Liam Carroll

In the space of two years, developer Liam Carroll has gone from being a cash billionaire to struggling to pay his creditors. Last week, Irish Nationwide was in court claiming it is owed €60m through a personal guarantee but Carroll says the real figure is €30m. It was all far removed from the idyllic days of 2007 when Carroll securitised income from many of his properties via a deal with Bank of Scotland (Ireland) allegedly giving him about €800m in cash.

Last week the High Court heard that Carroll's assets total €259.5m, his bank debt stands at €149m and that he receives annual rental income of €9.85m while paying annual interest of €7.9m. The Irish Nationwide case arose from a €66.5m loan to Aifca, one of the defendants in a legal action taken by developer Noel Smyth against Carroll and others, seeking damages of €150m.

For a man as wealthy as Carroll was, those figures, though eye-opening, should have been bearable. So what went wrong? It seems that Carroll could not have chosen a worse time to move into the stock markets, as he sought to diversify away from property. After receiving the securitised income he went on a share-buying spree, investing in everything from sugar to ferries. Millions were invested in Greencore, Irish Continental Group, McInerney and Aer Lingus, stocks that had little in common other than the fact that they had land banks, and land was what Carroll understood.

But the stock markets plummeted after his investment and, as revealed in the Sunday Tribune, his Bloomburg vehicle alone lost €75m in two years in the stock market. Another company, South Morston Investments, lost nearly €58m on investments in Irish Continental Group. The most serious losses were at a third company, Gainsco – its listed investments costing more than €200m were valued at less than €77m in January of this year.

It's a long way from Carroll's early forays into the stock market, when he bought Dunloe Ewart for a steal and became involved in the battle for control of Jurys Doyle, although he came to that party too late to profit as much as rival developer Seán Dunne did from his share acquisitions. The Doyle family, though, were the real winners, essentially walking away with the Jurys hotels for free after offloading some of the group's other interests.

Carroll was already wealthy by then of course, having profited hugely from the urban renewal tax breaks under which he offloaded thousands of apartments, particularly around Dublin 7 and Dublin 8, before moving into commercial development. The deaths of three workers on his sites brought unwelcome attention though, and he was described as a "recidivist" criminal in court.

He didn't get caught up in the "my helicopter is bigger than yours" melodrama that characterised property developers's lifestyles. Carroll is a family man whose focus has always been one of his daughters in particular, as well as wife Róisín and his other children. Private jets, PR men, Armani suits and luxury cars were not his way. Property was in effect a hobby as well as a job; estate agents speak of him turning up for house viewings around the Dublin area on his days off.

Naturally, there were occasional noticeable signs of wealth but nothing garish. Mobile home holidays in Mornington turned into trips to a villa in Portugal; the Toyota Corolla became an Avensis with a Mercedes S Class for the weekend; and the woolly jumper and jeans would occasionally be swapped for a suit, shirt and tie – only occasionally, mind you.

Carroll's empire sprawled so far that people began to wonder how he could keep track of all of it. Planning permission for a huge development at Sir John Rogerson's Quay in Dublin was refused extra time to complete because insufficient works had been carried out, and he was also forced to seek an extension of time for two sites in north Dublin.

His decision to pull the sale of the apartments in the former gasometer in Dublin 4 backfired when residential property prices continued to drop. The Dublin Airport Authority, his joint venture partner, is believed to have been unaware that he offered a site they jointly own at Harristown in north Dublin to Bohemians Football Club for a new stadium as part of a deal to take over Dalymount Park. He also pulled workers off The Parkway Valley shopping centre in Limerick.

In Dublin, he is awaiting a decision from An Bord Pleanála on whether he can retain and complete the skeleton structure that is to house Anglo Irish Bank's new headquarters, and he has stepped up the construction timetable for State Street's new headquarters at Dublin's south docks.

He was once the biggest speculative developer in the country, regularly constructing buildings with no tenant in place. When the building was complete he would undercut rival developers ruthlessly, often offering rents at 50% below the market rate. He believed he would get the money back after the five-yearly upward-only rent reviews that are standard in this country.

Since the downturn, though, numerous legal actions have been taken against Carroll's companies. Ten High Court actions have been launched against Danninger alone since the start of the year. Last month Deepdrill Developments, a joint venture between the O'Dwyer pub group and Bennett Construction, sought to have Danninger wound up. It followed a 2007 court case relating to a site at Abbey Street, details of which show just how informed Carroll was about the Dublin property market. According to Judge Charleton's 2007 judgement, Carroll rang Liam O'Dwyer saying he was going to lose out in the best bids process to Deepdrill, before Deepdrill was even aware it had won the tender.

Talk of his financial difficulties have been circulating since the third quarter of last year. He later began to offer creditors 60 cent in the euro. It is rumoured one of the banks has given him an office in its headquarters because he spends so much time there.

People who know Carroll say he was in good spirits last week, despite the court case. There is a general feeling that, even if Irish Nationwide wins its action, AIB and BoSI will give him more money to pay his debts, as they did earlier this year. For the banks, Nama is simply too important for anything or anyone to be allowed to derail it.