“It’s like he’s playing Pokémon or something – trying to catch ‘em all.”

As far as comparisons go, it’s arguably one of the more flattering that Mike Ashley has received during his colourful career. And as he adds Game Digital to his growing stable of high street brands, few could disagree with that analogy, coined by a source close to his Sports Direct empire.

mike ashley

Since buying Newcastle United, Ashley has become one of the most recognisable business faces in the country

Ashley’s seemingly scattergun approach to snapping up retail names has already helped him acquire the likes of House of Fraser, Evans Cycles, Sofa.com, Agent Provocateur, USC and Flannels. Add to that sizable stakes in Findel and French Connection, and there are surely few people in UK retail with more power than Ashley.

It is a far cry from his humble beginnings when in 1982 – still in his late teens – Ashley launched his first store in Maidenhead, trading under the fascia of Mike Ashley Sports. By the time he turned 20, a second store was open for business in Golders Green.

His reputation as a market trader with a keen eye for deals and detail, coupled with a competitive streak sharpened during his time playing squash for Hertfordshire, formed the foundations upon which to build a retail powerhouse

But for a man who has grown one of Britain’s biggest businesses from the ground up, initially using a £10,000 loan from his parents, Ashley remains an enigma, a maverick and as unpredictable as he is entrepreneurial.

Ashley was a very private man and before Sports Direct floated few could pick his face out of a line-up. However, just two months after he took his business public in March 2007, he made one of the most high-profile moves a businessman could do – bid for a Premier League football club.

Now he is one of the most recognisable business people in Britain.

Despite his high profile, Ashley remains a mystery. Few really understand what makes him tick, what the grand plan is for his £1.2bn group or the financial implications his acquisitions could have, following the postponement of Sports Direct’s full-year results last week.

The mafia-like inner circle

Only those in Ashley’s “inner circle”, a “mafia-like family” of around a dozen people who he trusts implicitly, will truly know the answers.

Sports Direct’s head of elevation – and Ashley’s future son-in-law – Michael Murray, head of strategic investments Liam Rowley and his “fixer” when it comes to deals, Justin Barnes, all count themselves among Ashley’s “brothers” in that family, alongside his actual brother John, who was controversially paid £11m for building the retailer’s IT systems.

Game soho arena

Game Digital is the latest addition to the Sports Direct empire

CBRE’s Malcolm Dalgleish is one of few people outside of the small Sports Direct management team to have Ashley’s ear, having advised on his property portfolio since the early 2000s. Lee Charnley, the man he appointed managing director of Newcastle United, is another.

But in recent years, Ashley has lost a number of other trusted lieutenants. Karen Byers abruptly left the business at the start of this month after 28 years of loyal service, leaving a void in that close-knit group. Former Sports Direct boss Dave Forsey and chair Keith Hellawell have also stepped down in the past three years.

Those who have earned the privilege of a place at Ashley’s top table have done so not by being yes men. He surrounds himself with straight-talkers who are not afraid to challenge his school of thought.

“Mike doesn’t trust people until, in his view, they have earned the right to be trusted,” one source says. “They have to be incredibly loyal, honest, straight-talking, be on board with the vision and work tirelessly to make that happen. If you do that, you’ll be all right by Mike.”

Being “all right by Mike” has proved lucrative in the past, with Ashley happily rewarding the loyalty and hard work of his senior leaders.

When Sports Direct floated back in 2007, Forsey, Byers and Barnes were among a clutch of directors who took home bonuses worth £5m apiece.

However, even among those who have worked their way into Ashley’s “family”, there is little room for sentiment. Breach his trust or fail to toe the line and you can very quickly become a bête noire, as former Merrill Lynch investment banker Jeffrey Blue found out.

Blue helped float Sports Direct in 2007 before being employed directly by Ashley to drive “strategic opportunities”. However, the pair fell out – and Blue threatened to sue Ashley – when the tycoon failed to come good on a promise allegedly made in the pub to pay Blue an eight-figure bonus if Sports Direct’s share price doubled to £8, a target it hit in August 2015.

Ashley is said to have offered Blue £1m to “go away” and avoid the hassle of a court case, but the former banker is alleged to have threatened to tell all about Ashley’s boozy escapades in a bid to scare him into paying more. Ashley refused point-blank, effectively challenging Blue to do his worst. Stories of Ashley’s lurid drinking sessions and vomiting in pub fireplaces were thrust into the public eye during the court case – which Ashley eventually won – but he refused, as he so often does, to blink first.

hmv sign

Ashley lost in the race to buy struggling music chain HMV

“Mike knew the sort of stories that were likely to come out, but he wasn’t fazed,” says one insider. “That’s Mike at his best – he really doesn’t care.

“If you cross Mike in that way it’s very difficult to regain that trust. There are a lot of other people, like Sir Philip Green, who were fairly close to him but are now persona non grata. Anyone who f**ks up gets that treatment – and in Mike’s world, it’s not that difficult to f**k up.”

Green and Ashley were once good friends. The sportswear magnate even referred to Green as ‘The Emp’, short for the emperor, while the Arcadia tycoon, in turn, called Ashley ‘Little Emp’.

It is thought the pair have started to paper over the cracks in their fractured friendship, but Ashley is unlikely to ever fully forgive Green for thwarting his attempts to snap up HMV.

Green is understood to have been controlling the sale of the music chain behind the scenes, advising the then-HMV owner, Hilco executive chair Paul McGowan.

One person close to that deal says: “Philip said he would give Mike the last call to give him a chance to beat whatever had been offered by other bidders. But he never called him – and Mike’s not really forgiven him for that.

“Mike always gets a call whenever there’s a retailer on the block. He almost lost out on House of Fraser to [Edinburgh Woollen Mill owner] Philip Day – he’d pretty much pulled out and given up until he got a very late call. But the one he was really annoyed about was HMV – he really wanted that.”

Ashley’s evolving masterplan

HMV would have made Ashley’s eclectic portfolio of retail businesses even more diverse.

It has long been asked what Ashley’s grand plan is for his various acquisitions, which span lingerie, furniture and bicycles, and there is a suggestion even he doesn’t know how to knit them together. But Ashley simply cannot turn down a bargain – or a gamble.

A keen punter known to blow thousands on nights out at casinos such as Mayfair’s Fifty – a regular haunt of Ashley’s prior to its closure – the entrepreneur has taken that mentality into his business.

house of fraser glasgow

Ashley had long coveted a department store before buying House of Fraser in 2018

“You could imagine someone like Philip [Green] saying to Mike: ‘What are you doing?’ Sometimes I don’t think even Mike knows himself,” one ally admits.

But Dalgleish says: “Mike is of the mentality that you can try 10 things and as long as two or three work that’s OK. Mike looks at the marketplace at the moment and sees good deals. A lot of the brands and retailers he’s got now have been bought really cheaply.”

Some of his acquisitions may be spontaneous, opportunistic bargain buys, but Ashley had long yearned to get his hands on a department store and, having succeeded with House of Fraser where he failed with HMV, that business has become Ashley’s pet project.

He has entrusted protégé Murray to revamp Sports Direct to such an extent that Ashley is understood not to have his own office in the retailer’s Poland Street base – the new strategic hub for the group – so that he can focus on rejuvenating House of Fraser, a chain he aims to transform into “the Harrods of the high street”.

HMV, especially its stock of vinyl, Blu-ray discs and themed T-shirts, mugs and toys, had been a central part of a vision that one property source likens to “a department store for dudes”.

Ashley’s new-look House of Fraser sites, some of which will be rebranded to luxury chain Frasers, will focus more keenly on menswear and experiential grooming services such as in-store barbershops. 

Athleisure, a trend House of Fraser was slow to lean in to, will be given increased prominence and Ashley is mulling introducing aisles of running shoes and gym equipment. Sofa.com concessions are being introduced to enhance the homewares offer and Ashley wants Game’s Belong gaming arenas in stores.

Meanwhile, he is looking to bring celebrity chefs and upmarket eateries into Frasers.

The billionaire has received much criticism for the way he has handled House of Fraser so far, engaging in heavy discounting and adding his own brands like Kangol, Lonsdale, SoulCal and Everlast to the proposition. Commentators argue this has hindered its bid to go upmarket.

Yet Dalgleish, who was previously a Sports Direct non-executive, says: “Give it time. Mike had a plan before he bought the business, but that plan has changed. Retail is moving quickly and so that plan has had to evolve. There’s a lot of potential there – I think we’ll see things start to happen in the next 12 months.”

The business mechanic

The billionaire may have more up his sleeve, but questions remain over whether Ashley has the strategic nous and balance sheet to make his vision a reality – particularly after the shelving of Sports Direct’s full-year results.

But one of his former colleagues says: “When he applies himself to the detail of operational works, how things should be done and what should be traded in, he is a genius.

Flannels silverburn menswear

Flannels gives Ashley access to selling premium brands

“He didn’t want to be in the pit lane of Formula One, taking all the glory. He can see through the silos of finance, marketing, buying, so was more likely to be in the garage reassembling the operating model and putting it back together again.

“He knows what the customer wants, how to merchandise it, how to market it and how to find the optimum price point to get product flying off the shelves.”

Another source applauds Ashley’s acquisition strategy: “He always wanted a department store to open up better access to brands. If you think about the sportswear market, Adidas and Nike restrict access. Selfridges get the top stuff and JD Sports a slither. Having House of Fraser gives him access to bigger brands than if he just had Sports Direct.

“He can sell really premium brands through Flannels, then shift excess stock at a lower price point through House of Fraser and do the same again in Sports Direct if he really needs to. He can sell one product, at three different price points, under three different fascias. It’s discounting without having to actually discount in the eyes of the customer. No one else in UK retail has the ability to do that.”

The ultimate disruptor

Ashley’s shift into more premium markets is a far cry from his Sports Direct business, particularly in its formative years. As the noisy neighbour bidding to disrupt the established order of JD, JJB and Allsports – the latter pair ultimately collapsed under the strain of competition – Sports Direct focused on low prices to woo shoppers.

Ashley brought his own philosophy to trading in this market. Rather than focusing on boosting gross margin with higher prices, he reduced prices to an optimum point where he would maximise unit sales.

sports direct southampton lonsdale

Ashley built a wide range of value own brands such as Lonsdale to sell in Sports Direct stores

When big-name brands such as Nike and Adidas offered excess stock, Ashley would snap up as much as he could at the lowest possible price and pass those savings on to shoppers.

However, in keeping with his single-minded, entrepreneurial, self-made character, Ashley wanted to hold his destiny in his hands and not be beholden to the power sports brands. He developed a wide proposition of own brands – way ahead of rivals JD and JJB – with sharp prices that were attractive to budget-conscious shoppers.

“You would see prices and think: ‘They are taking the piss here’,” one former Sports Direct supplier says. “Footballs would be £2.99 and you’d know that price included VAT and a margin. You’d think to yourself: ‘How do you do that?’

“The stores were, and often still are, a mess. But it is a very clever mess – that is entirely deliberate. The impression you get when you walk into a store is that it was all clearance product. Of course, it wasn’t, but it’s just made to look like clearance.”

Ashley didn’t exactly endear himself to his rivals as a result. He was once summoned to the Cheshire home of Allsports chair David Hughes for a meeting about the pricing of a new Manchester United shirt. It was there that Dave Whelan, the boss of JJB at the time, famously told Ashley: “There’s a club in the North son, and you’re not part of it.”

“Mike being Mike, he didn’t care,” an ally of Ashley’s recalls. “If they would have ‘accepted’ him, would he have engaged in similar tactics? He’s a volume discounter to the core, so I’d like to think not.

“But as soon as he was told that, it ignited an even bigger fire in his belly to take them on and beat them by doing things his way.”

He did exactly that. Ashley exposed the ‘club in the North’ to the Office of Fair Trading (OFT) for price-fixing replica football shirts in 2003. The OFT fined 10 businesses, including Manchester United, for their part in the scandal. JJB was fined £6.3m and Allsports was forced to pay £1.4m.

Ruthless or misunderstood?

Those close to Ashley insist he “gets the blame rather than the credit” for uncovering that “cartel” and “fundamentally changing the sportswear market almost single-handedly”. One goes so far as to describe him as “the original customer champion” and “the ultimate disruptor” – a far cry from more familiar monikers like ’the king of zero-hours contracts’.

His confidants argue the mogul is misunderstood and the real Ashley will never be accurately portrayed by the media.

Mike Ashley at HCLG committee

Ashley has been a vocal champion of the high street and challenged MPs

“He’s quite unorthodox and he’s clearly not to everyone’s taste, to put it politely,” one landlord says. “But the side you don’t read about is that he’s very chatty, very funny, very helpful and reasonably humble.

“I find Mike really straightforward to deal with. He knows what he wants, and he tells you straight off the bat. Then it’s up to you whether you like it or lump it. If you are straight with him, he respects that and you can have a decent working relationship.”

As his empire has grown, Ashley has increasingly become more vocal in championing retail. In front of MPs last December to discuss the future of the high street, he passionately implored ministers to “grab the bull by the horns” to help bricks-and-mortar businesses. That earned him the rare fillip of some good PR. Some believe he deserves more.

When Sports Direct rescued House of Fraser from administration, for instance, one small, family-run supplier was in a precarious position. Around 75% of its revenue came through House of Fraser and with its future relationship with the department store under threat, its existence hung in the balance.

The story goes that Ashley met the family within days of taking control. He reassured them he wanted to continue doing business and stumped up a six-figure sum almost immediately as a sign of good faith, saving the company from financial ruin.

Some landlords tell the tale, but Ashley is reluctant to do so, in keeping with his private persona.

Instead, it is his image as a ruthless businessman that has come to dominate the media – though he still fuels this fire.

debenhams watford

Ashley was aggressive but unsuccessful trying to acquire Debenhams

As part of his aggressive and unsuccessful pursuit of Debenhams, Sports Direct ousted both chair Sir Ian Cheshire and chief executive Sergio Bucher.

Ashley made several attempts to prevent the business collapsing into administration and later called the manner in which it fell into the hands of its lenders, leaving shareholders like Sports Direct penniless, a “national scandal”. Even now, Ashley is turning the screw by backing a challenge to Debenhams’ proposed CVA through the courts.

Ashley had a vision to bring together Debenhams and House of Fraser. Synergies in terms of buying, property and people are there for all to see. The attractions of some of his other interests, such as Agent Provocateur, Sofa.com, Findel and Goals Soccer Centres, have perhaps been less apparent. Some say he simply loves the thrill of the chase, the negotiation and the buzz of getting a good deal.

One source says this sums up Ashley’s approach to life more generally. “Everything is a transaction to Mike. Everything is a marketplace,” the former adviser says. “He is, without a shadow of a doubt – even more so than Philip Green – the man who best understands the price of everything and how much money he can make out of it.”

Even when Ashley reconciled with his ex-wife Linda in 2016 – after shelling out £50m in one of the UK’s largest-ever divorce settlements in 2003 – Ashley is said to have joked to pals: “I got a good deal there, didn’t I?”

Ashley met Swedish-born Linda when he was still in his early twenties and, despite his prominence as a businessman and owner of Newcastle United, has managed to keep her and their three children out of the public eye.

Ashley has spent lavishly on giving them the best possible life and they regularly escape to holiday homes in Florida, Majorca and Swiss ski resort Verbier, but few could pick them out of a crowd.

Work hard, play hard 

The lavish, behind-closed-doors lifestyle his family lead is in keeping with Ashley’s ‘work hard, play hard’ approach to business.

“He’s self-made and that comes across in the way he operates. He’s achieved everything he has through hard work and being ruthless if he needs to be,” Dalgleish says. “If you work at Sports Direct, you have to work very hard. They don’t stop – it’s genuinely 24/7.”

Historically, Ashley and his board would cram five days of work into three at its Shirebrook HQ between Monday and Wednesday – a culture that often resulted in early mornings and “embarrassingly late” finishes, with the working hours often extending beyond midnight.

On Thursday mornings, they would travel to the City for investor events, broader strategic discussions and the Friday board meeting. But Thursday was always “the party night”, one former adviser says – although they would usually be confined to “some s**thole in Soho” where Ashley was less likely to be recognised.

Mike Ashley going through a security check in which he produced a wad of £50 notes from his pocket

Mike Ashley has faced greater scrutiny since Sports Direct went public in 2007

“Those nights descended into a lurid beer-up,” he adds. “It was always heavy – and Mike didn’t like it when you tried to leave. The tactic was always to try to leave with your dignity intact, but he would get very grumpy when you tried to go home, even at 2am or 3am.”

In time, attendees from outside the Sports Direct business grew acutely aware of why Ashley was so keen for them to stay out as late, and drink as much, as possible. One source suggests Ashley’s motivation was “he wanted something on you that he could leverage in the future”. 

The insider references the time Ashley took out a newspaper football correspondent who had been particularly negative about how he was running Newcastle United.

“They took this guy out, got him drunk and got a few photos of him in a compromising position. The coverage changed pretty quickly after that,” he says.

Ashley has built something of a reputation for himself as a big drinker, embellished by Blue’s revelations during their legal wrangle. “You don’t want to get into a drinking competition with Mike. I’ve seen people try in the past and it’s not pretty,” one source says.

But those escapades have often come at a cost, particularly as they fell the night before Sports Direct’s Friday board meetings. Ashley allegedly turned up to one board meeting so hungover he had to lie down under the table to avoid the sunlight pouring through the window.

City life

One glare Ashley can’t avoid, no matter how much of a headache it gives him, is the City spotlight – which is increasingly shining on him following the postponement of Sports Direct’s full-year results.

It blamed the delay on “complexities” borne out of its acquisition of House of Fraser and integrating the business into its financial figures. It spooked the market, sparking a 10% slump in its share price last week.

Even prior to that bombshell, Ashley was described as “Marmite” in the City. In 2007, he infamously dubbed investors “a bunch of cry-babies” after the Sports Direct share price lost almost a quarter of its value in the three months following its float. The comment epitomises his approach to the financial community.

Sports Direct London

Sports Direct could delay its full-year results for over a month

“The float was always just a means to an end for him,” says one former adviser, who explains that Ashley thought becoming a Plc would make Sports Direct more respectable in the eyes of businesses he wanted to buy.

“There’s always been a bit of friction between him and the market, but quite a few people in the City like that he is refreshingly straightforward to deal with. He’s a normal bloke, an entrepreneur, a market trader made good – and investors respect that,” they add.

As a result, investors have backed Ashley despite him not being the polished politician many modern business leaders in the public arena have to be.

One City source says: “You know what you’re getting yourself into. You’re buying into Mike as a man as much as you’re buying into Sports Direct as a business. If you’re not ready for the rollercoaster that comes with that then there’s no point investing.”

It is a rollercoaster that appears to be facing a steep drop. Delaying the financial results served as a fresh blow to Sports Direct, just weeks after the exits of Byers and company secretary Cameron Olsen, two of Ashley’s long-term allies.

Following the departures of Hellawell and Forsey – the man who was, in his own words, employed to “protect” Ashley – the inner circle is shrinking, at a time when Ashley’s retail empire is bigger than ever.

Norman Pickavance, a former adviser to Sports Direct, believes it has left the business in a vulnerable position.

“To run all the businesses they’ve now got with the size of team they’ve got is one heck of an undertaking,” he suggests. “It’s an incredibly stretched team and when you take out a key player like Karen, who has been the queen of the retail operation making all the decisions, there must be a lot of tension there.

“Sports Direct broke the mould a bit in terms of a Plc. The leadership team did things on their own and didn’t bring in many non-executives. That was fine and everyone was happy, as long as they were delivering the money.

“To me, that’s the biggest risk to Sports Direct and any shareholder. They’ve had a huge amount of faith in [Ashley] until now because on the one hand, he’s a genius, but then you look at the corporate governance, the size of the team and the lack of an obvious succession plan, and there are a lot of questions.”

But underestimate Ashley at your peril – just ask Whelan, Hughes, Blue and Cheshire. Only a brave person would bet against him coming up with the answers again.