While once his decisions went unquestioned, now everything he does at the Gunners is coming under the spotlight.
Right formula eluding alchemist Arsene Wenger
It was the sort of fraught, uneasy media briefing that has become commonplace for a man who was once the most compelling talker in the Premier League.
As Arsene Wenger chided his audience for discussing transfers rather than football, he was asked if a summer in which his two most creative players walked out on him while a once-devoted support openly doubted his judgement was his hardest at Arsenal.
"It's easier to win championships, cups and be unbeaten than be questioned," Wenger said. Perhaps the query should have been about the hardest period of the Frenchman's career.
It is almost 17 years since Wenger was dismissed as coach of Monaco. League champions in the not too distant past, his team had underperformed the previous season and his decisions were questioned.
They began the 1994/95 campaign with injuries to key players and unprepared talent (including a teenage Thierry Henry) deputising.
Seven league games, and four defeats, later Wenger was gone from the principality, regretting a decision to turn down the Bayern Munich job a few months before.
Handicapped by the callowness of his squad, he is already five points adrift of Manchester United, recognising that "it is vital for us to have a very good game".
With a mere five victories in 18 matches, stretching back to February's traumatic Carling Cup final loss to Birmingham City, there have been few good performances these past six months.
Wenger spent much of the summer pondering an invitation to head up a prodigiously funded Qatari takeover of Paris St-Germain.
At Arsenal his once unparalleled power has leaked away to Stan Kroenke, a new owner whose sustained support cannot be taken for granted.
The discontent is telling. Concerned that his talent might never be translated into trophies, Cesc Fabregas pushed so hard to leave that the club let him go at less than what they considered market value. If he spoke generously of Arsenal upon joining Barcelona, Samir Nasri indulged no such niceties.
Voicing a concern that did not depart the Arsenal dressing room with his transfer to Manchester City, the Frenchman explained his decision to leave as a consequence of the club's failure to strengthen around him.
"I started talks about a contract extension last October," Nasri said. "But June came around and I had not heard any news and I could not see any players being brought in during the transfer window. At a given point you have to make an investment."
In the background were concerns about training methods and the physical preparation of a team that has suffered disproportionately from injuries of late.
As worrying as the grumbles of Wenger's principal players are the concerns of those who have assisted his management for years.
They talk of a man who has changed amid off-field turbulence. They despair at the negativity surrounding a summer in which the board has urged Wenger to spend on the first team but not put in place the sort of pay scale that could prevent another Nasri happening. (Arsenal's complex wage structure topped out around £125,000 (Dh750,000) a week for Fabregas, well behind Manchester United, Chelsea and Manchester City).
The sense is of a lack of direction, of a once-coherent club now ill at ease with itself.
Arsenal Supporters' Trust carefully monitors the club's financial accounts and believe Wenger could commit £80m to transfers and wages in the final days of this window without going into the red. It is an extraordinary reserve of resources for a self-funded football club, yet no one expects it to be fully used.
Wenger dislikes being quizzed on transfers but does not help himself by sending out contradictory messages.
On Friday he talked of United being favourites for the title and how Arsenal could prevent them from retaining it.
"At the moment we are a bit short, number-wise, but if we get two or three players in we have the quality to challenge them," Wenger said. A few minutes later he stated it was possible he might not sign anyone.
Arsenal have indulged in low-ball bids for Phil Jagielka, Gary Cahill, and a bizarre request to take Marseille's elite midfielder, Lucho Gonzalez, on loan that drew the ired of his current employers.
Though Wenger insists he was "involved" in deciding the scope of those offers, the engagement of the London law firm Slaughter and May in transfer business has raised eyebrows.
Wenger recognises he needs another striker, has bid for centre backs and is in the market for a midfielder. The France international Yann M'Vila is one impressive target but Rennes say they will not sell for less than €26 million (Dh137.8m). Had Arsenal moved before his end-of-season contract renewal, M'Vila would not be so expensive.
At Sochaux, a player considered Nasri's equal is similarly highly valued. Marvin Martin would love to join up but does not expect to be allowed to. "I've said I wanted to go," said Martin. "It hasn't happened for the moment and, personally, I think I'm going to stay."
It is not a question of identifying talent; Wenger's major purchase to date, Gervinho, has started well. It is about securing and retaining it.
In the past, Wenger was renowned for selling players just as they began to decline. With Fabregas and Nasri such control has gone.
There are two interpretations of the process: either Wenger was blind-sided by his board or he misjudged the mindset of his players.
What is clear is that senior Arsenal executives had placed an asking price of €25m on the Frenchman's head before Wenger's now infamous request to "imagine the worst situation - we lose Fabregas and Nasri. You cannot convince people you are ambitious after that … You cannot pretend you are a big club".
Wenger's explanation of his early July dogmatism is tortuous.
"I did not say that in the way that we are not a big club.
"I said that the other big clubs can come and take our best assets. Fabregas was a very special case where we sold the player below market because he wanted absolutely to go there.
"The second decision we had our back to the wall because [Nasri] had one year left on his contract and didn't want to extend the contract. The second decision was more a financial decision."
More are headed Arsenal's way. Theo Walcott politely rejected inquiries from Chelsea this summer in the knowledge that by the end of this season his contract will be down to a final, high-leverage year.
Newly installed captain Robin van Persie will be similarly vulnerable to external enticements or internal disgruntlement.
Through Fabregas, William Gallas, Gilberto Silva, Thierry Henry and Patrick Vieira, Wenger's team leaders now habitually exit stage right. And the rate of change is accelerating.
Amid it at all Wenger cites spurious "official analysis" of referee's decisions that cost Arsenal a runners-up place last season, and complains of press negativity.
Together with the club he bans L'Equipe from a Champions League match after an errant news story, and cancels national newspaper access, offering controlled content from the club website instead.
Arsenal are bleeding and no one is healing the wounds.