Welcome to today's episode called Mike Ashley: Ruthless, Reckless, Chaotic and Cunning, and for all non-Irish and UK listeners who mightn’t be aware of Mike Ashley, the billionaire retailer, then you're really in for a treat. From alcohol-fueled meetings to corporate espionage, this story of one of the UK’s most successful businessmen is a cracker. Enjoy.
Mike Ashley: A Corporate Drama Worth Watching
Mike Ashley—retail tycoon, controversial personality—and we’re going to get into his story, but I want to kick things off by looking at a corporate espionage scandal happening at the online retailer Boohoo, where Ashley is a major stakeholder and a potential power-grabber.
Boohoo’s Meteoric Rise
Let’s rewind a bit and look at Boohoo’s origin story. Back in 2006, Mahmud Kamani and Carol Kane launched the brand from Manchester, offering affordable, trendy clothing exclusively online. It was an instant hit. By 2014, Boohoo went public, continued to grow, and in the process scooped up big names like Debenhams, Karen Millen, and PrettyLittleThing (or PLT, for the cool kids). Here’s an interesting tidbit: PLT was founded in 2012 by Kamani’s sons, and Boohoo bought a 34% stake in 2020 for $339 million, valuing the brand at over $1 billion. Mmmm… can I interest anyone in a conflict of interest? At its peak during the pandemic, Boohoo’s total worth soared to $5.8 billion.
When the Scandals Hit
But what goes up must come down, and for Boohoo, the fall began in 2020 with a pretty serious labor scandal. A report revealed really low wages at a Leicester factory supplying Boohoo—workers earning as little as £3.50 an hour, less than half the minimum wage at that time, and working in grim, unsafe conditions, all during the height of the COVID-19 pandemic.
The market’s reaction was brutal. Boohoo’s value plummeted by more than $1.5 billion in just days, and the company’s reputation took a serious hit.
The Downward Spiral
Fast forward to today, and Boohoo is struggling. From its pandemic peak in June 2020, the company’s value has nosedived by over 90%, leaving it with a market cap of just $390 million at the time of recording. The reasons are clear: post-pandemic shopping trends shifted back to brick-and-mortar stores, and competition from Chinese fast-fashion retailers like Shein and Temu is relentless.
And then there’s Ashley, circling like a shark. His Frasers Group holds a 27% stake in Boohoo, and he’s been inching closer to seizing control.
Espionage Allegations
But here’s where things get a little bit bizarre and kinda scary. In 2024, reports came out that Boohoo executives, including Kamani and current CEO Dan Finley, alleged they’ve been targets of corporate espionage. Surveillance devices were discovered near Boohoo’s headquarters, and executives claim they’ve been tailed in public and even to their own homes. Former CEO John Lyttle reportedly resigned in October 2024 after encountering trespassers on his property. Kamani, meanwhile, has faced alleged physical intimidation, including an assault. Police in Manchester, London, and Kent are investigating, but the details remain murky.
In a bid to ease tensions, Boohoo has offered Frasers Group a single board seat—but they’re keeping Mike Ashley and his ally Mike Lennon out of it for now. With Ashley’s $4.4 billion fortune and his reputation for aggressive takeovers, this standoff is far from resolved.
Let’s roll the clock back to 1982. Mike Ashley was just 18 when he took his first shot at business, opening a sports and ski shop in Maidenhead, a market town about 50 miles outside of London, with a £10,000 loan from his family.
He had a very simple formula: affordable sportswear, sold at scale. By the 1990s, his modest beginnings had snowballed into a rapidly growing chain rebranded as Sports Soccer. By the end of the decade, Ashley had over 100 stores across the UK. In the early 2000s, Ashley gave the chain another makeover, transforming it into Sports Direct International.
Between 2004 and 2012, Ashley went on a shopping spree for distressed brands, snapping up over 20 companies, including Carlton, Dunlop Slazenger, LA Gear, Everlast, Kangol, and Lonsdale.
These weren’t shiny, in-their-prime brands—they were faded stars, past their heyday. But Ashley saw their potential. They still held a glimmer of consumer recognition, and he knew exactly how to leverage that. His strategy was simple but very effective: slap these familiar logos on cheap products made in the Far East, creating what looked like premium goods at very competitive prices.
Even I’ll admit, I fell for it. I remember going into Sports Direct when a store opened nearby and buying Slazenger sports socks at a very good price. Only later did I realize that the socks were bargain-bin quality. As one cynic put it, “Nobody ever lost money underestimating the public’s appetite to buy shite.”
The significant profits he was making from these cheaply manufactured brands allowed him to implement an aggressive pricing strategy on premium brands. While competitors like JJB Sports stuck to manufacturers’ recommended retail prices, Ashley slashed costs without hesitation. Take Adidas’ iconic Predator football boots—while almost all retailers priced them at £119.99, Ashley sold them for £79.99.
By the early 2000s, Ashley had bulldozed past smaller rivals like AllSports, leaving him locked in a heated battle with JJB Sports for dominance. This rivalry hit its peak during the release of new football shirts for the England and Manchester United teams—blockbuster events for the sports retail industry. But Ashley’s relentless discounting sucked the life out of these occasions, leaving competitors seething and scrambling to keep up.
David Hughes, AllSports’ owner, tried to broker peace in 2000. He invited Ashley, JJB’s Dave Whelan, and an Umbro executive to his home, hoping to smooth things over. Whelan had very little regard or respect for Ashley, viewing him as an upstart and not a real threat to his retail empire. The meeting didn’t go well and finished with Whelan uttering the now-famous line: “There’s a club in the north, son, and you’re not part of it,” before storming out and heading back to his helicopter. What Whelan didn’t realise is that Ashley had no interest in joining any club. Whelan also critically underestimated Ashley’s cunning and ruthlessness.
Because straight after that tense meeting, Ashley reported JJB, AllSports, and Umbro to the Office of Fair Trading for price-fixing. The investigation, which dragged on for years, ended with hefty fines for all involved. AllSports eventually folded, and JJB Sports never fully recovered.
By 2006, Ashley’s Sports Direct had overtaken JJB to become the UK’s largest sports retailer. When JJB finally collapsed in 2012, Ashley delivered the coup de grâce, buying its brand name, leftover stock, and 60 stores for a mere £30 million.
But we’re jumping ahead—let’s get back to February 2007. Sports Direct floated on the London Stock Exchange with a valuation of £2.5 billion. Ashley himself pocketed £1.8 billion but held on to a majority stake in the company.
Shares initially priced at £3 tumbled to a mere 30p during the 2008 financial crisis. The media and people in the City were scathing of Ashley’s management style—which we’re going to get into—and the business’s performance, but Ashley brushed off the naysayers as “cry babies.” And, true to form, the shares rebounded, increasing to £8 by 2014.
And it was as a result of the shares reaching £8 that we get this bizarre court case that gives us such a great insight into Mike Ashley.
Let’s set the scene: the Horse and Groom pub in London. It’s a boozy evening, and Mike Ashley is in his element. Somewhere between the pints and the vodka chasers, Ashley turns to investment banker Jeffrey Blue, who has done some work with Ashley over the years, and promises Blue a £15 million bonus if Sports Direct shares hit £8.
Fast-forward to the day the shares actually hit £8, and Blue comes knocking, ready to collect his windfall. Ashley, however, has no intention of paying Blue, and based on all the evidence that I read about it, rightly claims it was nothing more than drunken banter.
When Blue sued for his alleged bonus, the judge didn’t hold back. The case was dismissed, with a particularly cutting observation: “The fact that Mr Blue has since convinced himself that the offer was a serious one, and that a legally binding agreement was made, shows only that the human capacity for wishful thinking knows few bounds.”
To add insult to injury, Blue didn’t just lose the case—he had to pay Ashley’s £1.5 million legal bill, on top of his own fees, which reportedly totalled about £1 million.
But the trial wasn’t just about the alleged £15 million promise. It also dragged Ashley’s unorthodox management style into the spotlight. For starters, there was the revelation that Ashley challenged a young Polish analyst to a drinking competition and proceeded to win by drinking 12 pints of beer, chased with vodka. The session ended with Ashley vomiting into a fireplace.
Witnesses described board meetings as “pub lock-ins,” complete with fish and chips, kebabs, and drinks flowing well past closing time. Ashley himself didn’t shy away from his drinking habits when questioned in court, proudly proclaiming, “I’m a power drinker. My thing is not to drink regularly. It is binge drinking. I am trying to get drunk.” Mission accomplished, Mike.
Former executives painted a vivid picture of late-night strategy sessions held not in corporate boardrooms but in Indian and Chinese restaurants, where they tried to finalize store logistics while dodging curry stains on the blueprints.
And then there’s the famous story of a legal bill—a dispute between Ashley and Merrill Lynch over who would foot a £200,000 bill linked to the 2007 flotation of Sports Direct. The matter was settled by a game of spoof—a simple coin-guessing game—that Ashley ended up losing.
Now, this story has gone down as part of Mike Ashley’s legend, but I’m not 100% convinced about its veracity—whatever about Ashley making that kind of bet—it was his money, after all—but if the story is true, then what happened to the Merrill Lynch banker who won it? It wasn’t his money to bet. Was he promoted or sacked? I couldn’t find out.
In May 2008, he reportedly won £1.3 million in just 15 minutes at a roulette table in London’s Fifty Club.
And one final nugget: if Ashley got bored during a board meeting, he was known to crawl under the table for a nap.
But despite, or maybe as a result of, Ashley's unorthodox management style, throughout the 2000s Ashley kept on building and expanding. By 2019, he had over 400 stores with a workforce of more than 20,000 spread across the UK, Ireland, Belgium, and Slovenia.
2018–2019 also marked a turning point as Ashley rebranded his empire as Frasers Group. This was right after a shopping spree where he scooped up several struggling retailers, including the House of Fraser. Once the crown jewel of the British high street, House of Fraser had been founded back in 1849 and was teetering on the brink of collapse. Ashley swooped in, picking it up for £90 million, but it was a purchase that he soon regretted.
Within a year of the purchase, Ashley admitted that it wasn’t his shrewdest move. “If we had the gift of hindsight, we might have made a different decision,” he said.
Ashley has faced relentless and justified scrutiny over how his business treats its workers. Over the years, allegations of exploitative labour practices have cast a long shadow over his business.
In 2010, a BBC investigation blew the lid off appalling conditions at a Lonsdale factory in Thailand. Workers were crammed into dormitories with 38 people sharing one toilet. Shifts stretched a gruelling 12 hours, with a daily wage of about £1. Injuries weren’t covered by the company, with workers expected to pay their own medical costs. And absences would cost workers a fine equivalent to an entire week’s wages.
Fast-forward to 2016, and things weren’t looking much better at home. A Guardian investigation exposed horrific conditions at Sports Direct’s warehouse in Derbyshire:
Workers were paid below the legal minimum wage.
Conditions were so dire that MPs compared them to a "Victorian workhouse."
The most shocking revelation was that a woman gave birth in a toilet cubicle on-site—she continued working despite being in labour for fear of losing her job.
Union officials reported multiple cases of births, miscarriages, and other pregnancy-related emergencies at the warehouse.
The fallout was brutal. A government inquiry concluded that Ashley’s business model operated on treating workers “without dignity or respect.” Sports Direct—and its temp agencies—were publicly named and shamed. Ashley, in response, admitted to MPs that underpayments had occurred and said that he wasn't aware of the working conditions.
Now, whether he knew about the working conditions, I can’t say. I don’t buy it that he wasn’t aware of the payments issue. Throughout my research, the one thing that is crystal clear about Ashley is that he keeps a forensic eye on costs and has a real talent for numbers. He was known for being aware of how much everything cost, and how much he could sell it for.
Here’s a quote from an associate: “When he looked at numbers, it was like watching Rain Man. He could pick figures out and immediately see where an issue needed fixing.”
So I’m pretty sure that he was well aware of how much his workers were being paid.
For Ashley, the stain on his reputation remains—and rightly so.
In 2007, Ashley made headlines with his £134 million purchase of Newcastle United, a move that quickly turned sour for both him and the club’s fans. It was a hasty decision that was marked by zero due diligence and, as a result, an avalanche of unexpected problems.
Almost immediately after sealing the deal, Ashley unearthed a £57 million stadium debt that needed repayment within 60 days. To steady the ship, he pumped £111 million of his own money into the club as interest-free loans.
Initially, Ashley’s everyman persona—sitting with fans at matches, going for pints with them before and after games—won over supporters. His popularity peaked early when he brought former player and all-round Newcastle football legend Kevin Keegan back as manager in January 2008. But the goodwill didn’t last. Keegan’s acrimonious departure later that year marked a turning point.
Then came Ashley’s baffling decision to rename the hallowed St. James’ Park as the Sports Direct Arena, a move universally panned as crass and tone-deaf. If that wasn’t enough, he plastered the stadium with garish, cheap-looking Sports Direct ads, further alienating Newcastle’s fiercely loyal fanbase. These missteps underscored Ashley’s commercial focus—and his disregard for the club’s traditions and identity.
Crucially, and most unforgivably, under Ashley’s ownership, Newcastle endured two humiliating relegations, in 2009 and 2016—gut-wrenching moments for a club of its stature. Fans increasingly saw his tenure as a “reign of chaos,” defined by poor decision-making and a lack of ambition.
In October 2021, Ashley finally offloaded Newcastle United for £300 million to a consortium led by Saudi Arabia’s Public Investment Fund. For the long-suffering fans, it was the end of an era they were all too eager to forget.
The sale of Newcastle wasn’t just a turning point for the club; it also marked the dawn of a new era at Frasers Group, as Michael Murray, Ashley’s son-in-law, took the reins as Chief Executive in 2022. At just 33, Murray brought a distinctly modern touch to the company.
Murray first joined Frasers in 2015 on a lucrative consulting contract. Over time, he carved out a niche as a modernizer, repairing relationships with premium brands like Nike and Adidas—ties that had frayed under Ashley’s watch.
Central to Murray’s vision is elevating the Flannels brand (Flannels is a chain of high-end stores stocked with premium brands—some of which Frasers has invested in or bought outright, like Gucci, Mulberry, and Hugo Boss) and repositioning Sports Direct’s image. Under Murray, once-drab flagship stores have been transformed into sleek, premium retail spaces—a far cry from Ashley’s “pile ’em high, sell ’em cheap” mantra.
Murray’s changes haven’t come without hurdles. Frasers Group has faced its share of financial setbacks over the last few years, not helped by changes in consumer habits leading to a softening in the luxury market. At the time of recording in April 2025, its market cap stood at $3.18 billion—well below 2021, when it was worth $5.23 billion.
Murray’s personal earnings have also drawn scrutiny. Since joining, he’s pocketed over £33 million in payouts tied to property deals, and his controversial bonus scheme remains a flashpoint. Under the scheme, Murray stands to earn a £100 million bonus if Frasers’ share price doubles to £15 by October 2025—a goal that now feels increasingly out of reach. At the time of recording, shares were priced at just under £6.
Although Ashley has stepped back from day-to-day operations, he still wields significant power as the majority shareholder with a commanding 70% stake. And while Murray looks after the day-to-day running of the business, Ashley continues to make strategic investments in brands and retailers.
Its investment portfolio includes significant stakes in the following:
AO World plc: Electricals retailer
N Brown Group plc: Owner of brands like JD Williams and Simply Be
Currys plc: Another major electrical and computer retailer
Asos plc: Online fast fashion giant
Mulberry Group plc: Luxury handbags
Game Digital plc: Video game retailer
Hugo Boss: High-end fashion
Ashley’s personality is as contradictory as his career.
Despite his ruthless business reputation, many who’ve worked with Ashley describe him as approachable. According to one source: “When I first met him, I thought I’d get a bit of a Philip Green (in other words, brash and arrogant). But actually, he’s courteous and considerate. He asks a question once, and he listens to the answer.”
David Hughes, the former owner of AllSports—one of the retailers Ashley grassed in relation to price-fixing, and who was eventually pushed out of the market—described him bluntly: “Mike has never broken the law. He might have come close a few times, but he is no crook. He is ruthless, though. Vicious, actually.”
While Ashley, without doubt, is a polarizing figure, there’s also no denying he’s an intriguing one. The controversies—particularly the appalling labor practices—leave a dark mark on his legacy, one that shouldn’t be brushed aside. And yet, despite those glaring flaws, there’s something undeniably compelling about him. His approach to business is anything but traditional, rejecting the standard corporate gloss in favor of a raw, unvarnished style. I’ve seen him being interviewed, and I like his honesty—rough around the edges, no pretense, and refreshingly free of the usual airs and graces.
I still haven’t made up my mind about him—and we’re going to be hearing a lot more of him. That’s what makes him such a great business story. I hope you’ve enjoyed it as much as I have, and remember, if you have any comments, any corrections, or any story that you’d like us to cover, email us at: info@gbspod.com
All the best, folks.