The decision has been staring Arsene Wenger in the face for years but that only made it more difficult to take.
It was around this time last year that the Frenchman sought solace in regular walks with former vice-chairman David Dein and his dog somewhere near his Totteridge home as he weighed up whether to sign a new contract.
His press conferences had become an object lesson in obfuscation: he wanted to stay; he might manage somewhere else; he didn’t know what to do; he did know, but he wasn’t telling. It wasn’t deliberate. All of it was racing through his mind.
For the first time, the board had become split over the iconic manager’s fate. Ultimately, Wenger convinced majority shareholder Stan Kroenke he was worthy of one final crack in restoring Arsenal to former glories - glories which he had created - and a two-year deal was agreed.
Wenger internalises everything. It is the root of what makes him such an engaging interviewee on any topic you care to mention. Over the last 12 years of covering the club, I’ve seen first-hand Wenger offer genuinely revealing and heartfelt insight into everything from Brexit to David Bowie.
“The message he gave to my generation was very important because it was after the Second World War and it was basically - be strong enough to be yourself,” said Wenger of Bowie. “That is a very strong message and very important for my generation.”
It is a message Wenger thoroughly heeded. He is his own man, a revolutionary whose principles and ideals were uncompromised even in this current age of lavish spending and short-termism.
Wenger may not always have been right but he did everything in the right way. He cares about developing footballers as human beings, touching their lives in a manner that lasts forever. It is why former players return to train, take their coaching badges and revel in the enduring warmth.
Wenger won the ‘Outstanding Contribution to London Football’ prize at the 2015 London Football Awards, of which I’m a judging panel member, and shuffled around his calendar to attend the function at Battersea Revolution.
He stayed to exchange stories with Willow Foundation founder Bob Wilson and sign autographs for fans before speaking with me at London Colney the next morning to discuss how the night had gone and how much money had been raised.
Privately, Wenger was always warm and engaging. After England drew 0-0 with Algeria in Cape Town at the 2010 World Cup in South Africa, I caught Wenger’s eye in the press seats as he paused between broadcasts for French television. I pointed to the pitch in disbelief at the dire performance England had produced. He shook his head in response before mouthing across the words: “I’m sorry for you!”
It became difficult to scrutinise and criticise such an affable, intelligent manager able to converse in six different languages, but results increasingly demanded it.
Over time, he became arguably more revered overseas than in England; just last week, Russian journalists mobbed Wenger for pictures in the wake of Arsenal’s 2-2 draw with CSKA Moscow.
Yet even under mounting pressure over the last few years, he never hid. He rarely lost his temper, too. There were a few occasions when he flared up – usually when incorrect information appeared in the public domain – and his press conferences have, generally speaking, got shorter in recent seasons.
Yet he stood by, and defended, his actions. Players were protected. So were the board. I’ve been present at several Annual General Meetings where Wenger disarmed a hitherto toxic environment with an engaging speech mixing honesty, compassion and class.
Kroenke and Ivan Gazidis are able to adopt a laconic approach to the press because Wenger is so forthcoming.
But, ultimately, he ran out of answers. Recent media interactions have been evasive over his future, at a loss to explain the team’s underperformance. Empty seats and fan protests - apathy and anger - affected him. It will have been a painful conclusion to reach, but the modern-day failures were severely threatening to outweigh past successes.
Wenger was facing an end-of-season review into his position that would not have been favourable and he took perhaps the last opportunity to determine the timing of his own departure.
Informal talks have been going on for several months over his future. This newspaper first revealed in January there was a strong possibility he could leave, and the clarity after months of speculation will at least provide some calm.
He will hate what now follows. Amid all our sepia-toned reflections on the past, Wenger will be invited to select his own highlights. Yet he is not one for retrospection.
He does not display medals or accolades at his house - he often gives them away to members of staff. It has been a while since Wenger won a ‘Manager of the Month’ award but he has donated the last few to be auctioned for charity.
Wenger looks inwards and then forwards. It is his way. It made him an Arsenal legend.