Tyrone Vickery's business partner used funds from their restaurant to buy three racehorses, pay trainer's fees and make regular cash advances to gamble at Crown Casino, without the consent of the Hawthorn footballer.
Tony Mokdissi even used a credit card linked to Mr Vickery's restaurant Fat Monkey to buy Louis Vuitton wallets as wedding presents for the footballer and his wife, tennis player Arina Rodionova.
Mr Vickery only discovered he had owned racehorses when a manager came across messages from angry trainers chasing down overdue fees.
A Google search revealed he owned a stake in two mares, Bounty Belle and Streak On, along with an unnamed yearling bought for $5000 from bloodstock agents William Inglis and Sons Limited in April last year.
Mr Mokdissi also provided an associate with Mr Vickery's banking details before giving instructions on how to forge his signature, according to text messages obtained by Fairfax Media.
"Joey, the race is on Saturday. I need those papers lodged today mate ... put a big T V then ickery then side to side."
The associate made several attempts at the Hawk forward's signature, before Mr Mokdissi told him to use the "top one".
On July 5, Mr Vickery and his friend, former Richmond hardman Jake King, were arrested by police over an alleged attempt to recover $150,000 from Mr Mokdissi.
Mr King was charged with extortion, making threats to kill, two counts of threats to inflict serious injury and two counts of using a carriage service to harass. Mr Vickery was released without charge.
It is understood Mr Vickery had discussed the matter with Mr King, who then arranged a meeting with Mr Mokdissi at Crown Casino.
It was at this meeting the threats to kill were allegedly made and covertly recorded.
Mr Mokdissi has family connections to the Comancheros bikie gang through his relative Amad 'Jay' Malkoun who was a Victorian president of the gang but is now living in Greece. Mr Mokdissi had boasted of his gangster connections when working at the restaurant.
Mr Mokdissi, who goes by several first names, has left a string of creditors in his wake following a series of failed hospitality ventures and unsuccessful investments.
One default judgment against Mr Mokdissi in the Magistrates Court last year showed he owed BMW's financing arm $64,327. Another unpaid debt to a food wholesaler totalled $38,859.
In November last year, Cranbourne-based trainer Ricky Maund was pursuing Mr Mokdissi over a $3500 debt.
According to text messages between Mr Mokdissi and Mr Maund the debt was settled using a cheque drawn from Fat Monkey's accounts.
In another message a representative of William Inglis and Son threatened to cancel the sale of the unnamed yearling racehorse when Mr Mokdissi failed to stump up $5000.
"Hi Tony I have left you numerous phone messages and sent you an email as well, this private sale will be cancelled at 5pm today due to non payment," read the message sent on May 25, 2016.
Mr Mokdissi is understood to have used the Fat Monkey credit card to pay for his Christmas holidays in Rosebud last year and made regular $800 withdrawals at Crown Casino.
Mr Vickery last year had to cut short an end of season holiday to Russia and Japan with his wife when the depth of the financial trouble at Fat Monkey was uncovered by a new manager.
The manager had discovered the business was more than $130,000 in debt.
He had found a box of unopened mail which revealed more than $6000 in electricity bills, food suppliers debts, staff who had been unpaid for more than six weeks and rent that was outstanding with court proceedings imminent.
It was at this time Mr Vickery learned that he was an owner of several racehorses and began a forensic audit of the restaurants books with his new manager.
They discovered at least $150,000 that was unaccounted for and believe there was a further $50,000 in cash missing.
The restaurant closed its doors on Monday.
On Tuesday, Mr Vickery's lawyer John Gdanski, issued a letter of demand to Mr Mokdissi for unspecified damages. A formal complaint to police is also expected to be made within days.
Mr Mokdissi did not respond to calls from Fairfax Media. Mr Vickery did not respond to calls for comment.
