When Clarence Seedorf arrived as coach back in January, there was a sense of relief and calm around the club as a new cycle was ready to begin. However, things haven't worked out as planned for the Dutchman despite improvements on the pitch, as speculation, controversy and general confusion continues to engulf the Rossoneri.
- Report: De Maio agent claims Milan interest
Both expectations and objectives were managed as the inexperienced club icon took his first role in coaching, yet somewhere along the way the tranquility he had hoped to instil was disturbed. Talk of qualification for the Europa League became more imperative, while reports continue to suggest that Silvio Berlusconi is looking for investment.
However, the club owner dismissed those stories as "fantasies of others" this week, but unfortunately for Seedorf, the club hasn't been quite as forthcoming in publicly supporting him and reassuring him that his job is safe moving forward.
In the meantime, former player Pippo Inzaghi has reflected on the "great rapport" that he shares with both Berlusconi and Adriano Galliani, while Seedorf has perhaps done himself no favours by holding an interview with Sky that wasn't authorised by the club.
Galliani moved quickly to quiet further talk of a rift by insisting that the story ends immediately, but inevitably from the outside looking in, it doesn't appear as though there is a particularly happy camp at Milanello, and that's all without mentioning Mario Balotelli.
Hidden away behind all this paper talk is the upcoming Derby della Madonnina, which perhaps has more importance than usual this season given that both teams have fallen below expectations and psychologically it could be a significant boost for the winning team.
As mentioned above, the Europa League discussion will not go away despite the six-point gap with three games remaining, as essentially if the Rossoneri secure all three points on Sunday night, they move within striking distance of leapfrogging their city rivals in the standings.
Certain supporters will continue to look at Roma as the example to follow, given that the capital club have benefited significantly from no European distractions this season which has seen them challenge for the Scudetto throughout the campaign, and that is essentially what the rebuilding process needs next year.
Yet the message from within the club continues to preach the requirement of Milan competing on an international level, albeit in the Europa League, and regardless of outside opinion, the Rossoneri want to be involved in European football at some level next season.
However, the message on Sunday should be one that considers the supporters more so than the league table, as ultimately a derby with Inter is a special occasion that has created history through the years.
Riccardo Montolivo spoke about how this game represents an opportunity for Milan to redeem a season that has not been great, and that this is a "derby of pride" which is important in its own context.
It is difficult to disagree with the club captain in that sense, and while Galliani has labelled the Nerazzurri as the favourites on Sunday night, a win for Milan could be the lift that everyone at the club needs to fill the newspaper columns with positivity rather than cynicism.
For all the latest Milan and Serie A news, you can follow Sumeet on Twitter @italiafooty