Harold Tillman is in crisis talks to save the final piece of his retail empire.
Allders of Croydon, the department store in south London that Mr Tillman bought in 2005, is in crisis talks with its landlord to stave off administration.
It has requested a rent-free period and appealed to the local council for a business rates free period to give it breathing space.
Weak sales and a large rent bill have left the 300,000 sq ft store in dire straits.
In February, Mr Tillman restructured his ownership by reducing his stake to 35 per cent while retail restructuring expert Hilco took a 35 per cent stake and Royal Bank of Scotland's West Register took a 30 per cent equity slice.
But the restructuring may not be enough to save the historic store, which dates back to 1862.
Andrew MacKenzie, whom Mr Tillman appointed as Allders' chief executive, had been attempting to turn the business around by bringing in more concessions, but it is thought its rent bill each month is too large compared to its sales.
The situation in Croydon is the latest woe for Mr Tillman. His Jaeger retail business was sold to Better Capital in April for just above its level of debts, and Aquascutum was placed into administration later that month. But Mr Tillman retains a small stake in Jaeger.
Mr Tillman, who is the chairman of the British Fashion Council, bought Allders of Croydon out of administration in 2005, when it was part of a national chain of department stores.
The site of the store in Croydon is owned by Jupiter Properties, the joint venture between Delancey and Area Property Partners, who took control of the 500,000 sq ft building as part of its £202m purchase of the debt-laden property company Minerva in August last year.
The Allders site is of interest to the property developers Hammerson and Westfield who are in a battle to redevelop the centre of Croydon. Delancey hired a property agent to look at options of selling the site.
It is not the first time Mr Tillman has hit difficulties in retail. He was involved in the collapse of the Honorbilt fashion group in 1990, and was disqualified as a company director for three years.