The former head of defunct construction firm Red Sky was declared bankrupt today over alleged debts of nearly £17 million.
An order was made against Norman Hayes at the High Court in Belfast following a petition by the Northern Bank.
The bank brought proceedings claiming it was owed millions of pounds on a series of personal guarantees.
Mr Hayes, described on court papers as a businessman of Quarry Road, Belfast, was managing director of Red Sky until it went into voluntary administration in 2011.
It followed a decision by the Northern Ireland Housing Executive to cancel maintenance contracts with the firm over concerns about work practices.
In its bankruptcy application the bank listed five personal guarantees between 2006 and 2008 it said formed part of Mr Hayes' debt.
They included nearly £7m in total for lending facilities provided to the Red Sky Group.
A further £6.59m was linked for to Rivermount Developments Ltd.
Another £646,000 was for facilities the bank provided to Ramparts Holding Company Ltd.
The bank has also attempted to claw back nearly £2.56m on a series of accounts, according to the papers.
Its petition stated that despite formal demand letters the money remains due.
"The above-mentioned debt is for a liquidated sum payable immediately and the debtor appears unable to pay it," it claimed.
Mr Hayes' centre of main interests were listed as Quarry Road and the offices of Totalis Solutions Ltd, Grove Street East, Belfast.
The Northern Ireland Court Service confirmed a bankruptcy order had been made against the businessman.