When The Bachelor's Sam Wood proposed to Snezana Markoski with a $50,000 diamond engagement ring last year, neither of them could have known the massive rock still actually belonged to someone else.
The story of how Sam picked the ring began with a secret meeting between the 'bachelor' and Melbourne diamond merchant Ronnie Bensimon in a Crown Casino hotel room.
The flamboyant jeweller had a well-earned reputation for the personal touch among his upmarket clientele, who are said to include casino high-rollers and celebrities Nicole Trunfio, Pia Miller and Whitney Port.
Away from the prying eyes of the media, Sam selected a two-carat stone and the Bensimon team worked frantically to ensure it was ready for the reality TV couple's big moment.
It was a major publicity coup for Mr Bensimon, but behind the scenes his business empire was in dire trouble.
By the time it collapsed six months later in mid-2016, Mr Bensimon had amassed personal and business debts estimated to be worth more than $10 million.
It turned out that Snezana's stone was one of more than a dozen diamonds Mr Bensimon's had obtained from other dealers or accepted for sale on consignment but whose owners would allegedly never be paid.
Some of the jewels ended up as collateral for high-interest loans; others have simply disappeared.
After once leading a lifestyle befitting the Kardashians, the 38-year-old is now being chased by a string of creditors including diamond wholesalers, a former business partner, his sister, a one-time school friend and the Australian Tax Office.
Victoria Police have been asked to investigate the disappearance of the diamonds, while at least one disgruntled creditor has approached an underworld figure to recoup a sizeable debt from Mr Bensimon, who claimed to have just 17 cents in his bank account when he declared personal bankruptcy in late July.
Before external administrators were called in, Mr Bensimon owned jewellery stores at Crown Casino and on Elizabeth Street, as well as an online retailer.
On his now-defunct website, Mr Bensimon once boasted that dealers were happy to loan him diamonds "without so much as a handshake".
"It's that part of the industry which Ron admires; that although the world changes around it, the part of the diamond industry he operates in is built on gentleman's (and gentlewomen's) agreements," the marketing blurb boasted.
But while his clients paid for their diamonds, Mr Bensimon allegedly did not.
According to a series of Supreme Court affidavits, Mr Bensimon received about 12 diamonds between September 15 and December 24 last year from wholesaler Australian Diamond Trading Corporation.
ADTC owner Paul Ivany declined to comment, but the diamonds were provided on consignment, which allowed the gems to be exhibited to prospective buyers and returned if they failed to sell.
Mr Bensimon had similar arrangements with other wholesalers and private dealers in Melbourne, Sydney and overseas.
In his own affidavit, Mr Bensimon said he used the gems as collateral for loans from Melbourne-based moneylenders, iBorrow and Sell Your Gold, which charged interest of up to 48 per cent a year.
He claims the funds were transferred back to his businesses to cover general business expenses and debts.
But he also conceded that a 2.5 carat diamond valued at $63,528 had been lost.
"I do not know the current location of [the diamond] or who has possession of it."
He claims other diamonds were sold through his stores, but "I am unable to recall when, to who and in which store each of them was sold".
Mr Bensimon also obtained a 5.13 carat diamond from Australian Diamond Trading Corporation that was supposedly intended as a replacement stone for his wife's engagement ring.
But after purchasing it on invoice at a discounted price of $150,000, the stone was ultimately used to secure another high-interest loan from Sell Your Gold.
Owed about $1.4 million, ADTC launched court action to restrain iBorrow and Sell Your Gold from selling the stones, which ranged in value from $2781 to $107,892.
However, Sell Your Gold owner Alejandro Mendieta claimed in an affidavit the diamonds had already been returned to Mr Bensimon.
Mr Mendieta also claims to still be owed money, but he will have to join a conga line of creditors in the wake of Mr Bensimon's bankruptcy and business failures.
Mr Bensimon agreed to buy out his business partner for $3.1 million in May 2015, but has only paid about $300,000 despite repeated assurances the deal would proceed.
Older sister Nicole Tugendhaft loaned Mr Bensimon $1 million on October 2015, but was never repaid.
In February 2016, Mr Bensimon persuaded a former schoolmate from Mount Scopus College to invest $741,000 in a plan to sell diamonds overseas.
The man was shown the jewels at an underground bank vault in the CBD and told he could expect a $125,000 return on his investment.
Even though the jewellery business was on the brink of collapse, Mr Bensimon, his wife and their daughter then flew first class to Thailand, Hong Kong, the United Arab Emirates, France, Switzerland and England on a five-week trip.
They attended jewellery shows and regularly posted photographs on social media of themselves in opulent hotel rooms, relaxing by the pool or shopping at Dior.
His former schoolmate received less than $100,000 and it remains to be seen if any diamonds were ever sold.
An investigation by bankruptcy trustees Pitcher Partners has attributed some of Mr Bensimon's financial problems to gambling losses totalling almost $2 million with betting agencies TAB, Ladbrokes and Mad Bookie.
Mr Bensimon also purchased $641,570 in Crown Casino gaming chips in the past two years.
He also reached limits on credit cards and overdraft facilities with five different banks to run up debts of $76,616, while another $693,868 was lost trading derivative contracts and other equities.
In a desperate bid to resurrect his fallen empire, Mr Bensimon has unsuccessfully approached several members of Melbourne's Jewish community over the past few months in a bid to secure short-term funding.
He was also knocked back by an underworld loan shark.
Mr Bensimon's business failures have angered his father, who sold the family jewellery business to his son in 2013.
In an affidavit filed in the Supreme Court, Mr Bensimon's father, Eliyahou Ben-Simon, was forced to deny any commercial relationship with his son to avoid liability for the massive debts.
"I am bitterly disappointed and embarrassed at the way my son appears to have conducted the business since his company bought it," Mr Ben-Simon said.
But despite his dire financial situation and status as a bankrupt, Ronnie Bensimon continues to trade diamonds though a company established by his wife, Kate Bensimon.
They recently launched a new website spruiking their "unique passion and an unparalleled approach to working with diamonds, having sourced stones and creating unique jewellery pieces and engagement rings for clients and celebrities all over the world".
Mr Bensimon refused to respond to questions from Fairfax Media.
"You don't have all the facts, that's all I'm going to say," Mr Bensimon said.
"I have spoken with my legal representation and been advised that I am not in a position to go on the record about information that has been unlawfully obtained by The Age."