the Sydney Swans AFL team the following year for $2.9million, making him a household name.
‘I believe much of the spending was driven by ego and (Edelsten’s) desire to maintain a Hugh Hefner-type Playboy image,’ a source told Daily Mail Australia.
Edelsten splashed out on a A Bombardier Challenger jet after selling off his medical empire
Edelsten quickly moved on with another American in Gabi Grecko, who was later caught up in a high flying sex scandal
Brynne and Geoffrey Edelsten make an appearance at the North Melbourne Club’s Breakfast with the Stars event, in Melbourne in 2012 – their relationship was already on the rocks
While declared bankrupt in the US, Edelsten continued to drain a secretive trust account at home.
In Australia, key creditors agreed in 2015 to take just a few cents in the dollar to wipe out more than $20 million of accrued debt.
Months later he would jam a $45,000 engagement ring on the finger of colourful younger woman Gabi Grecko.
Sources have told Daily Mail Australia Edelsten later drove Brynne to bankruptcy in a legal challenge over her marital dues.
‘He embarked on a campaign of what I could best describe as psychological warfare in an attempt to humiliate and destroy (her),’ the source said.
Edelsten hid Brynne’s personal belongings and refused to comply with court orders demanding he provide her ongoing financial support.
Geoffrey Edelsten bought the Sydney Swans in 1985 after making millions in boutique medical facilities. He would be jailed just five years later for hiring a hitman to bash a patient
Leanne Nesbitt (right) married Geoffrey Edelsten when she was 19 and he was aged in his 40s
Brynne had felt she played the important role of ‘loyal wife’ in helping Edelsten secure the sale of his medical empire.
‘She had been the one who had propped the respondent up through the negotiations,’ the source said.
While crying poor to his creditors, Edelston was believed to have still owned a Lamborghini Aventor, Ferrari and various other luxury vehicles.
He had also just cashed in a Sunseeker Predator boat – worth more than $4million – a marina berth in Melbourne’s Docklands, an Aston Martin DBS Volante and a Rolls Royce Phantom Drophead.
Meanwhile, he paid his ex-wife only $18,000 in spousal maintenance while owing her anywhere up to $300,000.
In the years since his ugly fallout with Brynne, Edelston showed little sign that he was short of a buck.
If he ever did hit hard times, the death of his beloved mother Esther in 2016 saw him live the remainder of his years in the lifestyle he had become accustomed to.
Mrs Edelsten had been a millionaire in her own right and owned a multimillion-dollar estate upon her passing.
She had died from cancer, aged 93, in September that year.
Mrs Edelsten had reportedly given her eldest son, who had a history of dating much younger women, one last piece of advice before she died.
‘Choose carefully, don’t keep making the same mistakes,’ she had told him.
Brynne Edelsten leaves a Melbourne court in 2019. She would be bankrupted by her legal expenses fighting for a cut of her ex-husband’s wealth
Geoffrey Edelsten leaves the Melbourne Magistrates court in 2012. He had become a regular face in the court district in the 2010s
Edelsten popped up in news reports the following month claiming he had found love with 26-year-old Playboy model Ashley Kirk.
The following month he was back in court in a dispute with his brother Rodney over their mum’s fortune.
It seemed Geoff had received the lion’s share of it after taking care of their mum in her final years when she was very ill.
Mrs Edelsten had been a former lingerie business owner and dancer.
Her businessman husband, Hymie, who ran the family bicycle-making firm, had died nine years earlier.
Edelsten had shared a close bond with his mum and dedicated his memoir, Enigma, to her.
Little was seen publicly of Edelsten in his final few years of life.
In 2019, he told Daily Mail Australia he was in bed after injuring his ankle in a fall outside his office.
He had been due in court to contest a $3600 fine over an unregistered car.
His court date coincided with his 76th birthday.
‘It’s my birthday tomorrow … I’m going to be 21,’ Edelsten joked.
What remains of Edelsten’s wealth will be the subject of ongoing speculation for months, perhaps years, to come.