Wenger once responded to losing a Champions League semi-final first leg at Manchester United by publicly inviting a non-believing reporter to what he was convinced would be his victorious press conference after the return at The Emirates.
He even promised "a magnificent performance". He got one all right, only it came from Manchester United and two goals inside the first 11 minutes meant the invite to a triumph was torn up.
Still, Wenger's optimism has rarely wavered but he will need every ounce of the old conviction when he takes the roll-call for Arsenal's flight out for their Far East tour next weekend as he ponders the most turbulent phase of his tenure at the club.
It seems Cesc Fabregas is heading, finally, to Barcelona, while Gael Clichy is off to Manchester City and Samir Nasri may well also be Manchester-bound - although his final destination could be Old Trafford.
Andrey Arshavin is also said to be unhappy but the growing mood of disaffection with his efforts among the Emirates gallery last season suggests he would not be missed.
Losing Nasri and Fabregas would be a major blow to Arsenal's prospects - photo: Getty
Arsenal's collapse at the conclusion of last season when a pursuit of four trophies was quickly transformed a sixth campaign without success led to renewed calls for a rebuilding programme, something the stubborn Wenger finally seemed to embrace.
The problem confronting Wenger is that he is not controlling the process, it is being taken out of his hands by disaffected players.
His great skill in the past, when success came regularly, was that he was - in football terms - the consummate economist and alchemist. He was masterful at selling players at the best time and for the best price, while renewing his squad with younger replacements. For years you could barely see the join.
He now faces the most crucial weeks of his Arsenal career. Wenger must recapture that skill quickly but if he gets it wrong then he knows he risks further demonstrations of the unrest that started to surface at The Emirates towards the end of last season.
But is the situation really as chaotic as it seems? Wenger will tell you it is not.
He may even turn what looks like an exodus into an opportunity. Fabregas looked more and more like a player with his mind on Catalonia as last season progressed while the loss of Clichy, who has been in decline for two seasons, hardly represents a devastating blow.
Nasri's apparent dissatisfaction potentially represents the most damaging blow and not just because he could end up at one of Arsenal's Premier League rivals. It was a setback no-one at Arsenal appears to have seen coming until it was too late, although Wenger has not given up hope of persuading him to stay.
If Fabregas and Nasri go - Clichy is neither here nor there in my opinion despite being a fine player earlier in his Arsenal career - and Wenger's replacements are not successful right away, how long before Robin van Persie casts his eyes elsewhere or Jack Wilshere attracts serious interest for other clubs?
And how can Arsenal hope to attract the sort of players to challenge for titles at home and in Europe if their best players are effectively seen to be forming an orderly queue at the exit?
Wenger will playing for high stakes in the weeks before the season starts. If he does not bring in the right players, Arsenal will fall even further off the pace with Manchester United, Chelsea and Manchester City in various stages of rejuvenation.
However, it is not a situation without hope. If Wenger can get more than £60m for these three players - and it surely unthinkable that the club's board will not hand him the funds he has brought in - then he has the opportunity to shape a new Arsenal built around Wilshere, Van Persie and Aaron Ramsey alongside the young talent he cherishes such as goalkeeper Wojchiech Szczesny.
After all, this is not the dismantling of a successful side, it is the changing face of a team that has won nothing for six years and has proved alarmingly inadequate when presented with the greatest challenges.
Wenger's self-belief has never been shaken but now he has been presented with his greatest test. If he fails then Arsenal will fail. It is as stark as that in Arsenal's current condition.
Wenger is under the severest pressure of his Arsenal reign - photo: Getty
Despite what many Arsenal supporters believe, many of us would love to see this wonderful manager regain the sure touch of his early years and end his barren sequence.
To do so, he will also need to unearth players of steel to go alongside the silk provided by Wilshere and Ramsey. Gary Cahill of Bolton and Chris Samba of Blackburn may not appear to be identikit Wenger players but if last season finally got one message across, it was that Arsenal needed substance to go with style.
Former defender Nigel Winterburn said: "It has got to the stage where you look at the amount of money Man City have got, United have already gone out and bought players and Chelsea will spend.
"I don't think Arsenal can compete with those teams financially, but people will want to see that the squad is being strengthened because they have come up really short in terms of spending over the last two years.
"They need to get that winning mentality and that could mean signing two or three English players to get that English spirit alongside the style of football they play.
"If Arsenal don't do that, they are not going to win the league because all the other top teams will get stronger and we are not powerful enough over 38 games to compete - although they are not far away."
Everton's Phil Jagielka would be perfect for Arsenal, a defender who operates within a no-frills framework and is a voice and leader on the pitch - but this is not a deal that will find any willing takers at Goodison Park after Wenger was turned away last summer.
Lille's Gervinho is more in the Wenger mould while the Argentine Ricardo Alvarez is an exciting talent - but Wenger will need more bite in midfield to help Wilshere.
Perhaps England coach Fabio Capello has dropped him a hint by placing West Ham United's Scott Parker alongside Wilshere in the England side with some success. Age makes him a departure from Wenger's usual template and it would be a short-term fix, but long-term planning has brought nothing in the way of trophies since the FA Cup win against Manchester United in 2005 so it is surely worth consideration.
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