Businessman Seán Quinn, his son Seán and nephew Peter Darragh Quinn have been found to be in contempt of court at the High Court for putting assets beyond the reach of the Irish Bank Resolution Corporation.
The IBRC, formerly Anglo Irish Bank, accused them of taking steps to put the Quinn Group's international property assets out of the reach of the bank, after the court granted injunctions preventing them from doing so.
IBRC is currently chasing €2.8bn in debts from the group.
The court will hear arguments on Friday morning about what should happen next, but Ms Justice Elizabeth Dunne said it would be difficult to persuade her that there should not be a punitive element, as well as a coercive element to whatever action she takes.
Ms Justice Dunne said she was not impressed with the manner in which the three men gave evidence.
She said Peter Darragh Quinn was evasive, obstructive, uncooperative and, at times, untruthful and she came to the conclusion that he would have said and done anything to aid the plan he conceived to put assets beyond the reach of Anglo.
Ms Justice Dunne said Seán Quinn Snr was also evasive and uncooperative and that on a number of occasions during the hearing, rather than answer questions put to him, he embarked on lengthy criticisms of Anglo.
She said she found it impossible to accept his evidence that he had no hand, act or part in the matter after April 2011 following the appointment of a share receiver.
She said his evidence to that effect was not credible.
The judge said she was satisfied that he gave his nephew his imprimatur to implement the plan, and that he took whatever steps were required of him by signing documents as required when necessary.
She said she was satisfied beyond any doubt that he was fully supportive of it and actively involved in doing what was required to implement the plan as and when necessary.
Ms Justice Dunne found that Seán Quinn Jnr was not telling the truth in giving his evidence to the court.
She said Seán Quinn Snr spoke of the honourable respectable way in which the businesses in the Quinn Group were run and she wished she could say the same about the manner in which they had dealt with the adverse circumstances in which they now found themselves, having regard to the collapse of the Quinn business empire.
Ms Justice Dunne said there was a dispute between Anglo and the Quinns about Anglo's ability to recover a sum of around €2.8bn.
But she said it had never been in dispute that a sum of around €455m was due to Anglo.
Instead of trying to repay the admitted debt due, the Quinn family and in particular the three men in the contempt proceedings, had taken every step possible to make it as difficult as can be to recover any amount due.
Ms Justice Dunne said they had engaged in a complex, complicated and no doubt costly series of steps designed to put the international assets beyond the reach of Anglo in a blatant, dishonest and deceitful manner and had consciously misled courts in Ireland and elsewhere.
She said the behaviour of the respondents outlined in evidence before her was as far removed from the concept of honour and respectability as it is possible to be.
She will hear arguments on Friday about what steps should be taken next.
The judge said she would have thought that the coercive element should be to the fore, given the aims of the bank and what this was all about.
She told lawyers for the Quinns that the punitive element would be influenced by the level of cooperation from the Quinns in relation to any coercive order that might be made.
But she said having regard to all the circumstances, it would be difficult to persuade her that there should not be a punitive element as well as a coercive.
The bank is to let the Quinns know by 8pm tomorrow, what it intends to ask the court to do.
The possible penalties for contempt of court include imprisonment and fines.
Asked outside court what his reaction to the judgment was, Seán Quinn Snr said it was "interesting, very interesting".
He said he was not dishonest.