Arsenal's chief executive Gazidis continues to be linked with the Rossoneri, and his departure is something the Gunners are already preparing for, after the 53-year-old made the club's board aware of an offer.
Wilson noted Gazidis won't be moving on within a month, since any "potential notice period at Arsenal would rule out that sort of timescale and there is confidence that he would not push to leave suddenly and risk a damaging void."
Reports from Italy had suggested he would be in place in Milan within that timeframe:
The Gunners are said to be confident they could quickly replace Gazidis should he move on, although there is hope at board level he will resist any offer to leave. Even so, the lure of Milan can't be overlooked after American hedge fund Elliot Management assumed control of the club from Li Yonghong recently.
Gazidis has a history with Elliot Management boss Paul Singer, according to Wilson.
For many, the timing of Gazidis' departure would be strange after he was credited with overhauling the management structure at Arsenal. He oversaw and prepared for the end of Arsene Wenger's near 22-year tenure by adding new decision-makers at the club.
While Wenger famously controlled most, if not all, aspects of Arsenal's sporting operation, Gazidis appointed Sven Mislintat from Borussia Dortmund to be head of recruitment. His attempts to sign players are aided by Raul Sanllehi, the Gunners' head of football relations, who was brought to north London from Barcelona by Gazidis.
He also led the process to appoint Wenger's successor, former Sevilla and Paris Saint-Germain boss Unai Emery.
Walking away from a new era he has helped manufacture from the ground up would be curious:
Others think moving to Italy would represent a step down for the man who is now Arsenal's senior powerbroker in the post-Wenger landscape:
As much as AC Milan are a huge club I never understood why Ivan Gazidis would want to leave Arsenal after becoming kingmaker following years of battling to reach the position. Arsenal is his kingdom now. To move anywhere else would be a step down, certainly in terms of influence https://t.co/WigvZQUydX
Gazidis leaving would no doubt catch Arsenal by surprise, with chairman Sir Chips Keswick recently feeling confident enough to call the CEO "fully committed" in a statement on the club's official website.
Emery also expressed a belief Gazidis is in it for the long haul as the two work to reshape an Arsenal squad which struggled to a sixth-place finish in the Premier League last season:
For all the talk of Gazidis being wrong to walk away from Arsenal, the issue may be deeper than simply assuming he wouldn't give up control he seemingly wrestled from Wenger's grasp.
By contrast, Wilson noted how "there is a sense inside Arsenal that Gazidis may now feel that the time is right for a different challenge."
While many are content to credit Gazidis with sparking an apparent long-overdue revolution, not everybody rates his work.
Among his detractors, former Arsenal midfielder Stewart Robson told talkSport's Jim White (h/t TalkSport.com's Joe Moore): "When he came to Arsenal I knew a very high-profile sports agent, who told me he was ‘the worst negotiator’ he had ever dealt with. Basically, he didn’t know his stuff."
Robson, a fierce critic of Wenger, also took Gazidis to task for not sacking the Frenchman "many, many years ago."
If Gazidis does move on, only positive results on the pitch will determine whether the moves he made to offset Wenger stepping down left the club in good health. Without improvement, his walking away will be seen as one more sign of a club hindered by a muddled strategy at the top for too long.