The National Asset Management Agency has secured a summary judgment of €29m against businessman David Cullen over outstanding loans for properties including the Turk's Head Bar and Paramount Hotel in Dublin's Temple Bar.
Mr Justice Peter Kelly ruled Mr Cullen had no defence to the agency's claim.
Judge Kelly also refused to grant a stay on judgment pending consideration of an appeal.
The decision means NAMA can now take steps recover the money owed.
Lawyers for NAMA had opposed a stay as a decision is due on 9 April on Mr Cullen's application for bankruptcy in England.
They said NAMA's application for summary judgment had already been delayed by "meritless" points raised by Mr Cullen and a stay could affect the Irish court proceedings if Mr Cullen were declared bankrupt in the interim.
Mr Cullen had argued he had an arguable defence to the application by NAMA for summary judgment.
In 2010 the agency took over the loans given by Bank Of Ireland from 2002.
The loans were for a number of purposes including development of the Turk's Head and Paramount Hotel and the Seafield Hotel and apartments in Ballymoney, Co. Wexford.
Mr Cullen is now living in London.
Mr Justice Kelly said it was very clear he had no defence to summary judgment.
He rejected claims by Mr Cullen that he had been given minimal opportunity to make representations before his loans were taken over.
He also rejected other claims that NAMA did not have the legal standing to bring the case or that the loan facilities were not "eligible bank assets" within the meaning of the NAMA Act 2009.
Mr Cullen had argued some of the loans were made for multiple purposes but the judge ruled whether or not the purpose of each of the loans was expressly related to development land, the breadth of the definition of eligible bank assets captured all the loans.