Creditors and an ex-business partner are reportedly set to challenge Geoffrey Edelsten's will in an attempt to track down millions of dollars in debts.
The controversial businessman and former owner of the Sydney Swans died last week at the age of 78.
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He was reportedly found by his cleaner in his St Kilda Road apartment, with Victoria Police saying a report would be prepared for the coroner.
The death is not being treated as suspicious.
Edelsten is said to have left a string of debts across the world, despite making $100 million after selling his Allied Medical Group - a chain of GP clinics.
He owned mansions, helicopters and a fleet of expensive cars with licence plates emblazoned with "macho", "spunky" and "sexy".
The 78-year-old claimed bankruptcy in both Australia and the United States in 2014, citing a number of bad business deals including "splurging" millions on ghetto estates going cheap during the US mortgage crisis.
By 2016 he was being chased by more than 40 creditors in Australia and the US, including the Australian Taxation Office, for millions of dollars.
Multiple parties, including former US business partner Rafael 'Alfie' Mawardi, are now expected to make a claim on his estate.
Mawardi told the Herald Sun he never saw a cent from Edelsten despite having invested more than $20 million into Mawardi's 'House of Nurielle' fashion boutique.
“I’m sure there is still money out there,” Mawardi said.
“He had all the cars, he had 10 to 15 cars – are you going to tell me that it all just disappeared?
“I think that now that he has passed away, I have legal rights to go after him.”
According to the Herald Sun, Edelsten's first wife Leanne Nesbitt, former girlfriend Isabel Beard and their love child Matthew Beard, Edelsten’s second ex-wife Brynne and estranged wife Gabi Grecko may also have a claim to his estate.
Lindsay Hosking, who had worked as Edelsten’s long-time accountant, told the Herald Sun he had been appointed the executor of Edelsten's will but he had “no idea” if anyone would challenge.
Geoffrey Edelsten's colourful and controversial life
Edelsten set up a string of open-all-hours medical clinics in the 1980s that featured grand pianos and chandeliers in the waiting rooms. Patients, who were bulk-billed, flocked to the clinics.
But he was deregistered in NSW in 1988 and later in Victoria and spent time in jail, found guilty in 1990 of soliciting a well known hit-man, Christopher Dale Flannery, to assault a former patient.
He became, by his own description, a "white knight" of the Swans in 1985 as they faced dire financial pressure and concerns they couldn't survive.
He published a book in 2011 titled "Enigma", covering his life as a musical entrepreneur, career as a country doctor and city businessman.
But it was his relationships with pretty young blondes that kept him in the spotlight.
He divorced first wife Leanne, a model, in 1988 after a three-year marriage, then married American fitness instructor Brynne Gordon in 2009 when she was 40 years his junior.
Less than a year after Brynne called things off in 2013, Edelsten proposed to American model Gabi Grecko, 46 years his junior, at the Melbourne Cup.
But their love bubble burst not long after, with claims of infidelity on Edelsten's behalf and a range of public spats.
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