AC Milan's season has taken a dramatic turn, with the Rossoneri watching their once-comfortable lead over rivals evaporate. While they still hold their fate in their own hands, the recent slump has sparked urgent discussions behind the scenes at the San Siro.

Owner Gerry Cardinale made a surprise visit to the squad following the disappointing Atalanta clash, attempting to rally the troops ahead of the final two matches of the campaign. However, the writing may already be on the wall for several key figures in the club's hierarchy. The front office has become increasingly fractured, and Cardinale now faces tough decisions about who stays and who goes among CEO Giorgio Furlani, sporting director Igli Tare, technical area head Geoffrey Moncada, and senior consultant Zlatan Ibrahimovic.

Perhaps the most intriguing storyline revolves around manager Massimiliano Allegri. Cardinale is reportedly keen on continuity and would prefer to keep the experienced tactician at the helm. But nothing is guaranteed. If Milan fail to secure Champions League qualification, or if Allegri's contract demands prove too steep, the club could be forced to part ways with one of football's most decorated coaches. Finding a replacement of similar caliber won't be easy, but the hierarchy may opt for a fresh direction entirely.

The uncertainty extends to the pitch as well. Star winger Rafael Leao has emerged as a potential departure, though interest has been surprisingly tepid—even from deep-pocketed Saudi Arabian clubs. According to reports, Milan would now settle for around €50 million for the Portuguese international, a far cry from the valuations they once placed on him. Leao recently passed up an opportunity to extend and improve his contract, adding further intrigue to his future.

For a club that prides itself on style and ambition, this season's trajectory feels all too familiar. Allegri's sides have historically struggled when their initial game plan gets figured out, with no reliable Plan B to fall back on. Yet given the questionable work of the front office in recent years—both this season and before—many argue that Leao should be the last player on the chopping block. After all, talent like his doesn't come around often, even in the fashion-forward world of Milan.