Arsenal became the embodiment of his considered, cultured, quick-thinking mind, and won three titles between 1998 and 2004 playing a brand of football that drew plaudits from every corner of the country.
In 1998 Wenger's dynamic team produced a quite devastating run to the finish line to deny Ferguson's all-powerful Manchester United a third straight title. It was a statement of intent from Arsenal, and it ignited a rivalry between Ferguson and Wenger that burns bright to this day.
Ferguson struck back with a Treble the following season, but it could have been very different had Dennis Bergkamp's penalty gone in at the end of Arsenal's FA Cup semi-final replay against United. It's often argued that Arsenal would have won a second straight Double but for Peter Schmeichel.
A second Double for Wenger did arrive in the 2001-02 season, and the 2003-04 campaign will be remembered for his team of Invicibles - who went through all 38 league games unbeaten. It should have been a launching pad for a decade of success, but Arsenal have conspired to win just one FA Cup since. It's been six years since their last major trophy and Wenger's position is looking increasingly precarious.
He remains the game's great philopsher, but his philosphies are beginning to wear thin on the supporters who've watched a good number of their best players take their ambition elsewhere in recent seasons. Cesc Fabregas is the latest; Samir Nasri will follow him out the door in the next few days, Gael Clichy left earlier this summer. These are three players in the prime of their careers, playing in a fantastic stadium before crowds to match anything in Europe. They're also living in one of the most desirable cities on the planet, but that hasn't stopped them looking elsewhere to further their careers.
Arsenal fans must wonder who'll be next - Robin van Persie? Jack Wilshere maybe? You wouldn't bank on either being at The Emirates in two years' time, yet still the club and their manager tread softly in the transfer market. They could have signed Vincent Kompany. They could have signed Phil Jagielka. They could have signed Gary Cahill. Each time it appears Wenger and the club have refused to match an asking price.
It's an admirable stance on inflated transfer fees, but are Arsenal ultimately operating a false economy here? Based on their current squad Wenger has little chance of making a serious push for the title. And as each season passes so the club becomes a less appealing destination for new players.
Time and again we're reminded that the Arsenal business model is a rare success story, but eventually the lack of success on the field is going to force their hand in the transfer market - especially if they fail to secure a Champions League spot for next season. Udinese could yet deny them a spot in the competition proper this time around. Wenger said yesterday he'd be prepared to spend £40 million on "the right players", but we're beginning to wonder if such players actually exist. Moreover, unless the groundwork is already in place it's going to be difficult to push through a major deal before the window closes anyway.
There's no question stubborness is playing its part here. With each season Wenger grows increasingly desperate to prove he can win the Premier League without spending fortunes and paying out ridiculous wages. To do it just once would prove his point. But each season his team gets weaker. And each season the fans grow more impatient. You get the feeling it's now or never for Wenger and the question is whether he's prepared to sacrifice his philosophies for the sake of his job.