Joe O'Reilly, the developer of Dundrum Town Centre, is in "ongoing discussions'' with his lenders after one of his companies reported "significant losses''.
It has also emerged that Bank of Ireland lent money to Mr O'Reilly for land in Skerries, Co Dublin, just as the financial crisis was starting.
Many of Mr O'Reilly's firms are unlimited and don't have to file accounts, but an auditor's report for a company called Teba Ltd filed this week disclosed that this firm "incurred significant losses" in the year to the end of December 2009.
The company's balance sheet was insolvent at the end of December 2008 and an EGM may be needed, according to auditors BDO.
"Ongoing discussions are taking place with the company's lenders regarding the company's borrowings. The company's ability to continue as a going concern is dependent on the continued support of its lenders," state the auditors.
"The balance sheet shows an excess of liabilities over assets,'' they add.
Mr O'Reilly is most associated with two companies -- Chartered Land, a commercial development company, and Castlethorn Construction, a residential house builder, most associated with Adamstown, near Lucan, Co Dublin.
Chartered Land, set up only five years ago, is behind some of the largest retail complexes in the country, including the Pavilions in Swords and the Dublin Central Scheme, due to open on O'Connell Street in 2013 at a cost of €1.25bn.
Anglo Irish Bank is a major backer of Mr O'Reilly, having provided his firms with loan finance over recent years, according to land registry records.
Mr O'Reilly's loans moved into NAMA in the first tranche of transfers.
Records also show that Bank of Ireland completed a loan facility with Mr O'Reilly in August 2007 for land in the Skerries area.
The Irish Independent recently revealed that fresh planning permissions for the giant Adamstown development are also being sought by Mr O'Reilly's firms.