Before being sequestrated last month, Coakley was one of Scotland's more colourful businessmen. The property trader and developer flew a private jet, had a fondness for Rolls-Royces, and five years ago was at the centre of a failed bid to take over Motherwell Football Club.
He also pledged £1m over 10 years to the Scottish Conservatives in the run-up to the last election, only to withdraw the offer after the party chairman removed close associate Malcolm Macaskill from the top of the party's list of Glasgow MSPs for failing to disclose that he had twice been bankrupted.
In 2008, the Sunday Times Rich List estimated he had assets worth £70m, having dabbled in everything from business parks to the now-defunct Bar Budda chain, including ventures in London's Mayfair and Malaga.
But he was one of the entrepreneurs caught with too much debt when the market turned, and the past few months have seen his web of over a dozen companies mostly unwind.
The last major one still trading, St Vincent Street (491) Ltd (SVS), which controls a portfolio of over 50 properties around Scotland, was last week pushed into administration by Nationwide, which is owed £12.6m.
The company is owned by The Coakley Group, which has been in Coakley's wife Marlene's name for the past few years. It also owes £300,000 to Tennent Caledonian. This relates to a mortgage the brewer granted SVS over office space in Glasgow city centre.
SVS's administrator, London-based Moorfields Corporate Recovery, told the Sunday Herald a major financial institution is in talks with Nationwide to pay the debt and take over the firm.
Moorfields said The Coakley Group was in discussions with the institution before the administration but not quickly enough to prevent Nationwide from taking effective control.
One possible complication is a fund called Hadrian SARL, which was the main creditor to Coakley's other businesses. It is owed around £25m, a debt which it bought from collapsed bank Anglo Irish several years ago, presumably at a substantial discount.
In pursuit of this sum it sequestrated Coakley last month, having already pushed his family's other two main trading vehicles, Mar Retail and Regents Retail Investment Company, respectively into administration and liquidation last year.
It is based in Luxembourg, but its members include major Scottish players such as Edinburgh banker Ben Thomson.
According to official documents seen by the Sunday Herald, Hadrian believes it can only recover £1m from Mar, which owes the bulk of the debt but only owns three tracts of undeveloped land in Lanarkshire and Dundee.
But Hadrian may be able to recover up to £8m from SVS on the back of an agreement the company reached with Anglo Irish several years ago relating to property transfers by Mar and Regents to SVS that were used to pay down some of the total debt in 2010-11.
Hadrian has taken legal advice as to whether it would be able to recover this money from SVS, although the Sunday Herald could not ascertain at the time of writing whether it intended to raise an action. Moorfields was not aware of Hadrian's interest going into the weekend.
Mar also owed £2.7m to Coakley himself, an unsecured debt which Mar administrator PricewaterhouseCoopers did not think would be recovered. He also offloaded his Glenlora Estate at Lochwinnoch in Renfrewshire several years ago. It is currently valued on property site Zoopla at nearly £1.5m.
After his sequestration, Coakley resigned his directorship of nine companies in which his family has an interest, including Box Leisure, owner of The Box nightclub in central Glasgow. In the preceding months, he resigned as a director of The Coakley Group and Nico's, which owns a cafe bar of the same name in Glasgow.
In an interview in 2010, Coakley said that his businesses had "hit the bottom", and said that although he was not a reckless person "I will take chances", and described himself as a wild card.
He declined to give an interview last week, but stressed that he had not been an owner of The Coakley Group since 2007 and that that company had not gone into administration.
Hadrian could not be reached in time for publication.