When Leonardo Bonucci decided to return to Juventus last summer after just one season at AC Milan, team-mate Suso admitted, "He feels he took a step back signing for us and that is why he is going back to Juventus."
Despite receiving "several offers" from elsewhere himself, the Spanish winger insisted that he was happy to stay put, buoyed by the club's acquisition of then Bianconeri forward Gonzalo Higuain.
"When the project is interesting and players like him arrive," he reasoned, "it is always positive."
However, Chelsea-bound Higuain deciding he's had enough after just six months at San Siro has done nothing but cast the club in a depressingly negative light.
Milan have signed two champions in the past 18 months. Both quickly lost faith in the "project" they were initially so keen to embrace and extol.
Of course, there were other, more emotional, factors involved in their respective departures.
Bonucci only left Juventus in the first place because of a falling out with coach Massimiliano Allegri, admitting that his decision to move to Milan – which was completed in just 48 hours – was "taken in a moment of anger".
However, neither Bonucci nor Higuain would have thrown in the towel had they been utterly convinced by Milan's ability to reclaim their place among the game's elite.
In April 2018, Bonucci publicly called for the addition of "international class players" at the end of the season. However, by that point, rumours were already rife that Milan's Chinese owners, Rossoneri Sport Investment Lux, didn't have the requisite funds to make their loan repayments.
As a result, the club fell into the hands of Elliott Management Corporation. Following the transfer of ownership to the American hedge fund, Rossoneri fans feared asset-stripping i.e. the immediate sale of the club's top players.
However, Elliott have instead elected to do something that their predecessors would not, namely manage the Rossoneri in a sensible and shrewd fashion.
Bonucci was allowed to return "home" but Milan secured the services of the promising young centre-half Mattia Caldara in return, while they also snapped up Higuain on loan for €18 million with a view to a permanent transfer at the end of the 2018-19 campaign.
However, with Higuain now on his way to Stamford Bridge, Milan's hopes of securing a return to the Champions League have taken a major hit.
Granted, they are only two points behind fourth-placed Roma in the Serie A standings with a game in hand, at Genoa on Monday, but the December 29 victory over SPAL just before the winter break represented a first in five games for Gennaro Gattuso's men.
Higuain scored the winner that day and declared afterwards, "I came to Milan because I was convinced by the project here and I want to continue like this. Now we've got the Supercoppa; it's the first trophy of the season and we want to win."
Milan didn't win, though, beaten by a solitary strike from Cristiano Ronaldo on Wednesday evening, and Higuain didn't even start. The party line was that he was suffering from a fever but he appeared in the second half as the Rossoneri tried to turn the game around.
In reality, he began on the bench because it was already clear that he was heading for the exit door, with Milan hoping to replace him with Krzysztof Piatek.
It could well prove an inspired move on Milan's part: the Pole may have been a virtual unknown six months ago but the 23-year-old has taken Serie A by storm this season, netting 13 goals since joining Genoa last summer.
However, the Rossoneri's ability to hold on to their last two statement signings offers a painful reminder for the fans that there will be no swift solution to the financial problems left behind by the previous owners, who spent €233 million on new players in the summer of 2017 yet were forced to hand over control to Elliott last year.
In addition, the appointment of Ivan Gazidis as chief executive has been greeted with understandable caution. He is credited with doing stellar work from a commercial perspective at his former club but Arsenal went backwards in a sporting sense during his decade at the Emirates.
The Gunners lost a host of top players while he was at the helm – usually at knockdown prices because their contracts had been carelessly allowed to wind down – and his Emirates legacy is a grossly inflated wage bill that is presently preventing the club from doing any permanent deals during the current transfer window.
On the plus side, the new Milan administration features former players with the club's best interests at heart, chief among them director general Leonardo, a charismatic and intelligent individual with a proven track record when it comes to attracting top talent, most notably at Paris Saint-Germain.
The addition of Paolo Maldini to the team as sporting strategy and development director also bodes well, given the defensive icon turned down a plethora of previous offers to rejoin the club in an administerial role because he was unconvinced by the financial and sporting viability of the projects overseen first by Barbara Berlusconi – daughter of former owner Silvio – and then Li Yonghong.
"The beautiful thing about today is that we now have myself, Paolo and Gennaro in the sporting sector of the club," Leonardo enthused at the start of the season.
Still, the Brazilian has repeatedly stated that due to the excesses of the recent past, he and his former team-mates and current colleagues remain financially hamstrung.
"Unfortunately, we have to deal with Financial Fair Play (FFP)," he recently explained. "Everyone knows this, so, January will be a window not of major deals but opportunities. There will be exits so that there will be arrivals.
"Nowadays, one has to work the market with the FFP manual in hand. But if this Milan finishes fourth, then we will have a major window in June.
"However, if the club's goals are not met, there will be no major signings and the current players on big deals will not be retained.
"But, sooner or later, we will get where we want to go."
Obviously, Milan's fans, so accustomed success, are growing impatient but there is no quick fix to the mess left behind by Li & Co.
The prospect of the seven-time European champions once again stockpiling superstars remains a long way off.
Indeed, as the losses of Bonucci and Higuain have shown, just keeping a hold of their best players is proving difficult enough for Milan right now.