At an especially heated Questions & Answers session with then-Arsenal chief executive Ivan Gazidis in June 2017, an elderly supporter who claimed to have missed five games in the preceding 50 years confessed that the atmosphere at his beloved club was "the worst I've ever known".
"Something is wrong," he lamented. "We appear to be in a mire and unless we get active, I can only see things getting worse."
He was right, too. And Gazidis must have known it. Because he left the Emirates the following year, after Arsenal had finished sixth in the Premier League – their worst placing since 1995.
Unsurprisingly, it is difficult to find a Gunners fan with nice things to say about Gazidis.
Indeed, legendary striker Ian Wright spoke for many last year when he referred to the former chief executive as "a fool" who had "a lot to answer for" in relation to the club's dramatic decline during his nine years in north London.
It is curious, then, that Gordon Singer is a big Arsenal fan because it was he who personally picked Gazidis to become AC Milan CEO in September 2018 (though he wouldn't take up his role until December of the same year).
After all, Gazidis was walking away from a mess of his own making at the Emirates – yet he was entrusted with the responsibility of cleaning one up at San Siro.
When his appointment was confirmed, Milan’s official website proudly informed fans that they had acquired the services of "a world-class football executive with a track record of sporting and commercial success across the globe".
Most Gunners fans would have strongly disagreed, and perhaps even laughed at the claim that "Under Mr. Gazidis’s leadership, London-based Arsenal Football Club enjoyed both on-field success and off-field prosperity."
The reality is that Arsenal regressed horribly during his tenure, both in a sporting and commercial sense, as underlined by the fact that over the past decade they have dropped from fifth to 11th – their lowest position since 2001 – in the Deloitte Football Money League.
When Gazidis took over, Arsenal had been in the Champions League final just two-and-a-half years previously; now, they haven't played in Europe's premier cup competition since 2016-17.
The loss of revenue has had a disastrous knock-on effect on the club's standing within the English game, not least because it was exacerbated by the tying down of Mesut Ozil to a ludicrously high wage, and the loss of valuable assets such as Alexis Sanchez, as part of a swap deal with Henrikh Mkhitaryan, and Aaron Ramsey, on a free transfer, because they weren’t sold or persuaded to sign extensions before their contracts entered their final years.
This was Gazidis' true legacy at Arsenal and they are still paying the price.
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And yet Singer felt this was the man to revive Milan, who had fallen into the hands of Singer's father Paul, the founder of the Elliott Management Corporation, the American hedge fund that assumed control of AC Milan in July 2018 after Chinese businessman Li Younghong proved unable to repay his debts.
Elliott and Gazidis initially put their faith in three former Milan players to get the club back into the Champions League: Leonardo (sporting director), Paolo Maldini (sporting strategy & development director), and Gennaro Gattuso (head coach).
Despite doubts over Maldini's future, he was actually promoted to technical director last summer before being joined at San Siro by another former team-mate, Zvonimir Boban, who had been working for FIFA.
Maldini and Boban were essentially charged with looking after the sporting side of things and their most significant act ahead of the current season was hiring Marco Giampaolo as coach.
Embarrassingly, the pair decided to sack the former Sampdoria coach after just seven games – and they have been on borrowed time ever since.
Giampaolo's successor Stefano Pioli has done a decent job steadying the ship – they are now up to seventh in the Serie A standings, three points behind sixth-placed Napoli with a game in hand – while the January return of former crowd favourite Zlatan Ibrahimovic lifted the whole atmosphere around the club.
However, Pioli's reign was always likely to end at the end of this season and selecting the right replacement was the most important call to be made at Milan this year.
Boban, then, was furious when he learned that Gazidis had already made the decision to turn to Ralf Rangnick without consulting him. Or Maldini.
Never one to hide his feelings, the former Croatia international went public with his frustration in an interview with the Gazzetta dello Sport last Friday.
"Until a few days ago, I didn't think it were true that there were two souls within Milan, albeit taking into account all the thousand initial difficulties, cultural differences and very different passions for the Rossoneri cause," Boban lamented.
"The fact we're having to talk about this is not good for anyone. The worst part is that this destabilising event is happening during a moment when the team is improving and you can see Stefano Pioli's hard work.
"Not even warning us was disrespectful and inelegant. It was not the Milan style. At least not what we remembered the Milan style as being.
"We've already talked to Gazidis. For the good of Milan, it is certainly necessary that a meeting with the ownership happens as soon as possible."
There will be no conciliatory talks though, just negotiations over severance packages.
Boban is out, and Maldini will be soon. All that's left is the official confirmation.
Given their popularity with the fans, there will obviously be a backlash in the stands, but there could also be dissent in the dressing room.
Boban played a pivotal role in Ibrahimovic’s decision to re-sign for Milan, while it was Maldini who persuaded Theo Hernandez – one of the big success stories of a trying season at San Siro – to take a pay cut to join the Rossoneri last summer.
The two directors could, thus, argue that while Giampaolo was a disaster, they have done well in the transfer market, and with very little money to work with given the financial difficulties which prompted Milan to accept a ban from competing in the Europa League this season in the hope of balancing the books in time for the next Champions League campaign, whenever that may be.
As Boban pointed out in the Gazzetta, "At this moment, despite the efforts we made in the January transfer window, making many cuts and sales to lower the wage bill, we still don't know what margins we'll be working with for the summer.
"We were asked to lower the average age of the squad and we did that, but always maintaining the need for the right mix between youth and experience. The January transfer window shows we were right, you can see how quickly the younger players improved with more senior figures by their side.
"But owners must be clear both in terms of the budget and their objectives. In essence, we must respect the needs of the club to balance the books, while the owners must respect leaving the sporting results to those who represent the history and values of a great club.”
Clearly, it was Gazidis’ perceived interference in the sporting side of the business which most vexed Boban, who has not lacked support for going public with his indignation.
“Gazidis went to talk to this other coach when it wasn’t his job,” former Italy international Christian Vieri told Tiki Taka on Monday night. “Who even is Gazidis? What does he do at Milan? Boban and Maldini are meant to have that role.
“Boban couldn’t just shut up and take it. You need guts in life, to be a real man, and Boban is that. I wouldn’t say he was fired.
“What happened is that [Gazidis] was cowardly and went behind his back, and [Boban] is not a puppet. He has character and says things to your face.”
The Curva Sud ultras, though, are disgusted that all of this is playing out in public, releasing a statement on Wednesday saying all of the sniping – even former director Massimiliano Mirabelli has got involved by attacking Maldini – has underlined the importance of "washing your dirty linen in private", arguing that the whole affair has only further disillusioned fans that were "already on the edge".
The ultras also pointed out that while Boban and Maldini have made mistakes, starting over and effectively having a "year zero" every summer is not doing their beloved club any good.
The bottom line, though, is that Gazidis has always had the full support of Elliott and had been pondering such a radical shake-up since last summer.
Indeed, he believes that the cash-strapped club would be best served by focusing exclusively on young players, which is why he considered hiring Lille sporting director Luis Campos before Boban's arrival.
Now, he has decided to not just gamble on Rangnick, but go all-in, with the latest reports suggesting that the German will be given an unprecedented level of control over the sporting side of the club, essentially serving as coach, technical director and chief scout.
It's an interesting move from Gazidis, given he sought – successfully – to take away that level of control from Arsene Wenger towards the end of their time together at Arsenal.
Now he is set to give Rangnick – who has an admittedly excellent track record at developing young talent – free rein at San Siro.
Milan has a proud history but he has decided to effectively cut all ties with the past in order to focus on the future.
Given he had the backing of Singer, this was a civil war he was always going to win.
What he needs now, though, is to ensure that the Rangnick revolution is a success.
Otherwise, he'll be fielding more uncomfortable questions from long-suffering supporters in no time at all.