Milan is burning through managers while the boardroom plays games

The managerial search reflects a club without a compass

Milan is currently auditioning coaches as if they are selecting a mid-table squad rather than a European giant. The news that the leadership intends to meet Matthias Jaissle highlights a scattergun approach to recruitment. According to recent reports, Milan is set to discuss the vacancy with Jaissle, despite his current commitments at Al-Ahli. While his tactical pedigree is clear, placing such a high-stakes role on a coach currently tied up in the Saudi Pro League feels like a gamble born of desperation.

The club has also pivoted toward Oliver Glasner for a meeting scheduled for tomorrow. This pursuit confirms a lack of ideological consistency within the hierarchy. One day you are talking to a coach known for high-pressing intensity and the next you are vetting a manager with a different tactical profile entirely. Fabrizio Romano has noted that the board is trying to understand if Glasner can truly be the man for this transitional period, as Romano suggested in his latest update.

The boardroom distraction is the real rot

Managers come and go, but the structural uncertainty surrounding the ownership is alarming. It is impossible to build a coherent sporting project when the very people overseeing the operation are open to selling portions of the business to outside interests. The recent chatter involving a Fenerbahce presidential candidate eyeing a stake in the club should be setting off alarm bells for every supporter who values long-term stability.

Why is a club of this pedigree seemingly open to fragmented ownership structures? A strategic partner is one thing, but bringing in actors from outside the traditional European football hierarchy suggests the current financial models are not delivering the intended returns. This creates a vacuum in the boardroom that inevitably trickles down to the training ground. When players see their third prospective coach in as many summers, the tactical buy-in vanishes by the second month of the season.

Tactical drift is already baked into the next season

Whoever eventually takes the job faces a massive uphill climb. The lack of a clear philosophy means the recruitment team is operating in the dark. Without a specific system mandated by the top, the club risks buying players who do not fit the next manager's preferred shape. We saw this with last year’s signings, where the roster looked disjointed during stretches of the campaign. Even a manager as disciplined as Glasner would likely struggle to implement an effective 3-4-2-1 structure with a squad built for a different look.

Furthermore, the reliance on external consultants and high-profile journalists to confirm meetings creates an atmosphere of instability. It undermines the authority of the sporting director. If the public knows every candidate the club is checking into, the leverage in negotiations inevitably shifts toward the manager. Milan needs to stop the leaks and define their identity before they commit to a three-year contract with a coach who might not even suit the existing dressing room personnel.

The cost of stagnation

Consider the metrics: Milan has failed to maintain a consistent high-pressure intensity compared to top-tier rivals. To reach the Champions League elite, a club must average an xG differential of at least +0.7 per match. Milan hovered significantly lower for long periods last term. Whoever arrives must immediately fix the spacing between the lines, which was repeatedly exploited in big fixtures during the spring. The final points gap to the top of the table wasn't just a matter of luck; it was a symptom of a squad that lacked a defined defensive trigger.

We are nine days away from the start of a massive summer for the sport. Yet, while the rest of the world prepares for the World Cup cycle, Milan is still in the HR department. They are losing precious time in the transfer market, ensuring that whoever takes the job will be handed a pre-assembled squad that may not be capable of executing their tactical demands. Unless the ownership settles on a vision—not just a, candidate—the 2026-2027 season is likely to be a repeat of the current cycle of frustration.