Dublin criminal Martin Foley, who is known as "the Viper", has lost an appeal against the Criminal Assets Bureau demanding tax and interest payments of almost €750,000.
The 66-year-old has been ordered to pay CAB a tax and interest bill of over €738,000 for the years 1993/94 and 1999/2000.
Foley claimed he had been "taken by surprise" by the proceedings and was prejudiced because of an "inordinate and inexcusable delay".
However, the Court of Criminal Appeal found that he had "no case" and dismissed his appeal.
CAB will now seek to enforce the order and collect the outstanding tax.
Martin Foley is a long-time and well-known Irish criminal who has over 40 criminal convictions.
He has been shot several times and survived a number of attempts on his life.
He was also a member of the late Martin Cahill's criminal gang.
Cahill, who was known as 'The General', was shot dead in 1994.
Foley was rescued by gardaí after he was abducted by the IRA in 1984 but refused to co-operate with gardaí.
More recently he set up a debt collection agency called Viper Debt Recovery and Repossession Services.