Philip Green is no stranger to laying the odd wager, but his latest punt for Marks & Spencer (M&S) could be the British billionaire's boldest gambit yet.
Mr Green, whose empire ranges from the Bhs department stores to the Top Shop and the Dorothy Perkins fashion chains, is preparing what could turn out to be a £9 billion bid for Britain's top clothing retailer.
It is still early days, but this is not the first time that Mr Green has eyed the 100-year-old doyen of Britain's high streets and one of its most venerable names.
Mr Green, who abandoned a plan to bid for the company in 2000, could be one of Marks & Spencer's better suitors, given his self-belief and his reputation as died-in-the-wool retailer and turnaround artist.
These are qualities that M&S, which has been losing market share to clothing rivals such as Next and supermarkets such as Wal-Mart's ASDA, will sorely need.
Mr Green crafted one of the most successful retail recoveries in the UK, when Bhs, the department store chain he acquired in 2000 for £200 million, was transformed from a dud into a star in under two years.
M&S, which has been fighting to win back the affections of shoppers for over three years under chairman Luc Vandevelde, may need such a Midas touch. Mr Vandevelde is now on his way out, and the market seems to have lost confidence in Chief Executive Roger Holmes as the recovery flags.
Mr Green said yesterday that, if successful, he would personally run M&S's non-food and clothing businesses, and most analysts would certainly welcome that.
Starting off selling shoes some 36 years ago, Mr Green's ascent to the No. four position in the Sunday Times' 2004 rich list, with a personal fortune of around £3.6 billion, is the stuff of storybooks.
Mr Green, who never went to business school - in fact, the story goes that he left formal education at age 15 - is known for his keen business sense, with an eye for detail that sees him make decisions on the purchase of plastic bags to coat hangers.
Labelled variously as flashy, abrasive and tenacious, he is rumoured to be willing to gamble a million or two over the course of an evening.
His deal-making skills are renowned in London's financial district, where many are wary of his feisty temper. "You don't want to disagree with Philip," said one source who has worked with him in the past.
There is largesse too. At his 50th birthday party two years ago, some 250 guests received invitations in a crocodile-skin wallet to board an aeroplane to an unknown destination - which turned out to be Cyprus. The event was reported to have cost £5,000,000.
But alongside lavish gestures such as this, Mr Green also holds a regular Christmas bash in the more modest surroundings of the Bhs Oxford Street store, where B-list celebrities and investment bankers share mince pies and mulled wine between racks of women's clothes and Christmas trinkets.
Mr Green, who spends his weekdays in a London hotel before flying off to Monaco at the weekends to join his wife and their two children, said he hoped to make a proposal to M&S sometime next week, adding: "I have finance virtually in place."
One banker, who asked not to be named, said he did not think Mr Green would risk any of own money. "You can bet he's not going to get any poorer out of this. He'll make sure the public shareholders and banks pay for it," he said.