Property developer Sean Dunne's Irish bankruptcy has been extended for 12 years by the High Court, in a ruling describing him as "deeply dishonest".
Ms Justice Caroline Costello made the order over what she described as Mr Dunne's "wilful and deliberate" failure to cooperate with the court official administering his bankruptcy.
She said she found it difficult to conceive of a bankrupt who could be more obstructive and less cooperative with the bankruptcy process.
The judge said she had no hesitation in concluding he had failed to cooperate and had failed to disclose or had hidden information about assets from the Official Assignee, Chris Lehane.
She also found the breaches of his statutory duties under the Bankruptcy Act were extremely grave, serious, persistent and deliberate.
In a statement issued by lawyers on his behalf, Mr Dunne described the ruling as "extraordinary".
He was due to exit bankruptcy in July 2016 and will not now do so until April 2028.
He said he was "deeply disappointed and shocked". He also considered the judgment had failed to address adequately the issues of dual bankruptcy in Ireland and the US.
The statement said he intended to appeal the ruling as soon as possible.
Ulster Bank had petitioned the High Court to have Mr Dunne adjudicated a bankrupt in February 2013 after he had defaulted on loans of around €164 million.
A month later, Mr Dunne filed for bankruptcy in Connecticut, claiming to have debts of €1 billion and assets of €55m.
The US court appointed a US bankruptcy trustee. Mr Dunne was adjudicated a bankrupt in Ireland in July 2013.
Mr Lehane brought proceedings opposing Mr Dunne's automatic discharge from bankruptcy to allow further investigations.
Mr Lehane said he had yet to receive necessary information he had sought from Mr Dunne. Mr Dunne strongly opposed the application to extend his bankruptcy.
Ms Justice Costello, however, said it was difficult to conceive of a more thorough determination not to cooperate with the process and to seek to conceal and hide assets.
She said there was a "cynical, spurious attempt" to preserve the illusion of cooperation in order to achieve a discharge.
The judge noted that Mr Lehane had described Mr Dunne as the most duplicitous bankrupt he had ever encountered and two judges in his US case had also described him as non cooperative.
She said he remained unrepentant, knew exactly what he was doing and was determined at all costs to conceal as much information as possible from the Official Assignee.
She said Mr Dunne had likened Mr Lehane to a bounty hunter, but that was not the case, and he was simply trying to carry out his statutory obligations.
She said Mr Dunne had actively and intentionally misled the Official Assignee about matters related to the ownership and control of a valuable property on Shrewsbury Road.
Mr Dunne claims he bought the house "Walford" for €58m in 2005 in trust for his wife, Gayle, and that issues concerning its sale and ownership remain to be decided in other court proceedings.
Ms Justice Costello also described claims maintained for a time by Mr Dunne that his principal address was an unfurnished, for sale property in Connecticut, as "at best disingenuous".
She said Mr Dunne had unilaterally decided what information he would provide, what sections of laws he would abide by. She said his actions had affected creditors by adding greatly to the costs of administering his estate.
The High Court can extend a bankruptcy by up to 15 years if it considers that necessary. The judge said she would extend it to 29 April 2028.
She also ordered Mr Dunne to make monthly payments of €7,000 until 25 May 2021.
