Developer Paddy McKillen has lost his legal challenge to the National Asset Management Agency.
The three judges of the Commercial Court ruled against Mr McKillen on all five grounds on which he based his case.
Mr McKillen had argued that NAMA had failed to take into account relevant considerations - such as the fact that his loans were performing and that only a quarter of his assets were in Ireland.
The court found that any discretion given in the legislation to NAMA to decline to acquire eligible bank assets was discretion solely for the benefit of NAMA.
It also found the legislation did not require NAMA to carry out a detailed analysis of the loans.
The court ruled in relation to Mr McKillen's claim that his constitutional right to fair procedures was denied, any constitutionally protected rights he might have were either not interfered with by the act or interfered with in such a minor way as not to require Mr McKillen to be heard before his loans were acquired.
Mr McKillen also claimed the decision was made to transfer his loans before NAMA was officially established.
The court also found that the decision taken to transfer Mr McKillen's loans, which was made on 11 December and 14 December, was adopted by subsequent action of NAMA following its establishment on 21 December.
Mr McKillen was trying to stop more than €2bn of loans being transferred to NAMA.
He claimed all his loans were performing and that his business would be damaged if they were transferred.
Mr McKillen claimed NAMA did not take factors like these into account and had denied him fair procedures.
The developer claimed only impaired borrowers could be taken in, according to the European Commission and he claimed the NAMA legislation was unconstitutional.
However, the court ruled that the European Commission's decision approving NAMA did not limit the agency to taking in impaired loans.
The court concluded that the NAMA Act is a proportionate response to the very grave financial situation in which the State finds itself.
Mr Justice Nicholas Kearns said the court was not concerned with deciding whether the policy options adopted by the Oireachtas as a solution to the banking crisis were the best solutions.
He said the court was concerned with the question of whether there was a rational basis for the selection of those options and he said the court was satisfied there was such a basis.
NAMA's legal team was led by the Attorney General and told the court Mr McKillen's case did not stand up.
NAMA argued leaving Mr McKillen's huge portfolio of loans on the books of the banks could have undermined the whole purpose of the agency.
The court heard many of Mr McKillen's loans had expired and were due to be repaid.
The three judges were told there was no flaw in the original decision as it was part of an ongoing process.
In a statement, NAMA chairman Frank Daly said: 'Clearly this has been a very significant case and we will study the decision of the Court closely over the coming days.
'However it is clear that the decision highlights the critical importance of the work of the agency for Ireland and the extraordinary circumstances which led to its establishment.
'As a board and cognisant of the Minister for Finance's statement of 30 September we will continue to focus on the task in hand which is to complete the acquisition of eligible assets from the five participating institutions with the objective of maximising the return for the Irish taxpayer from those debtors whose loans NAMA has acquired.'
Lawyers for Mr McKillen indicated they may bring an application for leave to appeal the decision to the Supreme Court on Friday morning.
Under the NAMA Act, there cannot be an appeal to the Supreme Court without permission from the High Court.
The Act also states that the court shall only give permission for an appeal if it decides that its decision involves a point of law of exceptional public importance and that it is desirable in the public interest that an appeal should be taken to the Supreme Court.
