Lawyers for John Gilligan have argued in the Supreme Court that the Criminal Assets Bureau seized properties from him without a proper hearing.
CAB seized three properties from Gilligan in 1996, including a house beside the Jessbrook Equestrian Centre in Co Kildare.
He was released from prison in 2013 after serving 17 years behind bars for drug trafficking.
Today, his legal team argued that the assets were taken without a proper hearing first to prove if they were the proceeds of crime.
Lawyers for CAB argued that this issue had not been raised before at numerous different hearings so could not be raised now.
They described it as an ‘’Alice through the looking glass’’ appeal.
Chief Justice Susan Denham criticised Gilligan's lawyers for their legal papers, saying they were in "a disgraceful state" and adding to the court's workload.
The case is due back before the Supreme Court tomorrow.