From Sports Direct to…Hugo Boss? Why brash High Street tycoon Mike Ashley is poised to grab one of the world’s most prestigious fashion giants

It might seem that it is not often that the dignified entourage of London’s High Court hears talk of ‘vodka chasers’ and vomiting in pub fireplaces.

But in 2017 a judge at the commercial court heard the story of a memorable night at a drinking contest organized by Sports Direct founder Mike Ashley in a country pub, in which he downed a dozen pints and a few vodkas, then returned most of them back to the stove.

This unhealthy incident was brought up in one of the highest courts in the country because lawyers believed it showed how Ashley sometimes went about her business.

Banker Jeffrey Blue sued Ashley, claiming that she had reneged on her promise of a £15 million bonus during a night of excessive drinking at another bar, this time at The Horse and Groom in London.

It was claimed Ashley was no stranger to multi-litre business deals in the pub’s backrooms – but Blue lost his case after Mr Justice Leggatt found that although Ashley had made a verbal offer, it was merely a ‘joke’ and not legally binding.

Nine years later, it’s hard to imagine a corporate background less suited to the glitzy world of European fashion. Still, it looks like Ashley has her sights set on there.

Last week, it was revealed that Frasers Group, the retail empire managed by the 61-year-old billionaire, purchased German fashion giant Hugo Boss for 1.7 billion pounds.

Founded in 1924, the brand has built its reputation on stylish tailoring and first-class formal wear.

In other words, it’s a look miles away from the mass-market sneakers for which Ashley, a brash, old-school businessman, has made his name, not to mention the tracksuit bottoms he favors in his personal wardrobe.

No wonder eyebrows were raised last week over news of Ashley’s attempted takeover of Hugo Boss, which was, in the dry corporate language of the board, ‘unsolicited’ and ‘uncoordinated with the company’.

Even though it is not so, it must be said with surprise. ‘He has zero respect for norms of business conduct,’ a City expert told The Mail on Sunday, describing Ashley as ‘pure Marmite’.

The man is showing favoritism and has no time for niceties. Ruthless is his middle name. ‘He’s also brave and ready to put his money where his mouth is.’

The move appears typical of a man who has made a habit of subverting the conventions of corporate Britain to build one of the country’s biggest retail empires.

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

But if Ashley has spent her entire life subverting expectations, perhaps the first surprise is that she never set out to be a retailer.

Ashley, from Burnham, Berkshire, initially dreamed of becoming a squash player. A promising young man, his dreams were dashed due to injury at the age of 16. Having left his local grammar school without a single qualification, the teenager instead found himself helping out at a local sports shop.

He was just 18 when he took out a £10,000 family loan to open a sports shop in Maidenhead in 1982. Few could have imagined that the boy behind the counter would one day become one of the richest men in Britain, said to be worth £3.44bn, but the qualities that would define his career were already becoming evident.

One person who worked with him said, ‘When he looked at the figures, it was like he was watching Rain Man.’ ‘He could make out the numbers and immediately see where the problem needed to be fixed.’

He also had an appetite for risk: throughout the 1980s and 1990s Ashley expanded, opening stores in London and the South East, then rebranding the growing chain first as Sports Soccer, then Sports World (the company’s name when it listed on the stock exchange in 2007 for £3.3bn) and finally Sports Direct.

Meanwhile, rumors that she was living with one of the most powerful names in the industry helped determine Ashley’s reputation.

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

Unfortunately, if Whelan meant this as a warning, he appears to have misjudged his audience: in 2000 Ashley broke into the Office of Fair Trading to report football shirt price fixing, setting off a series of investigations that saw JJB fined £8 million.

David Beckham photographed modeling his first co-designed BOSS collection in 2025

The German fashion giant has been modeled and worn by many celebrities, including Kendall Jenner.

Although Whelan was not the last rival to discover that Ashley could be extraordinarily cruel, he never forgave her.

‘Most people in business are focused on doing their best, but Ashley is also focused on destroying the competition,’ the insider recalled. ‘This means war for him.’

While many have focused on widening the High Street over the years, Ashley has pursued a different strategy. He began buying brands whose best days were behind them (including Slazenger, Dunlop and Everlast). It made them more profitable by shifting production to cheaper locations.

As retailing evolved and many established chains stumbled, Ashley increasingly positioned himself as the man waiting on the sidelines when trouble arose. Today the Frasers Group includes 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 appeared random; Just like the belligerent Englishman’s idea of ​​​​taking over the understated brand Hugo Boss completely. In fact, Frasers has held a stake in Hugo Boss since 2020, when it acquired 5 per cent of the shares. And the move is part of what the company describes as an ‘ascension’ strategy for the brand.

Sports Direct was a decidedly lower-end chain until 2019, but in 2019 Ashley rebranded his empire as Frasers Group when he bought the struggling House of Fraser in a £90m deal.

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 £83 million takeover bid for luxury British bag maker Mulberry. Although he still held a 37 percent stake, he was rejected by the owners.

But as we have seen, despite Ashley’s obvious desire to buy more ‘prestigious’ brands, she remains almost willfully oblivious to conventional expectations of what a billionaire should look like.

While he’s acquired all the trappings of the wealthy (he owns a 33-room mansion in north London, complete with indoor and outdoor swimming pools and a cinema, as well as international properties), he prefers day-to-day leisure wear and gatherings in the back rooms of pubs.

In fact, former partners described meetings lasting into the early hours, fueled by kebabs, fish and chips, and endless rounds of beer.

Ashley described herself as an ‘energy drinker’ during a 2017 High Court hearing in which she was revealed to have vomited into a pub fireplace. “I like getting drunk,” he added.

His appetite for alcohol is matched by his fondness for gambling.

On one occasion in 2008, he bet £480,000 at the now-closed Fifty St James Casino in Mayfair, focusing on his lucky number 17, and walked away with a winnings of £1.3 million.

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

Ashley’s takeover of Hugo Boss was met with surprise as the board said it was ‘not coordinated with the company’

It’s a drop in the ocean compared to the losses it suffered during the financial crisis in 2008, when HBOS used high-risk spread betting and Contracts for Difference to speculate on its bank’s rapid recovery. The share price collapse resulted in a personal loss estimated at between £129 million and £300 million.

While he was set on purchasing Debenhams in 2019, he suffered a crushing defeat when the chain went into administration and his investment was wiped out. He is said to have lost £150 million.

Then came the £134 million purchase of Newcastle United football team in 2007, after which initial optimism from fans turned into criticism that the club was short of both good investment and managers.

He had become one of the club’s most unpopular owners when he sold the club to a Saudi consortium for £300 million in 2021.

They weren’t the only brickmakers in his career. In 2016, Ashley was summoned before the Parliamentary Select Committee after revelations about working practices at Sports Direct’s Shirebrook warehouse in Derbyshire revealed how poor conditions and wages were at the facility, which became known as a ‘gulag’.

A later report by a committee of MPs said practices were ‘closer to those of a Victorian workhouse than a modern, respectable High Street retailer’.

Ashley later admitted that the company had ‘outgrown’ his ability to manage him and launched a series of internal reviews to improve conditions.

It must also be said that the people at the Frasers’ headquarters were extremely loyal. ‘He’s a great boss,’ one employee told MoS. ‘No pretensions or graces, he’ll remember what’s going on with you in the pub and with your family.’

Ashley’s private life, meanwhile, has always been closely guarded: he married Swedish-born economics graduate Linda Jerlmyr in 1989, but the union ended in 2002, leading to what is widely believed to be one of the largest divorce settlements at the time.

Ashley has reportedly transferred numerous properties and assets worth a total of £50 million.

But in 2013, Linda was in a relationship with businessman Simon Brodin, with whom she now has a 20-year-old son, and the pair were spotted enjoying intimate dinners again.

They re-emerged publicly as a couple in 2016 when Linda accompanied Mike to a Parliamentary Select Committee to hear about working conditions in Sports Direct warehouses; this was a very public signal of support. It turns out they are still together.

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

And while son Ollie, 35, is a music promoter, in 2022 Ashley appointed the husband of her elder daughter Anna, 34, Michael Murray, then just 32, as CEO of Frasers; This was seen as one of the most brazen acts of nepotism in the city.

But as we see, Ashley doesn’t really care what people think.

As one City insider said: “He’s got obvious flaws, he gets in trouble with people, he plays to win and he’s not too worried if people get hurt.”

‘And with the High Street on its knees and Rachel Reeves crushing retailers with tax rises, you have to admire her courage.’