The situation at San Siro is one of the most chaotic at any major European club this summer. Following the dismissal of Massimiliano Allegri, the club has conducted months of discussions with candidates including Glasner, Rangnick and Mauricio Pochettino — without arriving at a definitive answer on any of them.
According to La Gazzetta dello Sport, Glasner attended a six-hour face-to-face meeting with owner Gerry Cardinale and club adviser Zlatan Ibrahimović earlier this week. He arrived having studied the squad in detail, presented his vision for how the team would play, and left confident of receiving another call before the end of the week. Gianluca Di Marzio described Glasner as "the coach closest to the job" if asked today.
Rangnick's position is more conditional. The Austria national team manager attended a separate meeting with Cardinale and stated his terms clearly: he would arrive as technical director with full powers, bringing his own trusted personnel into the sporting structure, including Johannes Spors as sporting director and Christopher Vivell as head scout. For Rangnick, this is not a coaching role — it is an institutional restructuring.
That demand has met resistance. Di Marzio noted that Rangnick's requirements "clash with Ibra's desires," with Ibrahimović — technically an adviser to RedBird Capital rather than a Milan employee — determined to retain influence over sporting matters.
The tension between Rangnick's demand for a clean operating structure and Ibrahimović's continued involvement is described in multiple Italian reports as the central blockage.
La Gazzetta reported that Rangnick has set a deadline of the start of next week. Austria face Jordan in their World Cup opener on June 17 and the federations want clarity before the tournament begins. If Milan do not commit, Rangnick has signalled he will renew his Austria contract instead.
If Rangnick departs, the path clears for Glasner as head coach. But without the structural reset Rangnick would have demanded, the organisational problems that contributed to Allegri's dismissal — lack of a proper sporting director, unclear chains of authority — would remain unresolved.
The backup pairing of Ramón Planes as sporting director and Pochettino as head coach remains on the table, though the latter's involvement with the United States national team at the World Cup complicates the timeline.
For a club of AC Milan's history and ambition, this level of institutional drift into June is not a good look. The summer has started. The clock is moving. A decision cannot wait much longer.