Arsene Wenger was ahead of his time when he arrived at Arsenal in 1996, but he leaves, almost 22 years later, out of time and out of step with the game he helped to transform during the first half of his reign as manager.
So the Frenchman's announcement of his decision to step down at the end of the season, halfway through the two-year contract he signed last summer, is a bittersweet moment for Wenger and Arsenal.
To suggest that now is the right time for change at the Emirates would be to overlook the reality that that time actually came perhaps four or five years ago.
It is a harsh assessment of the final years of Wenger's spell in charge considering he has won three FA Cups in the last four seasons, but the Arsenal that Wenger built into the most formidable team in English football was about more than winning FA Cups.
It was a team that ended Manchester United's lengthy dominance of the domestic game; an outfit which blended flair and steel, determination and the breathtaking brilliance of Thierry Henry, Robert Pires and Dennis Bergkamp.
That Arsenal team made waves, but the one Wenger leaves behind has been treading water for too long and change is overdue.
Deep down, it is difficult to imagine that Wenger does not know this too.
The 68-year-old is one of the most driven men in football, a winner to the core, and he will surely have looked at his current side with dismay when compared to his previous teams.
Yes, he was the architect of both good and bad, but the qualities which made the 1998 Double winners and 2004 "Invincibles" stand out from the pack have been absent from his Arsenal squads for the best part of a decade.
The financial burden of the move to the Emirates in 2006, combined with the game-changing takeovers at Chelsea and Manchester City, conspired to weaken Arsenal at a time when financial power became the primary ingredient of the best teams.
Prior to the arrival on the scene of Roman Abramovich and Sheikh Mansour bin Zayed al Nahyan, Wenger's ability to manage, spot talent and build great teams without breaking the bank saw him become the most direct threat to Sir Alex Ferguson's standing as the greatest manager in the game.
Former United chief executive Martin Edwards revealed earlier this year he had identified Wenger, and spoken to him, as the ideal successor to Ferguson when the Scot originally announced his decision to step down in 2002.
Wenger rejected United's advances and stayed at Arsenal to build the Invincibles, but it underlines his early achievements at Arsenal that he was the first choice to succeed Ferguson at Old Trafford back then.
The rivalry between Wenger and Ferguson in the late 1990s and early 2000s was so hard-fought and acrimonious that it defines both of them.
They built fiercely competitive teams -- which remain arguably the best the Premier League has ever produced -- but while Ferguson timed his United exit to perfection in 2013 after guiding the club to a 20th league title, Wenger stayed on too long.
Ferguson left United wanting more, and the five years since his departure have shown just how much he has been missed, but Wenger will leave with many Arsenal supporters celebrating his decision to step down.
In time, the fondness and respect he has earned will return, but as of now, his failure to move with the times and keep Arsenal competitive has tarnished his legacy.
United fans still mourn Ferguson's departure, but the emotion of the Arsenal supporters is different and that is a great shame for a man who will go down as the club's greatest manager.
His request within his statement, which urges "our fans to stand behind the team and finish on a high," is a pointer towards the dissatisfaction in the stands at the Emirates.
But perhaps by going public now with his decision to leave, Wenger can inspire a successful end to his reign -- something befitting a man who has turned Arsenal into one of Europe's super clubs.
They have a tough Europa League semifinal looming against Atletico Madrid, but with the final in Lyon next month, it would be the perfect end for Wenger to lift a major European trophy in France and hand his successor a passport back into the Champions League.
If the football gods are smiling on Wenger -- and they don't seem to have been in recent years -- they will allow him to leave next month with the Europa League trophy as a leaving present.