One imagines it is not often that the dignified environs of London’s High Court are subject to talk of ‘vodka chasers’ and vomiting in pub fireplaces.

In 2017, however, a judge in its commercial court heard the tale of a memorable evening during which a drinking contest in a country pub, organised by Sports Direct founder Mike Ashley, had ended with him downing a dozen pints and several vodkas... then bringing most of it back up again in the hearth.

This insalubrious episode was raised in one of the highest courts in the land because lawyers believed it demonstrated how Ashley sometimes conducted his business.

He’d been taken to court by banker Jeffrey Blue, who claimed Ashley had reneged on a £15million bonus promise made during a night of heavy drinking in another pub, this time a London hostelry called The Horse and Groom.

Ashley, it was suggested, was no stranger to business dealings in pub back rooms over several pints – although Blue still lost his case after Mr Justice Leggatt determined that while Ashley may have made a verbal offer, it was merely ‘banter’ and not legally binding.

Nine years on, it is difficult to imagine a corporate back story less suited to the polished world of European fashion. And yet it is precisely there that Ashley now appears to have set his sights.

Last week it emerged Frasers Group, the retail empire overseen by the 61-year-old billionaire has mounted a £1.7billion takeover of the German fashion giant Hugo Boss. 

Founded in 1924, the brand has built its reputation on sleek tailoring and premium formal wear.

In other words, an image miles away from the mass-market trainers with which Ashley – a brash, larger-than-life old-school tycoon – made his name, not to mention the tracksuit bottoms he favours for his personal wardrobe.

Little wonder that news of Ashley’s attempted takeover – ‘unsolicited’ and ‘not coordinated with the company’ in the dryly corporate language of Hugo Boss’s management board last week – has met with raised eyebrows.

Although not, it must be said, with surprise. ‘He has zero respect for the norms of business behaviour,’ one City expert told The Mail on Sunday, describing Ashley as ‘pure Marmite’.

‘He has been nepotistic and has no time for niceties. Ruthless is his middle name. At the same time, he is bold and prepared to put his money where his mouth is.’

The move seems typical of a man who has made a habit of crashing through the conventions of corporate Britain to build up one of the country’s largest retail empires.

Frasers Group employs more than 30,000 staff, has 1,500 stores in 20 countries and its most recent accounts showed net assets of around £2.4 billion.

Yet if Ashley has spent a lifetime confounding expectations, perhaps the first surprise is that he never set out to be a retailer at all.

Ashley, who hails from Burnham, Berkshire, initially dreamed of becoming a squash player. A promising junior, his dreams were curtailed by injury aged 16. The teen who had left his local grammar school with not a single qualification, instead found himself helping out in a local sports shop.

He was just 18 when he used a £10,000 family loan to open a sports store in Maidenhead in 1982. Few would have imagined that the boy behind the counter would one day become one of Britain’s richest men, said to be worth £3.44billion, yet the qualities that would define his career were already becoming apparent.

‘When he looked at numbers, it was like watching Rain Man,’ one person who worked with him said. ‘He could pick figures out and immediately see where an issue needed fixing.’

He also possessed an appetite for risk: throughout the 1980s and 90s, Ashley expanded, opening stores across London and the South East before rebranding the growing chain as first Sports Soccer, then Sports World (its name when the company floated on the stock exchange for £3.3 billion in 2007) and finally Sports Direct.

Along the way a rumoured confrontation with one of the industry’s most powerful figures helped define Ashley’s reputation.

According to industry folklore, Dave Whelan, founder of JJB Sports, once warned Ashley that he was entering territory dominated by established northern operators. ‘There’s a club in the North, son, and you’re not part of it,’ he is reputed to have said.

Alas, if Whelan intended it as a warning, he appears to have misjudged his audience: in 2000 Ashley walked into the Office of Fair Trading to whistleblow on football shirt price fixing, setting in train a series of investigations that saw JJB slapped with an £8million fine.

Whelan never forgave him, although he was not the last rival to discover that Ashley could be extraordinarily ruthless.

‘Most people in business focus on operating the best they can but Ashley also focuses on destroying the competition,’ one insider recalled. ‘It is war to him.’

For years, while most focused on High Street expansion, Ashley pursued a different strategy. He started acquiring brands (among them Slazenger, Dunlop and Everlast) whose best days appeared behind them. He made them more profitable by shifting manufacturing to cheaper destinations.

As retailing evolved and many established chains stumbled, Ashley increasingly positioned himself as the man waiting in the wings when trouble struck. Today Frasers Group spans everything from Sports Direct and House of Fraser to Evans Cycles and Missguided, as well as stakes in retail giants ASOS and Currys.

To many observers, his strategy has looked random – as, at face value, has the thought of the pugnacious Brit taking on understated brand Hugo Boss in its entirety. In fact, Frasers has held a stake in Hugo Boss since 2020 when it bought 5 per cent of the shares. And the move is part of what the company describes as an ‘elevation’ strategy for the brand.

Until 2019, Sports Direct was a decidedly downmarket chain but, when in 2019 Ashley bought the struggling House of Fraser, in a £90million deal, he rebranded his empire as Frasers Group.

It now owns premium brands including Jack Wills, designer retailer Flannels and luxury tailor Gieves & Hawkes.

Two years ago, Ashley tried to move even further up the fashion chain with an £83million takeover bid for luxury British handbag maker Mulberry. He was rebuffed by the owners, although he still owns a 37 per cent stake.

Yet as we have seen, despite Ashley’s apparent desire to take on more ‘prestige’ brands, he remains almost wilfully indifferent to conventional expectations of what a billionaire should look like.

While he may have acquired all the trappings of the wealthy – there is the 33-room mansion in north London complete with indoor and outdoor swimming pools and cinema, alongside international properties – day to day he favours leisure wear and meetings conducted in pub back rooms.

Indeed, former associates have described meetings stretching into the early hours over endless rounds of beer, fuelled by kebabs and fish and chips.

In the 2017 High Court hearing in which it emerged he had vomited into a pub fireplace, Ashley described himself as a ‘power drinker’. ‘I like to get drunk,’ he added.

His appetite for alcohol has been matched by his predilection for gambling.

In one 2008 incident he made bets to the tune of £480,000 all centring on his lucky number, 17, at the now defunct Fifty St James Casino in Mayfair, walking away with a £1.3 million win.

While on another occasion he settled a £750,000 legal fees dispute during a City meeting by playing a round of the pub gambling game ‘Spoof’, in which players guess how many coins are held in total in the clenched fists of the group. He lost and paid the bill.

A drop in the ocean compared with his losses in 2008 when, during the financial crisis, he used high-risk spread bets and Contracts for Difference to speculate on a rapid recovery for the bank HBOS. When its share price plummeted, it resulted in a personal loss estimated between £129million and £300million.

In 2019, having set his heart on acquiring Debenhams, he also suffered a crushing defeat when the chain crashed into administration, wiping out his investment. He is reported to have lost £150million.

Then there’s his £134million buyout of football team Newcastle United in 2007, following which the initial optimism of fans was replaced with criticism that he was starving the club of both decent investment and managers.

By the time he sold the club to a Saudi consortium in 2021 for £300 million, he had become one of its most unpopular owners.

They have not been the only the brickbats in his career. In 2016, Ashley was summoned in front of a Parliamentary Select Committee following revelations about working practices at Sports Direct’s Shirebrook warehouse in Derbyshire, which exposed how conditions and pay were so poor the facility was known as ‘the gulag’.

A subsequent report by a committee of MPs said the practices were ‘closer to that of a Victorian workhouse than that of a modern, reputable High Street retailer’.

Ashley subsequently admitted that the company had ‘outgrown’ his ability to manage it, and initiated a series of internal reviews to improve conditions.

It must be said, too, that those at Frasers’ HQ are fiercely loyal. ‘He’s a brilliant boss’ one employee told the MoS. ‘There’s no airs and graces, he’s at the pub with you and he’ll remember what’s going on with your family.’

Ashley’s own private life, meanwhile, has always remained closely guarded: in 1989 he married Swedish-born economics graduate Linda Jerlmyr, but the union ended in 2002 prompting what was widely believed to have been one of the biggest divorce settlements of the time.

Ashley reportedly handed over multiple properties and assets with a total worth of £50million.

Yet in 2013, by which time Linda had had a relationship with businessman Simon Brodin, with whom she had a now 20-year-old son, the pair were spotted together again enjoying intimate dinners.

In 2016, they publicly re-emerged as a couple when Linda accompanied Mike to the Parliamentary Select Committee hearing into the working conditions at his Sports Direct warehouses, a highly public signal of support. It is understood they are still together.

The couple have three children. Matilda, 29, is a director of Mash Holdings, which controls her father’s stake in Frasers Group and other companies.

And while son Ollie, 35, is a music promoter, in 2022, Ashley appointed the husband of elder daughter Anna, 34, Michael Murray, then aged just 32, as CEO of Frasers, an appointment seen as one of the City’s most brazenly nepotistic.

But then, as we’ve seen, Ashley doesn’t much care about what people think.

‘He has obvious flaws, he falls out with people, he plays to win and if people get hurt he is not particularly worried,’ as one City insider said.

‘And with the High Street on its knees and Rachel Reeves hammering retailers with her tax hikes, you have to admire his guts.’