The week that could change everything: Milan must act now
Noticeably behind almost every other club in Serie A when it comes to both transfer market activity and technical appointments, AC Milan are now entering what could be the most important week of their summer. By 8 June, the club from Via Aldo Rossi is expected to make decisive moves on two critical fronts: the appointment of a new head coach and a sporting director — two roles that have been vacant for far too long and have been stalling any serious planning for the upcoming season.
The picture is well known: after weeks of uncertainty, with the club repeatedly changing its narrative on timelines, the time for words is over — action is now required.
Oliver Glasner: the profile that appeals to Cardinale
The hottest name in the frame for the Rossoneri dugout is Oliver Glasner, the 51-year-old Austrian manager who recently impressed at Crystal Palace in the Premier League, winning three trophies and demonstrating clear tactical nous and resilience in difficult moments. Glasner is a modern coach, known for his ability to work with mid-range squads and raise them to compete at the highest level — qualities that fit perfectly with Milan’s rebuilding project.
What makes his candidacy particularly significant is that Glasner is a target for Gerry Cardinale regardless of the Rangnick situation. Early reports suggested the Austrian coach might arrive as part of a package tied to Ralf Rangnick, but now the two negotiations appear to have separated: even without Rangnick, Glasner could still arrive at Milanello.
Rangnick: full control or no deal
The Rangnick chapter remains one of the most complex of this Milan summer. The German coach and football director — known for his revolutionary approach to the game and for launching the careers of managers like Klopp and Nagelsmann — has made clear he would be open to joining Milan as technical director, but only under one non-negotiable condition: complete freedom over technical and transfer decisions.
A demand that inevitably clashes with the existing power structure at the club, particularly with the hybrid role played by Zlatan Ibrahimović, who is simultaneously a club advisor, brand figurehead and a partner in the RedBird Capital Partners fund. The definitive answer from Gerry Cardinale is expected during this very week.
Further complicating matters is the Austrian Football Federation, which is doing everything possible to retain Rangnick by offering him a contract extension as national team manager. The Austria obstacle remains one of the main stumbling blocks on the path that could bring the German manager to Milan.
Glasner and Rangnick: independent paths
The key point to emphasise — and one that significantly changes the outlook — is that Glasner and Rangnick are not tied to each other. In recent weeks the assumption was a joint package: Rangnick as technical director, Glasner as head coach. Now, however, the dynamics appear to have evolved independently, opening up different scenarios:
- Scenario A: Rangnick agrees to Milan’s terms → Glasner could be his designated head coach.
- Scenario B: Rangnick renews with Austria or fails to reach an agreement → Glasner still arrives, with a different director profile brought in as sporting director.
The management structure: the real problem that needs solving
Beyond names, the most pressing structural question remains on the table: Milan need strong, cohesive leadership with clearly defined roles. Without this solid foundation, even the best available coach risks running into difficulties at the first sign of trouble. Recent history has made this painfully clear: both Paulo Fonseca and Massimiliano Allegri — an experienced manager, a Serie A winner with previous experience at Milan — paid the price for an unstable environment marked by internal conflicts and a lack of clear leadership.
Building a winning structure is the absolute priority: the right coach, the right sporting director and a chain of command respected by everyone. Only then can Milan return to competing at the highest level in Serie A and in Europe, honouring the tradition that figures like Braida, Maldini and so many others helped make immortal.
