The loss of Thiago Silva and Zlatan Ibrahimovic in addition to the majority of their ageing heroes (one of whom, Filippo Inzaghi, retired on Tuesday) means this is perhaps the first time in decades that AC Milan lack an inarguably world-class star, the sort that all of Europe's top clubs are chasing.
Supporters are furious, so much so that the club have decided to offer season-ticket refunds to calm the anger, they were shown up by main rivals Juventus and Inter in Saturday's Trofeo TIM and they don't really have the financial might at present to invest heavily in someone to set pulses racing.
The last time that they completed a sale as high-profile as Silva and Ibrahimovic's was in 2009 when Kaka joined Real Madrid for a reported £56 million in what was briefly a pound-sterling world transfer record.
That move hasn't worked out anywhere near as well as the Brazilian would have hoped. The 30-year-old has only made 49 La Liga starts in three seasons. Injuries initially limited his opportunities, however over the last two years, he has been a clear second choice to Mesut Ozil.
A new low might have been reached this week as the former Ballon d'Or winner was told that he wasn't even required to travel for the Spanish champions' friendly with Real Oviedo, with assistant Aitor Karanka making it fairly clear that they are open to selling him.
The consensus is that in doing so, it creates a space for Luka Modric, but that represents far from a like-for-like switch, as the Croatian tends to operate deeper in the kind of areas patrolled by Sami Khedira and Xabi Alonso.
As Kaka experienced one of the worst moments of a testing spell at the Bernabeu, his agent Gaetano Paolillo was out for a bite to eat with AC Milan vice-president Adriano Galliani, sparking rumours of a return to the home of his greatest successes.
Galliani did little to stop the speculation, stating rather unambiguously: "Some loves never die, they just go round on a long journey and come back again." The Rossoneri are 2.65 to top Serie A and are 38.037/1 to win the Champions League.