Adrian Nicholl controlled the Network Trading Group which was based at Bridge Street in Banbridge and owed the sum to Bank of Scotland (Ireland).
The group, which owned properties in Portadown, Larne, Lisburn, Dunmurry, Belfast and Culcavy, went into administration in October 2010.
Another of Mr Nicholl’s companies, Sonah (NI) went into liquidation that year also.
Sonah (NI) ran the Highways Hotel in Larne and was said to owe more than £1m.
Mr Nicholl was also the chairman of the Portadown charitable company, the Thornton Trust, which is being liquidated.
The trust collapsed in 2010 with debts estimated at more than £12m.