Now it would appear that the empire of tax exile Paul Green, the retail tycoon behind the £350m Silverburn shopping centre and other major Clydeside retail parks, is also starting to crumble after it emerged that five companies connected to the businessman have fallen into administration.

The elusive entrepreneur, who is based in Jersey, was thrust into the spotlight in 2007 after it was found that a £950 personal donation to Wendy Alexander’s leadership campaign broke the strict rules governing party finance.

While he was never found guilty of any wrongdoing, the episode led to the resignation of Ms Alexander as party leader after she was found to have broken Holyrood rules on the disclosure of donations.

The episode also led to Charlie Gordon resigning as party transport spokesman.

It was Mr Gordon who arranged the cheque from Mr Green, whom he knew well. Planning permission for the landmark Silverburn shopping centre was granted during Mr Gordon’s reign as leader of Glasgow City Council.

For the past two decades Mr Green has focused much of his energies on developing retail in the city.

He took bits of land that nobody wanted, remnant’s of the city’s painful industrial decline, and turned them into places of aspiration, such as the Parkhead Forge and the old Goodyear tyre factory in Drumchapel, which was transformed into the Great Western retail park.

In 2007, the Silverburn complex in Pollok, Scotland’s biggest shopping centre, was opened. Mr Green liked the scheme so much that he named a beloved racehorse after it. Silverburn, the gelding, has netted him at least £45,000 in prize money.

But it would appear that the good life is starting to sour after it emerged that five companies within the Green portfolio – Elementary Property Company, Premier Markets, Elementary Holding Company, Thorotat and Quest Investments – were all put into either administration or receivership, or both, on July 19.

Under a complex structure of company subsidiaries, Silverburn, which only last month announced plans to invest £20m in the third and final phase of its expansion programme, is owned by Guernsey-based Retail Property Holdings, an entity that had been ultimately controlled by the Jersey tycoon.

Sources told The Herald that Elementary Holding Company is the parent of Retail Property Holdings – though this could not be immediately confirmed because the firms were registered on the Channel Islands.

Administrators Deloitte last night said the five companies “have a number of assets, principally land and property in Glasgow and the surrounding areas”.

A Deloitte spokesman added: “Retail Property Holdings and Silverburn itself remain outwith the insolvency process.”

The spokesman also confirmed that Lloyds Banking Group, the owner of Bank of Scotland, acted as the primary financier to the companies, having funded a large part of the Silverburn development, and therefore now also a major creditor.

It was unclear if either of the Great Western retail park or the Forge at Parkhead could be affected, or if the trouble at Elementary would have an impact on the expansion at Silverburn. A planning application for the 75-acre site, off Junction 2 on the M77, is imminent.

One large “anchor” unit and 10 smaller shops are to be added to the retail complex, expanding Scotland’s largest purpose-built regional shopping development to 115 shops covering almost 1.1 million square metres.

Mr Green was listed this year in the Sunday Times Rich List, whose criterion includes business interests north of the border, as the 66th richest man in Scotland with a personal fortune estimated at around £60m.

Despite his commitment to Glasgow, Mr Green has no obvious links to the city. Born in Northampton and brought up in Bletchley, he has commanded his business from his base in the Channel Islands, where he lives with his wife and children.

He retired to the island in 1984 after selling a portfolio of property and floating a law stationery firm on the stock exchange, but he was soon in business again.

“I was only retired for a month then I got bored and my wife got fed up with me, so I started all over again,” he said at the time.

When asked what drew him back to Glasgow, Mr Green simply said: “I specialised in Glasgow because I happen to like the people. They are good people who tend to look on the bright side of life.”

Whether Mr Green still feels so optimistic is yet to be established. The Herald was unable to contact him last night.