Mike Ashley is as well-known as he is reclusive. For someone who shuns the spotlight, he has made a very public mark in the world of sports. He avoids the trappings of a businessman, preferring to wear a track suit instead of a business suit, and he carries a plastic bag instead of a briefcase.

How did this quiet, very private man found sport retailer Sports Direct and become the 15th wealthiest person in Britain? Let’s look at the unusual journey that has made Mike Ashley the legend he is today.

Humble Beginnings

Ashley started as a squash player and then became a squash coach. He started a sports and ski shop in 1982, relying on a £10,000 loan from his family, and then opened additional shops in London. By 1990, he had opened 100 stores in the U.K.

Near the end of the 1990s decade, Ashley rebranded his stores as “Sports Soccer.” However, organic growth of his shops is not what made him the wealthy man he is today.

Acquisitions, Divorce, & Sports Direct

He began acquiring brands. He bought Donnay in 1996 and Lillywhites in 2002, then bought Lonsdale. These were sellers who were having financial difficulties.

The year 2003 also saw a divorce between Ashley and his wife. The divorce settlement was one of the largest ever in England’s history, requiring Ashley to give up a 16-bedroom home and additional assets valued at £50m.

In 2004, Ashley bought Carlton, Dunlop, Slazenger, and Karrimor.

This began a period of rapid acquisitions that occurred from 2005 through 2012. Companies acquired in this period were Campri, LA Gear, No Fear, Title, Voodoo Dolls, Kangol, Everlast Worldwide, Field & Trek, Sport 2000, USC, Cruise, Van Mildert, Firetrap, No Fear, Hot Tuna, Eybl, Debenhams and HoF.

Sports Direct International PLC was listed on the London Stock Exchange in 2007.

Team Ownership

Ashley is probably most known as the owner of the Newcastle United team. He paid approximately £135 million to purchase the team. However, his status as a rich team owner did not change him. He became known for sitting in the stands with fans of the club. The team won the championship in 2017.

He also owns a stake in the Rangers, a Scottish football team.

An Abandoned Drunken Offer

A man named Jeffrey Blue, an investment banker, took Ashley to court, claiming Ashley had promised to give him £14m if he could increase the share price of the company that owns the Newcastle club.

Details revealed in the trial showed that Ashley and Blue had been drinking heavily at a pub, and that the offer was not meant to be taken seriously. The court agreed, and Ashley did not have to pay the money.

Whistleblowing

In 2000, Ashley turned on industry competitors by becoming a whistleblower, giving evidence that many sports gear sellers had colluded in price fixing on jerseys and shirts.

Eccentricity

Ashley has been described as an unusual businessman, conducting business in strange places, in unorthodox ways. That, in addition to his impulse to be reclusive, has given him a kind of legendary status. Rumors swirl about his net worth and stakes in other businesses.

The Bottom Line

Whatever the future may bring for Sports Direct, Mike Ashley himself, and Newcastle United, it is likely there will be more mystery, eccentricity, and notoriety. The public keeps up with Ashley’s adventures, even though he does not seek headlines. His journey from squash player to world-class entrepreneur has made him a bit of a folk hero. In spite of his unusual personality, or perhaps because of it, he has managed to become extremely wealthy and successful.