The Frenchman has won more trophies than any other Arsenal manager, presided over more games than any other Arsenal manager, and is universally accredited with instilling a footballing philosophy at the club that is envied the world over.
And yet many believe Wenger is a man under severe pressure as he prepares for his 16th season in north London.
Trophyless for six years and counting, a recent transfer record best described as book-balancing, and now having to cope with the likely departures of two of his biggest stars, Wenger is dealing with disillusionment and frustration among the club's support on a scale he has never had to before.
Simply put, is this Wenger's make-or-break season?
"This is a period of real uncertainty at the club," former Gunner Nigel Winterburn told BBC Sport. "No-one has the divine right to win anything, but it has been far too long since Arsenal won any sort of trophy and the fans are getting restless."
"There's a sense of real worry around the club."
"The building process of the last few years looks to be faltering, the team is breaking up and the club have so far failed to make any great waves in the transfer market."
"I believe Arsene is still the right man for the club - but I can also see it from the other side and appreciate the fans' frustrations."
"Arsene and the club need to win a trophy very, very quickly."
The disaffection of a large section of Arsenal supporters was evident at the end of last season when the team were booed off after their season-ending match against Aston Villa - following a campaign that had seen the club go so near and then fall short in all four competitons - and again when the team was jeered during a recent pre-season friendly draw against the New York Red Bulls.
But it is quite a turnaround for Wenger - a man who, not long ago, appeared untouchable at the club, when his early successes combined with a footballing revolution that cast the dour and pragmatic "boring, boring Arsenal" image firmly into the past to help lend the Frenchman almost unrivalled security.
With Thierry Henry leading the eulogies, and then vice-chairman David Dein claiming Wenger had a "job for life", few could have imagined then a time when the former Monaco coach would not be universally adored on the Gunners' terraces.
Things change quickly in football, though.
"Never forget that Arsene is a winner - that is his biggest quality - and he has done an amazing job," Lee Dixon told BBC Sport.
"But there's no doubt the fans are getting more and more restless. There needs to be an improvement this year and no-one knows that better than Arsene, I'm sure."
For many, the frustration is a result of Wenger and the club's spending policy.
Working under the club's restrictions of self-sufficiency, Wenger has steadfastly refused to spend beyond the club's means, preferring instead to rely on developing the young players at the club and breeding an ethos of a team collective.
Few could argue the results have not at times been good to watch - but recent frustrations appeared to prompt something of a rethink this summer, with Wenger pledging to be "very active" in the transfer market, a sentiment echoed by chief executive Ivan Gazidis who predicted it would be "a very busy close season".
So far, however, just Gervinho, Alex Oxlade-Chamberlain and youth defender Carl Jenkinson have been added to the squad, leaving Arsenal fans bemused by the club's failure to add defensive signings to the ranks.
"Looking at where Arsenal have let themselves down in the past couple of seasons, it's clear where their frailties lie: defensively," added Winterburn.
"You look at the back four, the keeper, the protection in front of the defence - it just isn't good enough. I compare this side to the Arsenal team I played in and while the current one undoubtedly has more ability, in terms of desire, organisation and strength it is way behind.
"Arsenal absolutely need to strengthen in the next month otherwise they are going to struggle."
Alex Fynn, author of "Arsenal - The Making of a Modern Superclub", told BBC Sport: "The defects have been palpably obvious for some time, more than two years, and still those areas haven't been addressed.
"Fans and experts alike are agreed: why hasn't Wenger strengthened the defence?
"And it's not just that, either. What concerns fans are the missed opportunities. The opportunity to sign Mark Schwarzer or Shay Given was passed up. The opportunity to sign Xabi Alonso was passed up. The opportunity to sign an English-type centre-half has been passed up year after year. A lot of fans are worried."
It would be unfair to assume all is lost for Arsenal and Wenger, of course.
The departures of Nasri and Fabregas could hit Arsenal hard this season Winterburn remains a firm believer that Wenger is still the right man to manage the club, Neville calls the Frenchman "one of the very best", while Dein - Wenger's biggest ally during his time at the club until 2007 - echoed those sentiments on BBC Radio 5 Live last Sunday.
"People have to remember what he's achieved," he said. "You under-rate Arsene at your peril."
Publicly, too, the 61-year-old has the backing of the club, even if new owner Stan Kroenke has remained tight-lipped. In his stead, Gazidis has said the board "100% supports" Wenger.
But making matters more concerning is the break-up of the current squad.
Cesc Fabregas and Samir Nasri appear certain to leave the club, while Emmanuel Eboue, Nicklas Bendtner and Manuel Almunia could also follow already-departed Gael Clichy and Denilson out of the exit door.
"I'm sure one of the reasons [Arsenal have yet to make major moves in the transfer window] is because Wenger was waiting to see what was going to happen with Fabregas and Nasri," said Dixon.
"With those two apparently now leaving, there is work to be done [in rebuilding the squad] quickly. They need to sign a player - or players - with experience who can lead a lesser-experienced team, players they can look up to in the dressing room."
Not that Wenger should be held solely responsible for the club's transfer activity - or lack thereof - says Fynn.
"As far as the board is concerned all is well," the former consultant to the Football Association told BBC Sport. "If you look at the complete turnover of the club they are among the biggest clubs in the world.
"That is where the club want to be. Winning trophies is a bonus, but it's secondary for the board."
Still, the club's frugality in the market appears even more marked when placed in contrast to the north Londoners' rivals.
Since January of this year Arsenal have spent about £23m. Compare that to Manchester United (£53.8m), Chelsea (£100m - when Romelu Lukaku is confirmed), Manchester City (£80m) and even Liverpool (£102m).
"Arsenal are two to three players away from making that extra step," former Manchester United defender Gary Neville said this week. "They have been close and then faded away.
"They need to hang on to the players they have got or invest in new ones."
All of which leaves Wenger at something of a crossroads - abandon the style that has won plaudits but not trophies, or risk the continued frustration of the club's fans with a youth-first approach that has defined his recent years.
In a survey conducted by the Arsenal Supporters' Trust this summer, 76% of supporters are "less than satisfied" with the club's performance in recent years.
Even more worryingly for Wenger, just 40% say he should remain in charge of the club if they fail this season for the seventh successive campaign to win a trophy, while 69% believe the manager's football philosophy takes too much precedence over winning trophies.
"I think in order to win the Premier League you have to have a game plan when you don't have the ball - and I'm not sure the team is good enough in that department," added Dixon.
"There needs to be a change in mentality to work harder collectively to try and win the ball back earlier. It's not just about personnel - it's about old school coaching."
It all adds up to a time of real concern for the club.
With disillusionment growing quickly among supporters, and Gazidis himself admitting that the manager's future will ultimately be decided by the fans, Wenger has much to prove to those who believe he has lost the magic touch that brought Arsenal three league titles and four FA Cups in his first nine years of his tenure.
"The time is now for Arsenal and Wenger, they need that monkey off their back that says they've not won a trophy for so long," said Winterburn. "Already for many supporters the wait for something to fall their way has gone on too long."
A fascinating season in prospect for Wenger, then, in anyone's eyes.
Source: Sam Lyon, BBC Sport on 12 Aug 11
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