GERRY Conlan was one of Ireland's high rollers who went from pocketing hundreds of millions from the sale of a business park in 2006 to being described in court a few years later as having "no money".
The sale of the 400-acre Millennium Park site in Naas, Co Kildare -- which he owned with another local developer Dermot O'Rourke -- for €320m was the most expensive land deal ever done in Ireland.
It catapulted the property developer into the ranks of Ireland's super-rich, and made him one of the most sought-after and powerful customers of the country's banks.
As well as developing property, Mr Conlan has also built up a private hospital empire that includes Mount Carmel Hospital in Dublin, St Joseph's in Sligo and Aut Even in Kilkenny.
The 46-year-old, who lives with his family at Fournaughts in Naas, was described in the Commercial Court earlier this year as one of AIB's most prized customers at the height of the boom.
The bank gave him a total of €313m worth of loans, exceeding its own limits to individual borrowers.
At the time, he gave the bank a €127.5m personal guarantee that the loans would be repaid.
And he was also one of Anglo's treasured clients.
Its former boss David Drumm knew he could rely on Mr Conlan to help save the bank from imploding in 2008 -- by signing up to take out loans to buy some of Sean Quinn's stake.
The extent of Mr Conlan's AIB bank debts tumbled out during a lengthy court case taken by former One51 boss Philip Lynch and his family this year against AIB and two law firms, LK Shields and Matheson Ormsby Prentice.
In 2007, the Lynch family joined Mr Conlan to buy a site on the outskirts of Waterford for €25m.
They intended to develop it into a big shopping centre with houses and apartments.
In the Commercial Court it was disclosed that Mr Lynch's former long-time friend and business associate Pascal Taggart warned him about getting involved in the deal.
"It sounds like a great deal," Mr Taggart said. "But if you play with Gerry Conlan long enough, you will lose because he is a gambler," the court heard.
Giving evidence, Mr Lynch later dismissed this description of Mr Conlan whom he knew well and had worked with as a director of his private hospital group.
He had invited the Lynch family into the Waterford deal as a "thank you" for his work, the court heard.
In evidence the family said Mr Conlan arranged all of the finance with the banks and that they believed he had secured a non-recourse loan, meaning that the bank could only take the site back if they couldn't repay the loan.
The bank denies this and is pursing the Lynch family and Mr Conlan for what is owed. They are awaiting a decision from Judge Michael Peart on the loan.
Mr Conlan's loans have now been transferred into NAMA which is working with him and his companies to recover as much money as it can for the taxpayer.