A decades-long friendship has ended in "bitter hostility" due to an $800,000 loan, involving funds to open a wine bar in Europe and import cedar.
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Ivan Kizmann took Gregory De Maine to court seeking repayment of a series of hefty loans.
The men shared a background in the armed services and had been friends for about 20 years.
In an ACT Supreme Court judgment published on Thursday, Chief Justice Lucy McCallum ordered Mr De Maine pay his former friend more than $860,000, plus interest.
"Their relationship now is one of bitter hostility as a result of the events giving rise to these proceedings," Chief Justice McCallum stated.
Starting in 2017, Mr Kizmann made series of loans to his friend in order to support Mr De Maine's "business enterprises".
Mr De Maine had assured Mr Kizmann he would repay the loans, including interest, within certain periods of time.
However, as time went on, Mr De Maine became evasive, saying he was too much in debt to make any repayments.
"He blamed unforeseen difficulties for his straitened circumstances and even accused Mr Kizmann of being greedy for seeking repayment," the Chief Justice said.
In court, Mr De Maine had contended the funds were advanced not to him but to his now deregistered company, Shostko Systems Pty Ltd.
Chief Justice McCallum rejected this claim and found the money had been borrowed by Mr De Maine personally.
"[At the time] discussions [between the friends] were underpinned by mutual trust and unarticulated assumptions," she said.
"By contrast, their exchanges since their friendship has soured have been marred by vitriol in measure equal to the trust they once shared."
In November 2017, Mr Kizmann lent his friend 125,000 Euros to open a wine bar in Prague.
Mr Kizmann recalled his friend saying if he lost his job: "I've got wine valued at $600,000, I'll just sell the wine stocks and sell the wine bar and pay you back."
During this time the two men discussed people who were buying Porsches and Lamborghinis.
In 2018, Mr De Maine sent a message to the other man on WhatsApp saying: "If you help us build our global business I will buy you a yacht."
"The WhatsApp chat saw many such friendly exchanges while times were good," the judge stated.
A second loan involved $50,000 in three separate advances.
Mr Kizmann had said in December 2017, Mr De Maine asked for more money with the initial payment not having come through.
A third advancement involved $55,000 to import cedar into Australia.
Mr De Maine had claimed there would be a $200,000 profit per container and the Russian government would take the timber if he didn't "lock in a deposit".
The money was transferred on April 26 in 2018.
In May the same year, Mr Kizmann loaned his friend more than US$55,400 for more cedar.
By 30 May, 2018, Mr De Maine said "all will be lost" if he didn't get funds to clear timber shipments from customs.
Mr Kizmann then lent his friend another almost 28,000 Euros, the last of his money which he said he needed to live on.
Mr De Maine said "you'll get your money back even if I have to work for the next 10 years. I'll never forget this".
