Mike Ashley: Is he Really Football’s biggest high roller?

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If you’re not overly familiar with the billionaire Mike Ashley, the chances are that you’re not alone. After all, this intensely private entrepreneur prefers to stay out of the limelight, despite his standing as the current owner of Premier League side Newcastle United.

Still, when Ashley does make headlines, they tend to be memorable ones. In fact, his stint as owner of Newcastle has been marred by conflict and controversy, while he has also earned a reputation as something of a gambler during his time on Tyneside.

In this post, we’ll take a closer look at the man himself, while asking how he earned his reputation as the man most likely to roll the dice?


Who is Mike Ashley?

Like a great number of successful entrepreneurs, Ashley left school at 16, at which time he was a talented, county-level squash player. Injury ended his dreams of a sporting career, however, so he became a coach before venturing into the world of private business.

Here, he rolled the dice for this first time, borrowing £10,000 (or £31,500 when adjusted for inflation) from his family to open a sportswear and ski shop in Maidenhead.

Ashley took the calculated risk of continuing to take on private investment, and by the late 1990s he owned more than 100 UK stores and had created the ‘Sports Soccer’ brand. In the two decades since, he has built a vast empire of business concerns, with his holding company Sports Direct International Plc. boasting over 400 UK-based stores and several well-known brands.

Given this success, Ashely has gambled further by buying up failing brands and rebuilding struggling businesses, with high profile acquisitions including Donnay, Dunlop Slazenger and Kangol. These brands were procured at a discounted rate, before Ashley used his know-how and resources to reverse their fortunes.


Is Ashley Really a Gambling Man?

Perhaps Ashley’s biggest punt to date was the purchase of Newcastle United in 2007, when he paid £135 million of his personal fortune to assume ownership. This represented a huge risk for a man who is notoriously introverted and private, as buying such a high profile club automatically propelled Ashley into the public eye.

This type of gamble betrays Ashley’s appetite for risk, which some may argue is inherent to all true entrepreneurs. It is by no means the only indication of the sportswear magnate’s love of gambling, however, with other stories having served to strengthen his reputation as football’s biggest risk-taker.

In 2008, and barely a year after taking control at St. James Park, Britain’s 54th richest man with assets totalling £1.5 billion scooped a staggering £1.3 million while playing roulette at the exclusive Fifty London casino in Mayfair.

mike ashley roulette

During one incredible, 15-minute session, Ashley staked bets worth £480,000 around his lucky number (17), before leaving the table almost £1 million richer than when he walked in. Apparently, the billionaire left the table to a round of applause after his explosive entrance, with his efforts having passed into folklore in the gambling realm.

This represents an incredible return for just a quarter of an hour, and there’s no doubt that Ashley is willing to stake huge amounts of his own cash in the pursuit of huge rewards.

Newcastle fans may argue that Ashley’s love of gambling is contradicted by his refusal to invest in the playing squad, which has caused a great of tension between the owner and season ticket holders in recent times. However, it cannot be denied that Ashley is a shrewd businessman, and it appears as though he is deliberately adopting a more conservative approach with the club’s capital in order to safeguards Newcastle’s interests over time.

In truth, this represents good business sense, and simply highlight’s Ashley’s ability to separate his private funds from those that belong to the football club and its share-holders.


The Last Word

If you look at Ashely’s entrepreneurial background, you see a man who has always been willing to take measured and calculated risks in pursuit of his goals.

He also continues this ethos in his private life, with his inherent love of gambling anchored by a sharp business mind and a desire not to wager more than he can ever afford to lose. Herein lies the essence of every successful gambler, as each individual risk must be calculated and structured to minimise the impact if things go awry.

In this respect, Ashley is a typical high-roller, as while he has a gambler’s instinct this will never overcome his innate business sense and desire to achieve a profit. He’s certainly one of the biggest gambler’s in the world of football, however, and one who continues to remain something of an enigma in the public space.


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