Patrick 'Dutchy' Holland has lost his High Court application to challenge the 12-year jail sentence he received for drug running.
Holland (66) claimed he was being unlawfully detained in Portlaoise Prison for possession of cannabis, valued at the time at around £100,000.
Holland's legal team argued that warrants issued for his detention had errors. They argued dates on the warrant sheets were incorrect, making the detention invalid.
They also claimed the Director of Public Prosecutions did not grant special leave to hear Holland's case in the Special Criminal Court.
Mr Justice Paul Gilligan refused the application. He said he was satisfied all the matters raised by Holland's lawyers should have been taken into account during his trial and were matters appropriate to his appeal.
"In my view they are matters which are irrelevant to the applicant's present detention in Portlaoise Prison because he is detained in Portlaoise Prison pursuant to the detention order of 28th day of November, 1997," the judge ruled.
"In any event notwithstanding these views the applicant does not make out a case that the relevant provisions of Section 48 of the Offences Against the State Act 1939 were not complied with but merely makes the case that there is no evidence that they were complied with. In these circumstances I decline to grant the applicant leave to apply for the relief as sought on the grounds as set out."
Holland has served seven years of a 12-year term. In November 1997, he was sentenced to 20 years' imprisonment by the non-jury Special Criminal Court for possession of cannabis with intent to supply.
The sentence was reduced to 12 years by the Court of Criminal Appeal in June 1998 and he is due for release next April.