Milan Seek a New Executive: Cardinale Wants to Strengthen the Sporting Structure
At AC Milan, the awareness is growing that the current management structure needs a significant addition. Gerry Cardinale, RedBird Capital’s owner and Milan’s principal shareholder, is said to have expressed dissatisfaction with certain aspects of how the summer transfer window was handled, which did not fully meet his expectations. This has generated a concrete need to bring into the club’s organogram an experienced figure from the football world, capable of supporting the technical staff and leading transfer operations with greater effectiveness.
The topic has been simmering for weeks, but in recent days it appears to have taken an increasingly defined direction. The stated objective is to have this new figure operational before the opening of the January transfer window, in order to plan ahead for the interventions needed to complete and strengthen the squad available to Ruben Amorim.
Summer Transfer Window Issues: What Didn’t Convince Cardinale
Behind this decision lie some concrete situations that are said to have left a bitter taste with the ownership. On the outgoings front, Milan failed to generate revenue from players deemed surplus to requirements: placing a player on the transfer list, while sometimes necessary, inevitably leads to a devaluation of their market value, making it almost impossible to receive adequate fees. A telling example: Fikayo Tomori, widely expected to leave, was ultimately reintegrated into the squad precisely because no suitable offers arrived.
On the signings front, Milan reportedly missed out on at least one priority target for the attacking midfield role — a profile identified as ideal to complete the forward line — who ended up at Borussia Dortmund due to a negotiation handled too slowly. Situations like these, reportedly, did not convince Cardinale of the effectiveness of the current sporting organisational model.
The Profile Sought: Traditional Sporting Director or Head of Football?
The role Milan are looking to fill could take different forms: a Sporting Director in the most traditional sense, or a Head of Football — a broader figure with overarching responsibilities across the entire football operation. In either case, it would need to be someone with direct experience at the highest level of European football, capable of engaging effectively with top agents, clubs and international institutions.
According to reports, Milan are looking predominantly abroad for this figure, meaning it is unlikely to be an Italian profile. This search should be distinguished from the one involving James Fontanella Cano, who represents a different kind of figure — with a more institutional role, likely involving the management of relations with Italian and international bodies and the media — whose precise position is still being defined.
Krösche in Pole Position, but the Situation Remains Open
Among the names that have circulated most insistently is that of Markus Krösche, current Sporting Director at Eintracht Frankfurt. The German executive has built a strong reputation in European football, demonstrating a remarkable ability to develop players and build competitive squads. However, his position at the German club is not yet settled: a recent internal meeting at Eintracht was held to clarify his future, but no clear signals of an imminent departure have yet emerged.
Krösche therefore remains a strong candidate, but he is not the only name on Milan’s list. The pool of candidates is said to be broader, with profiles from various European leagues under consideration. What seems clear — and this appears to be the real priority — is that Milan want to close this operation as soon as possible, perhaps using the international break to accelerate talks away from the pressure of the match calendar.
A Reinforcement with an Eye on the Future
As highlighted by Giorgio Furlani’s departure from Milan’s Board of Directors, the club is going through a phase of redefining its management structure. Bringing in a new head of the sporting area would be the logical completion of a restructuring process aimed at equipping Milan with the tools to match RedBird’s ambitions. An experienced executive working alongside Amorim could make the difference not just in January, but across the club’s entire medium-to-long-term planning.
