Why Sunday's match could prove a turning point in Wenger’s bid to return to the top

It was the most harrowing of setbacks, the sort that can send a career spiralling out of control. It did not blunt Arsene Wenger’s eloquence. “You do not compare your pain,” he said, with the air of a man who was hurting deeply.

The French revolutionary, the modernist manager who had challenged Sir Alex Ferguson’s seemingly ancien regime for supremacy in England, had been vanquished by his bitterest foe. Manchester United 8 Arsenal 2, August 2011. Wenger recognised the magnitude of the scoreline – Arsenal’s heaviest defeat for 115 years – was such that he should not plead mitigating circumstances. Ferguson, perhaps recalling his own lowest point, was unusually sympathetic towards his victim.

Not for the first time, the conqueror was a role model. Ferguson’s own greatness was cemented before the nadir that prompted thoughts he was a fading force, but it was embellished by his renaissance after the awful autumn of 2005. The 4-1 defeat at Middlesbrough was a shambolic showing. It brought the end of Roy Keane’s punditry career with MUTV, not to mention his footballing time in a United shirt. It proved a symbolic moment, the end of an era; just not Ferguson’s era. He won a further five league titles and a second Champions League.

Bill Shankly, too, used an embarrassment as a catalyst for renewal. The 1970 FA Cup defeat to an unheralded Watford side prompted the break-up of Shankly’s first outstanding Liverpool side. It brought an exercise in ruthlessness: Tommy Lawrence, Ron Yeats, Roger Hunt and Ian St John were consigned to Anfield history. Shankly was not. Like Ferguson, he retired a winner, securing the league title, the FA Cup and the UEFA Cup in his final two seasons.

Theirs were epic tales, enriched by their final acts. They amounted to the rise, fall and rise again of managerial marvels. Like Shankly and Ferguson, Wenger has been a transformative figure who has rebranded a club with his ethos, his efforts and his extended service. What would secure him a position alongside the great Scots is a similar return to the summit of the game. At 65, with two years left on his contract, this may be the optimum opportunity.

Wenger has won successive FA Cups in his partial rehabilitation but not the biggest prizes. It has proved slower than Ferguson’s; barely 18 months after the humiliation on Teesside, he had regained the Premier League. It has been built on different principles, too. Ferguson shifted the emphasis in his team to youth, to the generation of Wayne Rooney and Cristiano Ronaldo. Wenger responded to his hammering at Old Trafford by importing experience, in Per Mertesacker and Mikel Arteta (and, less usefully, Andre Santos). They paved the way for Petr Cech’s signing. Those frantic few days in August 2011 marked the start of a shift in policy, a recognition that teams with too many youngsters can be too naïve and that sometimes it pays to spend on players with a diminishing resale value.

Despite the annual top-four finishes, progress has not always been smooth since then. The greats deserve more leeway than the mere mortals of management, but it has not always been granted to Wenger, especially by the supporters who barracked him at Stoke station last year. Familiar failings can undermine Arsenal: even when they develop the nous to win away at both Manchester clubs, their propensity to exit the Champions League in the last 16 lingers, as a mediocre Monaco side can testify.

Groundhog seasons have started to show some differences, in rewards and reactions. The 2014 FA Cup, ending the nine-year trophy drought, was celebrated jubilantly. Wenger greeted the 2015 triumph with a purposeful walk on the Wembley turf, his body language suggesting it was business as usual to secure silverware.

Sunday’s return to the national stadium has a significance that stretches beyond the precedents. None of the four previous Community Shield winners have gone on to become champions but this is far more of a pointer than the Barclays Asia Trophy or the Emirates Cup, both of which Arsenal ‘won’. Wenger has never beaten Jose Mourinho in 13 meetings stretching back over 11 years. If Arsenal do not overcome Chelsea over 90 minutes at some stage this season, it is harder to see them outperforming them over 38 games.

Wenger’s reign can be divided into two halves: before Mourinho and after Mourinho. Any ageing manager’s challenges include illustrating he is no anachronism by defeating his younger rivals. Ferguson did that in 2006-07 when Mourinho, 21 years his junior, had earned back-to-back titles in the previous two seasons. Shankly reclaimed the league in 1972-73 when Brian Clough, born the best part of 22 years after him, had piloted Derby to glory 12 months earlier.

The generation game can provide the grand, sweeping narrative of the sort that, like Wenger himself, is becoming an endangered species. The Premier League’s constants and colossuses have been thinned out in recent seasons by retirements and relocations; it has been farewell to Ferguson, Paul Scholes, Ryan Giggs, Rio Ferdinand, Robin van Persie, Didier Drogba, Frank Lampard, Jamie Carragher and Steven Gerrard.

The Liverpool captain offers the most recent and unfortunate proof that longevity and legendary status do not guarantee a happy ending. He went out with a 6-1 defeat. Wenger has recovered from his 8-2 thrashing in a way a lesser manager and character would not have done but the crowning glory in his revival would be to emulate Ferguson and Shankly, to show incomparable pain can bring a comparable resurgence.