The bizarre way potential new Sheffield Wednesday or Derby County owner Mike Ashley once settled a £200k legal bill | OneFootball

Ashley returns to the takeover market - this time, no drinking games required.

Sheffield Wednesday’s search for new ownership has reached its decisive phase, with administrators assessing multiple bids for a club mired in crisis.

Mike Ashley, who is also circling Derby County once again, is among the most prominent contenders in the frame.

His initial £20m offer for Wednesday has already been rejected, with administrators now focusing on bids exceeding £30m and requiring proof of at least £50m in available funds to ensure long-term stability.

As competition intensifies and interest in both Yorkshire and the East Midlands builds, Ashley has positioned himself at the centre of two parallel takeover battles that could reshape the next chapter of his footballing career.

Mike Ashley’s unconventional business methods as he eyes Derby County, Sheffield Wednesday takeovers

To understand Ashley’s interest in the Owls and the Rams, it is necessary first to understand the methods of the man himself.

Few British businessmen have cultivated a public persona as contradictory, chaotic and compelling.

One anecdote encapsulates the mythology: the court case involving former adviser Jeff Blue, during which it emerged that Ashley had once attempted to settle a £200,000 legal bill through a drinking game - a marathon session of badly calibrated judgement, which he lost.

It was a story that generated headlines, yet it did not surprise those who have observed Ashley’s approach more closely.

This is a man who, after testifying before a parliamentary committee, reportedly headed straight to a favourite Chelsea pub to sink pints rather than consult advisers or review footage.

He has been photographed drinking with supporters in away ends and tossing aside his tie after public hearings.

His world blends retail aggression with pub-backroom informality, yet the courtroom view of Ashley in the Jeff Blue trial was more nuanced.

Mr Justice Leggatt, presiding over the case, concluded that despite his “unorthodox ways” and the colourful stories surrounding him, Ashley is a “serious businessman” whose work ethic drives the culture of Frasers Group.

The empire he built from a single store in 1982 to an 800-store multinational, alongside the acquisition of Newcastle United and House of Fraser, reflects not luck but relentless commercial instinct.

Ashley’s unpredictability masks a more relevant truth: he specialises in distressed assets. In recent years he has pursued Derby, Reading and Coventry City, consistently circling clubs in difficulty where his liquidity and decisiveness give him an advantage.

His renewed interest in Derby - resurfacing just as he bids for Wednesday - demonstrates that his ambitions in football remain active, opportunistic and wide-ranging.

Hillsborough and Pride Park become parallel fronts in English football’s takeover market

As Wednesday’s administrators push toward selecting a preferred bidder, Ashley’s simultaneous positioning around Derby offers a revealing insight into his strategy.

Reporting from Alan Nixon indicates that Ashley is among several figures - including US multi-club owner John Textor and professional gambler-turned-data-entrepreneur James Bord - who have expressed interest in acquiring Derby.

Textor has also been repeatedly linked to a takeover in South Yorkshire, but is now reportedly out of the frame.

Ashley previously attempted to buy the Rams during their 2022 crisis and is now reportedly circling again.

However, with Derby valued at around £60m and his Wednesday bid already dismissed as too low, there are questions about whether he would meet, or be willing to meet, Pride Park’s asking price.

His pattern is clear: identify undervalued clubs, bid aggressively and walk away if the terms no longer suit him. For Wednesday’s administrators, that approach may be both an asset and a warning.

The Owls remain an attractive but fragile prospect. Administrators Begbies Traynor have confirmed that six bidders - from an initial group of at least 11 who showed proof of funds - are now preparing final offers.

A minimum £30m price has been set to satisfy tax obligations and pay football creditors, while former owner Dejphon Chansiri stands to receive £15m from any sale.

Wednesday’s fanbase, the ownership of Hillsborough and the Middlewood Road training ground and the scale of the club’s identity ensure strong interest. But with the team 27 points from Championship safety, the next owner will not only buy the club - they will be tasked with rebuilding it.

Ashley has both the capital and the appetite. What he has not yet demonstrated is whether he is willing to adjust his methods - or his funds - to secure the deal.