A $45m property debt was transferred from one of Seán Quinn's companies to put it beyond the reach of a creditor bank, a Belfast High Court judge ruled.
Mr Justice McCloskey held that those responsible for the loan assignment over a Ukrainian shopping centre were "indulging in an orchestrated, elaborate and illicit charade".
He is now set to declare all disputed transactions null and void and return control to the former Anglo Irish Bank.
His ruling strengthens the renamed Irish Bank Resolution Corporation's overall attempt to recoup more than £2 billion it claims to be owed.
Proceedings were issued against the British Virgin Islands-registered Lyndhurst Development Trading in order to seize control of the mall in Kiev.
The bank claimed assets were stripped to prevent it securing money it owed to it.
A chain of loan assignments were under scrutiny in the case.
Fermanagh-based firm Demesne Investments, of which Mr Quinn is a former director, had been owed $45m by Univermag, the Ukrainian owners of the shopping centre.
But in April 2011 Demesne transferred its rights to the debt to Innishmore Consultancy, another Northern Ireland company run by Mr Quinn's nephew Peter Quinn. From there the loan was transferred on to Lyndhurst last October.
Lawyers for IBRC argued that the assignment was a sham, carried out at a massive undervalue and not worth the paper it was written on.
No defence was offered in the case after Lyndhurst's legal team came off record.
Delivering judgment today, Mr Justice McCloskey said: "The abrupt, unexplained and prima facie irrational assignment of a company asset, the $45m debt of which Demesne was the beneficiary, for nothing, or at most something truly minimal, speaks for itself.
"When considered in conjunction with the other related impugned transactions, it is patent that the participants were indulging in an orchestrated, elaborate and illicit charade."
"Based on the available evidence, this exercise had no purpose other than to put this asset beyond the reach of legitimate creditors and/or to prejudice their interests," he added.
According to his assessment the bank were the victims of the assignments and eligible for an appropriate remedy.
An order is expected to be drawn up next week which will declare all of the disputed transactions null and void.
Demesne is set to be confirmed as solely entitled to the debts, thus putting them back within the reach of the bank.
Quinn claims IBRC doing everything it can to destroy him
Bankrupt businessman Seán Quinn said he was unaware of the corporate structures set up to hold international property assets for his children.
The High Court heard this was despite the fact that he swore a document during his bankruptcy proceedings in the North outlining those structures.
Mr Quinn said he was not involved in the administration of his business. He said he was dealing with making money.
He agreed he had acknowledged that he owed €455m to Anglo which had been advanced for the purposes of the international property portfolio.
Bankrupt businessman Seán Quinn said he was unaware of the corporate structures set up to hold international property assets for his children.
The High Court heard this was despite the fact that he swore a document during his bankruptcy proceedings in the North outlining those structures.
Mr Quinn said he was not involved in the administration of his business. He said he was dealing with making money.
He agreed he had acknowledged that he owed €455m to Anglo which had been advanced for the purposes of the international property portfolio.
Lawyers for IBRC said he had acted to remove from the international companies the ability to pay back the money.
Mr Quinn agreed it was correct that he and his family had been trying to ensure money owing in relation to these investments would not be available to repay Anglo.
Mr Quinn said he did not know the details of a plan to sell international assets to third parties who would then sell them on to offshore companies controlled by the Quinn family. He said he had no idea about this.
The businessman said his ambition was to get the assets out of the grip of a reckless bank which had destroyed him and his company. He said he did not care how his family did it.
Mr Quinn said Richard Woodhouse of IBRC was pursuing him to the death and was very vindictive. He said the bank overturned his bankruptcy after he had created 7,000 jobs and put surveillance and security on him by people carrying guns.
He said the bank was doing everything in its power to try to destroy him and his family.
Despite 30 years of war in the border counties, he said there had never been any trouble in Derrylin until Anglo came in.
''This had never happened in the history of the state where someone comes in to rape your company,'' he said.
Ms Justice Elizabeth Dunne said these were not matters she had to make a decision on.
She told Mr Quinn that may be one day he would be proved right but she was not concerned with these issues and asked him to answer the questions asked by lawyers for IBRC.
