Green was the chairman and chief executive of Amber Day from 1988 to 1992. In 1999, he acquired Sears plc. He bought British Home Stores (BHS) for £200 million in 2000, and subsequently spent £840 million to acquire the Arcadia Group in 2002. Arcadia became a private company and was delisted from the London Stock Exchange. He unsuccessfully sought to acquire Marks & Spencer in 1999 and 2004.
Green was made a Knight Bachelor in the 2006 Birthday Honours. He has been called the "King of the High Street" but has been involved in a number of controversies during his career, including his actions prior to the demise of BHS in 2016.