The Frenchman enjoyed plenty of highs during his time in north London, but admits that he probably should have looked to take on another challenge.
Arsene Wenger concedes that spending 22 years in charge of Arsenal was a mistake, with the Frenchman feeling as though he became “a prisoner of my own challenges”.
Having worked so hard to rebuild the Gunners in his image, the long-serving coach found it difficult to sever ties with the club.
There were plenty of opportunities for him to walk away, with Real Madrid and England having made several attempts to secure the services of a proven performer.
Wenger also faced fan protests towards the end of his reign, but he eventually departed on his own terms at the end of the 2017-18 season.
The 68-year-old admits that he should have probably made a fresh start some time ago, rather than clinging on in north London, but his passion for a high-profile job kept him coming back for more.
Wenger told RTL when asked to pick out the biggest mistake of his career: “Perhaps staying at the same club for 22 years.
“I’m someone who likes to move around a lot, but I also like a challenge. I’ve been a prisoner of my own challenge at times.”
Wenger guided Arsenal to three Premier League titles, with his iconic ‘Invincibles’ side of 2003-04 negotiating an entire English top-flight campaign unbeaten.
He also reached the 2006 Champions League final, but saw European dreams crumble as a succession of last-16 exits were followed by two finishes outside of the top four in England.
FA Cup success helped to paper over the cracks at times, with Wenger leaving north London with seven winners’ medals from that competition.
He is yet to take on a new role ahead of the 2018-19 campaign, with the latest reports suggesting that a man who left Nagoya Grampus Eight to take the reins at Arsenal in 1996 could soon be heading back to Japan.