Convicted drug dealer John Gilligan has claimed before the Supreme Court he did not receive a proper trial when his assets were frozen by the State in 1996.
As a result, his lawyers say, subsequent court rulings based on that decision were flawed or invalid.
He wants a five-judge Supreme Court to re-visit its 2008 decision declaring certain of his assets, and those of his family, came from the proceeds of crime.
The Gilligan family is also appealing a 2011 High Court ruling certain of his assets and those of his family are forfeit to the State.
The property included the Jessbrook equestrian centre in Enfield, Co Meath, which Mr Gilligan bought and developed before he spent 17 years in prison for drug trafficking.
Other property owned by his former wife Geraldine, daughter Tracey and son Darren, was also found to be the proceeds of crime.
The Gilligans claimed the properties were bought from legitimate earnings but the High Court ruled in 2011 their explanations were incredible and improbable.
All four members of the family, represented by three Queen’s Counsel from London, were in the Supreme Court on Tuesday for their appeal aimed at overturning the previous proceeds of crime orders. They were previously granted legal aid for the appeal.
They are also bringing a challenge claiming their rights under the Constitution and European Convention on Human Rights have been breached.
The Criminal Assets Bureau (CAB), which obtained the orders and has since sold off the Enfield equestrian centre, disputes they have any right to bring a further appeal.
The issues have been determined on three separate occasions by the courts and this appeal fails to meet the exceptional circumstances test for the Supreme Court to re-visit a decision, CAB argues.
Michael Bromley-Martin QC, presenting the case for all the family in relation to the 2011 High Court decision, said the family never got an opportunity in 1996, as provided for under Section 3 of the Proceeds of Crime Act 1996, to challenge the basis on which CAB applied to freeze the assets.
This meant all subsequent court decisions were not valid, counsel said.
The effect of the freezing orders was the Gilligans were deprived of property they lawfully owned without having had a trial of the proceeds of crime issue, he argued.
That trial would have needed to have met a number of requirements, he also submitted. The Gilligans were entitled to reasonable time to prepare their case, an opportunity to be present, to have legal representation, to cross-examine witnesses and to have the trial held within a reasonable time.
John Hardy QC, presenting the case for the Supreme Court to revisit the 2008 decision, said the matter met the exceptional circumstances test.
Asked by Mr Justice William McKechnie was he saying the 2008 Supreme Court decision was self contradictory and inherently inconsistent, Mr Hardy said: “Yes”.
It was necessary the matter to be clarified so citizens may know what is lawful and what is not, he added.
Ben Ó Floinn BL, for CAB, said this “extraordinary application” had something of an “Alice Through the Looking Glass” feel to it. The 1997 order on which subsequent court decisions were based was valid, he said.
The Gilligans had ample opportunity over several years to present their case and were now seeking to raise arguments they had not raised before the High Court, he argued.
At the outset of the hearing, Chief Justice Mrs Justice Susan Denham, on behalf of the five-judge court, said the papers presented to the court were in a "disgraceful state".
They were too long, repetitive, the index was not helpful and all that greatly increased the work of the court in the appeal, she said.
Mr Bromley-Martin said there were considerable attempts made to control the amount of paperwork and to avoid duplication.
The hearing continues.