Philip Green was a rough-around-the-edges entrepreneur knighted for services to retail before scandals, a bankruptcy and claims of tax avoidance tarnished his image.
The so-called "king of the high street" stormed into the limelight in the early 2000s when he bought some of Britain's best-known department stores and chains.
He also cultivated numerous celebrity friends, including model Kate Moss and Vogue editor Anna Wintour, relocated to Monaco and spent much of his life on a 300-foot super-yacht.
Two decades on, his retail group Arcadia faces financial ruin after years of underinvestment and failure to recognise the shift to online shopping.
Along the way Mr Green has faced calls to be stripped of his knighthood after the once-flagship chain BHS went bankrupt with a huge pensions fund shortfall.
Greed comes before a fall
The tycoon paid himself £1.2 billion ($1.6 billion) in tax-free dividends in 2005 - more than four times the company's pre-tax profit.
His residency in tax haven Monaco was criticised, and the 68-year-old was caught up in the global #MeToo movement, accused of sexually harassing and racially abusing staff.
But it is his failure to adapt to changing consumer trends that looks to have prompted his ultimate downfall.
The Sunday Times described him as the "consummate analogue man in a digital world", citing his dislike for modern tech culture as central to his empire's imminent demise.
"In the end, even this fiercest of retail dinosaurs has been ripped apart by more sophisticated predators," the newspaper said this weekend.
Who is Sir Philip Green and what businesses does he own?
Mr Green was born in south London in 1952 into a wealthy Jewish family which had made its money from petrol stations.
He studied at the now-defunct private school Carmel College -- known as "the Jewish Eton" -- but quit aged 16 without completing the usual graduating exams.
He started his career buying bulk designer clothing stock and reselling in the upmarket London neighbourhood Mayfair, before becoming chief executive and chairman of discount retailer Amber Day.
Mr Green left the listed company after it missed a profit forecast, re-emerging in the late 1990s to bid for the remains of the Sears empire, a separate entity to the US enterprise.
He then acquired a string of other high street brands, including BHS in 2000 and Arcadia in 2002.
In May 2004, however, Green perhaps met his match when he launched a £9.1-billion takeover bid for clothes-to-food retailer Marks and Spencer.
He was outmanoeuvred after M&S recruited former Arcadia boss Stuart Rose to become chief executive and successfully fended off the audacious offer.
But the tycoon initially turned around the loss-making BHS, gaining plaudits in the process and the title "Sir" Philip Green in 2006.
Former Prime Minister Tony Blair, whose government selected Mr Green for the knighthood, described him as "the person who thought up the dream and dreamt the dream into reality".
The beginnings of the end
The 2008 global recession marked the start of a more nightmarish period.
BHS, once a behemoth of British retail, began to haemorrhage money and see its pension deficit balloon.
At the same time, fashion upstarts such as Asos and Boohoo ate into his core businesses.
Green delayed selling BHS until 2015. The only buyer was Dominic Chappell, a serial bankrupt who paid a token £1 and ran it into the ground.
The closure cost 11,000 people their jobs and left a £571-million hole in the pensions fund.
Facing lawmakers' unprecedented moves to revoke his knighthood, Green eventually agreed to hand over £363 million for the pensioners.
In 2018, The Daily Telegraph reported that staff bound by non-disclosure agreements were accusing an unnamed businessman of sexual harassment and racial abuse.
Mr Green was soon identified as the accused by a lawmaker in the House of Commons using parliamentary privilege. He categorically denied the allegations.
Two female employees reportedly received hundreds of thousands of pounds in compensation after his lawyers admitted he had acted in a "tactile" way and "prodded and poked individuals".
What is Philip Green's net worth?
Arcadia's severe woes do not appear to have dented Green's immediate finances - he has amassed an estimated fortune of $2.3 billion, according to Forbes.
Continuing a trend for lavish birthday parties on luxury islands, The Guardian said Green is booked into the One & Only Reethi Rah resort in the Maldives this Christmas.
Private villas costs up to £30,000-a-night and guests arrive by seaplane.
The broader outlook for Green is far less rosy.
"He's gone from zero to hero, and now it looks like he's going back to zero again," retail analyst Richard Hyman told the newspaper.