“Have myself a Mrs S!” wrote 30-year-old Selwood under the image. At the time of purchase, Selwood was likely unaware that Mr Bensimon is also a bankrupt who racked up personal and business debts estimated at more than $10 million.Mr Bensimon also purchased $641,570 in Crown casino gaming chips, while also losing $693,868 trading derivative contracts and other equities, according to the trustees report.Bensimon Online did not file any defence. Selwood … The magistrate entered default judgment in the company's absence.A table was reserved at Campbell Point House on the Bellarine Peninsula, champagne was put on ice and a photographer booked to capture the moment when Selwood asked the question from bended knee.After the liquidation of several Melbourne-based companies, Mr Bensimon and wife Kate relocated to Sydney's Bondi Beach, where he continues to trade diamonds though companies established by his wife.Selwood launched civil action in the the Melbourne Magistrates Court, which recently ordered Bensimon Online to repay $66,000, along with interest of $1518 and costs of $1967, according to court documents.The flamboyant diamond merchant has also admitted to losing precious stones provided to him on consignment by wholesalers.As his Melbourne-based empire collapsed in 2016, Mr Bensimon was pursued by a string of creditors including diamond wholesalers in Melbourne and Sydney, a former business partner, his sister, a one-time school friend and the Australian Tax Office.The company also claims it agreed to refund Selwood of its own volition."The amount was refunded as mutually agreed to and as per the company returns policy for the reason the client was dissatisfied with the length of time for an adjustment that needed to be made to the ring and decided to purchase a ring elsewhere," the statement says.In a statement, Bensimon Online denies it gave the AFL star a different stone to the one he agreed to buy."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.Selwood and his manager Tom Petroro declined to comment.An investigation by bankruptcy trustees Pitcher Partners attributed some of Mr Bensimon's financial problems to gambling losses totalling almost $2 million with betting agencies TAB, Ladbrokes and Mad Bookie.Selwood has claimed that Bensimon Online had breached the contract of sale.The Cats champion argued in court documents there was a mistake by Sydney-based diamond retailer Bensimon Online, which claims on its website to have sourced "some of the world’s most coveted pieces for clients and celebrities all around the world".In his own affidavit, Mr Bensimon said other diamonds were used as collateral for loans from Melbourne-based lenders, which charged interest of up to 48 per cent a year.In an affidavit filed in the Supreme Court in 2015, Mr Bensimon's father, Eliyahou Ben-Simon, denied any commercial relationship with his son to avoid liability for the massive debts.Geelong captain Joel Selwood is renowned for his meticulous preparation and attention to detail, and his marriage proposal last year to long term partner Brit Davis was no exception.Their business website claims that: "Ron is relentless in his pursuit of sourcing the most exquisite diamonds to design the perfect engagement ring, wedding band or diamond jewellery gift."Bensimon Online is owned by public relations executive Kate Bensimon, but her husband Ron Bensimon is the frontman.According to a series of Supreme Court affidavits, Mr Bensimon conceded he had misplaced a 2.5 carat diamond valued at $63,528.The only flaw with his plan was the round-cut diamond ring that Selwood presented to his future wife was allegedly not the same ring he had agreed to purchase for $66,000.Chris Vedelago is an investigations reporter for The Age with a special interest in crime and justice.