The High Court has made orders winding up two Russian state-owned aircraft and shipping leasing firms, GTLK Europe DAC, and GTLK Europe Capital DAC, which are registered in Ireland.
Mr Justice Conor Dignam said that he was satisfied to appoint liquidators to the insolvent firms after he dismissed their application to be placed into examinership which he said was "fatally deficient."
The companies are worth an estimated €4.11 billion, and their liquidations have been described as the biggest in the history of the State.
The firms, which have been hard hit by sanctions imposed on Russian entities following last year invasion of Ukraine, had launched a bid late last week to be given the protection of the courts from their creditors, several of whom had sought orders to have them wound up.
They had submitted an independent expert's report stating that they could survive as going concerns following a successful examinership.
That proposition, however, was rejected by Mr Justice Dignam.
In his ruling he said the application lacked the "good faith" required to allow a court to appoint an examiner to a company.
The judge noted that the companies had claimed in the examinership proceedings that they were insolvent, which contrasted to the strong denials it had made in its opposition to the winding up proceedings.
This fundamental change of positions, which were contained in legal documents prepared within a relatively short time of each other, needed to be fully explained to the court.
No explanation was given, he said.
The judge also said that the timing of the examinership application, which was brought one working before the High Court was due to hear application to wind up the companies was questionable.
A purported attempt last weekend by the companies, which was done without the knowledge of their Irish lawyers, to have their dispute with the petitioning creditors go before an arbitrator in the UK was also questionable.
He said that the companies had attempted "to derail and delay" the hearing of petitions to have the firms wound up, which commenced before the Irish Courts in April.
The judge also said that the examinership was being dismissed on the grounds that the burden of proof required to show that the company has a reasonable prospect of survival following the examinership process had not been discharged.
The companies, he said, had put information before it, including an independent expert's report, that was "deficient" and "seriously flawed".
There was a lack of financial information, as well as information about the locations, availability and condition of the firms' aviation and shipping assets, the court also noted.
In the circumstances he said that he was dismissing the examinership application and making orders to wind up the companies.
He also said that the court was correct to proceed with the hearing of the examinership petition after lawyers for the companies were allowed to come off record, after their relationship with their clients had broken down.
The judge said the firms had been given the opportunity to address the court after their lawyers indicated that they would no longer act for them in the proceedings but had failed to do so.
The judge handed down his decision on Wednesday afternoon after considering both petitions from several creditors of the company to have the two firms wound up, as well as the company's own application to be placed into examinership.
After striking out the examinership petition the judge proceeded to appoint Damien Murran and Julian Moroney of Teneo Restructuring Ireland appointed as joint liquidators to the companies.
Following the ruling their counsel James Doherty SC said that the issue of sanctions against the Russian-state owned companies was a major issue in the liquidation.
Counsel said that while not wanting to overstep the mark his clients have already been in contact and have had positive discussions with the Central Bank of Ireland, regarding the sanctions.
The court heard that the Kremlin-owned companies have an estimated deficit of over US$1 billion.
The four creditors, represented by barrister Kelley Smith SC, instructed by William Fry Solicitors, that sought to wind up the GTLK firms are Trinity investments DAC and an associated entity Allestor Europe Multi Asset Portfolio which is a sub fund of Allestor Capital ICAV.
The other two creditors are Ben Oldman Special Situations Fund LP and Sona Credit Master Fund Limited which are both registered in the Cayman Islands.
They had opposed the examinership, claiming it was an abuse of process, and said that there had been a "staggering lack of financial information" provided to the court by the companies as part of its application.
The creditors claimed they are owed €162.5m by the GTLK Europe group, and that debt was rising,
GTLK has been hard hit by international sanctions imposed on Russia following the invasion of Ukraine.
GTLK is Russia's largest leasing business in the transport sector and leases ships and aircraft to customers all over the world.
Several directors of GTLK's ultimate parent are government ministers or deputy ministers in the Kremlin.
The creditors claim that the economic sanctions imposed on Russia following the invasion of Ukraine in February 2022 have had "a devastating effect" on the GTLK Europe Group.
GTLK's Europe Group's international leasing business is headquartered in Dublin, and the firms that are sought to be wound up are at the top of the group's structure.
The creditors claim they entered into a series of agreements to refinance the respondent firms' debts, where they advanced significant funds to GTLK Europe Captial, of which GTLK was a co-guarantor.
After the sanctions were imposed the creditors claim there has been significant default by GTLK Europe Capital regarding it repayment obligations, specifically the requirement to repay interest due on the loans.
The matter will return before the court in two weeks' time.