For comparison, this where Ashley allegedly lives today. He's come a long way.
One eagle-eyed local called Jules has taken photos of what is believed to be Ashley's home in Tottering, and published them on Flickr. Apparently, Ashley has a penchant for epic Christmas lighting at his North London village home.
Ashley's original plan was to become a pro squash player, but he was injured at 16. (It's not clear what, exactly, the injury was.)
After telling teachers he would 'run his own shop one day,' he opened his first location in 1981.
In the 36 years since, Ashley built that shop into a retail empire, Sports Direct. The chain is known for its pile-em-high, sell-em-cheap approach to sportswear.
The Sports Direct chain IPO'd in 2006. It was once worth £4.3 ($6.6) billion but its market cap has fallen to nearer £1.5 billion.
Ashley is still the majority owner in Sports Direct and has ownership stakes in other sports, outdoor and apparel companies.
His purchases have included Donnay, Dunlop Slazenger, Karrimor, Kangol, Agent Provocateur, and boxing brand Lonsdale. Ashley also has a massive stake in Blacks Leisure Group, the owner of Millets and Mambo.
Ashley dislikes public attention. But when he gets into the mood he can put on a real performance. He once made headlines by doing a striptease in a Chinese restaurant in 2011.
"He’d sunk a few pints,” a guest at the restaurant said. At the end of the evening, Ashley paid the £2,000 bill in cash. Check out the full story in the Mirror here.
In a strange way, that night at the Chinese restaurant is typical of Ashley: He hates attention but nonetheless still manages to do things that attract it.
I'd be like Mike Ashley if I had sold Moussa Sissoko for £30m as well. pic.twitter.com/hhOvmdFEZp
— Footy Accumulators (@FootyAccums) July 3, 2017Currently, Ashley commutes either using helicopters or a Dassault Falcon 7X private jet. Sports Direct acquired the plane for the management team at the end of 2016. It cost the company $51.1 million.
He may be a billionaire but he has been seen using plastic bags as a briefcase.
According to the Herald Scotland, "he often wears scuffed jeans, with his shirt either rumpled or hanging out, and has been seen to carry his mobile phone and wallet in a plastic bag."
He also has a habit of carrying a lot of cash. At a press event intended to show that Sports Direct distribution centres were not like Victorian workhouses, he dumped a huge roll of £50 notes into the tray at the security gate. He had just arrived from a casino, he said.
Ashley admits he is a "PR nightmare" because of this kind of thing.
This was the same place where one of his workers gave birth to a child in a warehouse toilet, for fear of missing work. This is a photo from inside the site.
Ashley likes to stay up late. He once spent £125,000 on champagne at the Pink Elephant nightclub in New York in 2008, on a night out with friends. The club's emblem is this mascot.
He also reportedly lost £1 ($1.5) million in two hours on the craps tables at London's Aspers Casino in 2011.
He likes a drink, too: This video of Ashley downing a pint at a football match in less than 10 seconds is legendary.
Ashley likes to mingle with Newcastle fans occasionally.
Ashley is "just one of the lads," according to one fan called 'Beefy' (real name Keith Roberts) who spoke to NUFC.com and posted a picture online. "He was just walking past in the ground on his way to his seat and I said can I have my photo taken with you," said Roberts. "I lifted my top and he just said to me, 'Well you’ve got your belly out then I’ll have to get mine out.'"
Newcastle fans turned on Ashley when the club was relegated. Some started to boycott the games. But Newcastle has earned promotion back to the Premier League — giving Ashley more time in charge of the club.
In 2014, he bought a portion of Scottish club Rangers FC but was prevented from increasing the stake due to a conflict of interest with his ownership of Newcastle United.
Sometimes he is ruthless. He ratted out his rivals in 2000, when he told the Office of Fair Trading that other companies were trying to fix the price of football shirts.
But he doesn't always have the Midas Touch. In 2008 he lost around £300 ($461) million after HBOS bank collapsed following the credit crisis.
Parliament once summoned Ashley to answer questions about working conditions at his warehouses. For months, he refused to show up, risking a charge of contempt and a prison sentence. He called MPs "a joke." (He did eventually appear, in 2016.)
Ashley found his name back in the news for several reasons in 2017. Chief among them were reports of a 2013 meeting at the Horse and Groom pub in Great Portland Street, London, with Jeff Blue, a former Merrill Lynch banker.
In a lawsuit — which Ashley ultimately won — Blue claimed the Sports Direct owner promised to pay him £15 million if he could get Sports Direct's stock to double from £4 to £8 a share.
Blue's plan was to persuade investors in The City that the stock should not be avoided. The stock did eventually hit £8, but Ashley allegedly only paid £1 million. Ashley denied the claims, but admitted "a considerable amount of alcohol" was drunk that night.
Blue claims that Ashley regularly did business while in pubs, casinos, and restaurants. He once threw a lavish dinner at Benares in Mayfair, where his board of directors drank the restaurant's entire supply of £3,000-a-bottle Richebourg wine before heading to a casino, Blue alleges in the suit.
Blue also claims that Ashley once held a board meeting at a pub in Alfreton. At that meeting, Ashley allegedly challenged a bank analyst to a drinking competition.
After allegedly drinking 12 pints of beer coupled with vodka chasers, Ashley allegedly "vomited into the fireplace located in the centre of the bar, to huge applause from his senior management team." Ashley denied the claims and won the case.