He made his first million by cleverly buying, turning around and finally selling a failing retailer called "Jean Jeanie". Buying the company for £65,000 plus debt, which he negotiated a goodwill gesture of £100,000 with the main lending bank to freeze repayments with as he tried to turn the business around, he ended up selling for £9 million of which he paid off its debt and walked away with £6 million. These early examples of entrepreneurship and clothes retailing expertise were to foreshadow his later bigger successes.
In the early 1990s Green bought the department store chain Owen Owen which at the time had about 12 branches trading under the Owen Owen and Lewis's brand names. During his ownership most of these department stores were sold to other operators including Debenhams and Allders or were closed leaving only the Liverpool branch trading as Lewis's remaining. In 2004 this remaining store was sold off to David Thompson.
In 1995 he linked with Tom Hunter to buy sports retailler OLYMPUS, as part of a merger. The price was one British pound, plus the assumption of £30 million in debt. Green and his partners sold the company three years later to JJB Sports for £550 million. Green walked away £73 million richer. That encouraged the Barclay brothers to back him in the £538m acquisition of the Sears retail chain (a different Sears from Sears, Roebuck and Company) in 1999. The subsequent disposal programme (including selling some of the assets, ironically, to Arcadia) raised £729m and confirmed his reputation as a man who could deliver within the retail sector.
Green came to public attention in 1999 when he attempted to make a £7 billion hostile bid for Marks and Spencer. However the leaking of the bid forced up M&S's share price. The board of M&S were also hostile to the bid and sought to block it. Eventually Green gave up and purchased the ailing retail chain BHS for £200 million. His takeover came when everyone else had dismissed the company as a failing brand and unfixable. Green put up £50 million of his own money and borrowed another £150 million to seal the deal. Green completely turned the company around, rebranded it as BHS, and the chain is now thought to be worth over £1.2 billion. Since he took over, profits have tripled to over £200 million a year.
Next, Green purchased the Arcadia Group, which owns well-known High Street chains such as Burton, Dorothy Perkins, Evans, Miss Selfridge, Outfit, Topshop/Topman and Wallis in 2002. Recently he has added the Etam chain to the group. Green paid £850m, and repaid the £808m he borrowed to finance the deal in two years, a move that stunned commentators when it was announced. The Arcadia Group has been enormously profitable, and currently has pre-tax profits of around £380 million.
On 20 October 2005 Green awarded Arcadia shareholders a £1.3 billion dividend. He and his wife are joint owners of 92% of the group, and therefore received £1.17bn - the largest payout to an individual in British corporate history.