MEN AGAINST BOYS (2006-2013)
Wenger loved Highbury. But moving to the Emirates always felt, to him, imperative for the club to push forward.
When Arsenal decided to leave their ancestral home and prepare for a move that would cost around £400million (S$708 million), he knew and accepted that for a time it would compromise his team.
What he did not know was that all Arsenal's plans would be thrown by the impact of oligarchs and billionaires landing suddenly to transform the football landscape.
Arsenal's belt-tightening coincided with lavish spending elsewhere.
"You feel like you have stones against machine guns," Wenger said. "People don't want to know that. They just want you to win the championship."
That period turned out to be more challenging than the club ever anticipated.
Wenger's plan to sail the choppy waters with a modestly priced boat compared to the Premier League's financial powerhouses was to pin his faith in youth.
The idea was brave: find the best young players you can, inculcate them with some club spirit and develop a team who grow together and feel loyalty to one another and the cause.
It nearly worked. Cesc Fabregas in his youth was sensational. In the group that included Robin van Persie, Samir Nasri and Abou Diaby, Wenger was sure he had enough talent to compete.
But project youth eventually crumbled. The damage when Fabregas and Nasri left, followed by van Persie, was felt keenly.
Wenger felt a very personal sense of loss. The ideology he believed in collapsed around him. "You cannot pretend you are a big club," he said.
Rightly or wrongly Wenger always felt if a player wanted to go, it was time to let him go.
The vulnerabilities in his team during these moments made it so tough to compete with the best around.
A SECOND COMING (2014-15)
Several times during his Arsenal tenure Wenger could have left for other clubs. He never did. He stayed put, earning a handsome salary but also absorbing the flak.
Why? Because he started the project to see Arsenal over their expensive move, and he wanted to finish it.
After winning the FA Cup in 2005, Wenger endured moments of immense pressure and blame.
The 8-2 defeat at United was deeply humiliating. There were a cluster of those calamities in recent seasons, piercingly bad defeats that allowed Jose Mourinho to deliver that cutting "Specialist in Failure" line.
"The immense importance of football is sometimes scary," Wenger said. "When you don't win you are responsible for so many unhappy people. Sometimes it's better not to think about it because it could damage your life too much."
Set against that analysis, it was meaningful when Wenger finally experienced the relief of winning again.
The FA Cup final in 2014 against Hull City was a roller coaster. Going 2-0 down was, he said, "surreal" as the thought of losing when carrying so much expectation was unthinkable.
Arsenal rallied and won the Cup in extra time.
"Winning was an important moment in the life of the team," Wenger said. "We had such a feeling of relief and happiness."
The following year they retained the trophy with a swashbuckling performance. The graph was back on an upward curve.
Silverware, and the ability to attract a higher calibre of player - like Mesut Ozil or Alexis Sanchez - made a difference.
Wenger felt bullish again.
THE GREAT SURVIVOR (2015-16)
Wenger has had to roll with some heavyweight punches but has never got close to stepping out of the ring. What keeps him there is the feeling in his gut that keeps him obsessed by trying to win.
"I can only survive if I have that desire to win," he explained. "If you only fight to win that means you have to forget your life first and foremost."
Whatever his critics make of him, he retains the full support of his club's majority owner, Stan Kroenke, and the board.
In Arsenal's broader diaspora there is black, white and every shade of grey whenever there is discussion about Wenger's ways.
Some supporters frustrated by the ratio between high ticket prices and club honours vent their spleen and hold up banners.
Others feel a sense of loyalty and affection for a man who has given a lot of himself to the club during his tenure.
Many are stuck in the middle.
Wenger often appears reserved in front of the post-match TV camera. What the majority do not see is the personal side of Wenger, and the qualities that have kept him in the same job for so long.
His keen intellect, his sense of trust in those around him (sometimes arguably too much trust), his dedication and his humour all make the man.
He is very funny and has no problems laughing at himself.
"He is such a clever man with such a knack at understanding people. But he could also be a walking disaster," said Ray Parlour. "He would do something accidentally every day."
He could get tangled up in the nets, drop the pudding off his plate without noticing or join in a squad relaxation technique but lie with his legs up against a partition wall rather than a solid one and roll straight through it.
THE FUTURE (2016-?)
After 20 years there is no single perception of Wenger and his time.
We look today at the tall, wiry frame, sometimes bearing that strained expression when things are not going well, at others more urbane, with a ready wry smile and dry one-liner.
In the current era of incessant managerial scrutiny, the pressure is relentless.
But rest assured he goes home knowing that the biggest critic, the force who applies the harshest pressure, is the man in the mirror.
His current deal expires at the end of this season and, as with all his other contracts, the only person who will decide if he signs another, walks away, moves upstairs or tries something completely different is him.
It is, as he says, the club of his life.
"What I like about Arsenal, and I am very proud of, is that the club is a mixture of respecting traditional values while not being scared to move forward," he said.
"I believe in the last 15 to 20 years you have all of that - fantastic periods, difficult periods - I stayed here for the respect I have for all that."
Whatever happens and whenever it happens to end this collaboration between manager and club, Wenger is the last of his kind.
The average time span for a manager in England's professional game is currently 13 months. We will not see a 20-year manager at elite level again.
THE GUARDIAN