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Milan at a Standstill: Executive Turmoil and a Race Against Time?

Wajih by Wajih
5 June 2026
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Casa Milan view كازا ميلان

AC Milan's headquarters (Photo by Marco Luzzani/Getty Images)

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Within a constant whirl of names, scenarios, appointments and situations that are not aligned with the roadmap laid out ten days ago by Gerry Cardinale, the figure of Massimo Calvelli is emerging more and more each day as an extremely hands-on presence in Milan's internal dynamics. A trusted associate of Cardinale, Calvelli has been assigned some of the key responsibilities that had previously been in the hands of Giorgio Furlani, while others have been delegated to Paolo Scaroni.

Massimo Calvelli in an interim role at Casa Milan:

In practice, what Calvelli is currently experiencing is a period of regency as interim Chief Executive Officer. It was an almost inevitable solution, as corporate continuity was needed following Furlani's dismissal, despite the fact that Calvelli himself had reportedly made it known that he did not wish to take on the CEO role. Indeed, initial discussions had already begun with profiles such as Edwards from Liverpool and Ayre from Nashville, while Italian candidates were neither considered nor explored in depth, in what appeared to be a clear strategic choice by the shareholder. It is worth remembering that Calvelli is CEO International of RedBird Development Group and an Operating Partner at RedBird Capital Partners, and he also sits on Milan's board of directors. The latter point is far from insignificant.

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Speaking of Milan again, which is meanwhile still in the rebuilding phase, it remains to be seen what the next step will be...

The future of AC Milan's CEO role:

At the moment, however, it is too early to say whether Calvelli will ultimately become Milan's full-time CEO. But if there are no significant developments in the assessment of the various candidates under consideration, then the role could indeed fall to him. What is certain is that, in this situation, Calvelli would still want an operational sporting structure beneath him, allowing him to focus on the other responsibilities that typically fall under the remit of a chief executive officer.

Friday, 5 June. The usual refrain that Milan supporters know by heart: there is no head coach, no Sporting Director, no Technical Director, and no Chief Executive Officer. Meanwhile, other clubs are active in the transfer market (see Inter with Palestra) or are organising the upcoming season through strategic planning meetings (Allegri with Napoli). Milan, by contrast, is at zero. In fact, below zero. To be at zero there would at least need to be a foundation, and at present there is not even that. Beyond the absurdity of the situation itself, when has anyone ever seen Milan without senior executives and sporting leadership figures for more than ten days?, the timing is deeply concerning. Cardinale and Ibrahimović have not only failed to find the right people for the vacant positions, but many of the profiles they are pursuing will soon be occupied by the upcoming World Cup in the United States.

Rangnick-Milan: the national team coach left for the USA:

Much has been said about Ralf Rangnick. The German manager has, quite intelligently, refrained from making any "binding" statements. At a press conference he said that he neither confirms nor denies anything. A shrewd stance, given that he is currently Austria's national team manager, is highly regarded by the federation, and has a contract extension offer on the table. That issue therefore needs to be resolved first. But even if it is, Rangnick and his national team will soon depart for the United States. When? On 4 June, Austria travelled to the USA, where they will face a group that is anything but challenging, as relayed via Milan Press.

Austria's opening match at the 2026 World Cup is against Jordan, with kick-off scheduled for 6:00 a.m. (Italian time) on Wednesday, 17 June. The second match will be the most anticipated of the group: Austria will face Argentina on Monday, 22 June at 8:00 p.m. Italian time. The final group-stage match will be against Algeria during the night between 27 and 28 June, with kick-off at 5:00 a.m. (Italian time) on Sunday, 28 June.

Pochettino-Ibrahimovic in USA:

If Austria were to be eliminated in the group stage, which is hardly the most likely scenario, it would mean that Rangnick, assuming he accepted Milan's offer, would be free and available at the start of July, only a few days before the beginning of pre-season training at Milanello. The German manager will not be the only one occupied by the World Cup. Mauricio Pochettino, another name linked with the Rossoneri, will also be involved in the tournament. The United States, whose national team Pochettino manages, will play Paraguay, Australia and Turkey. Here too, imagining a group-stage elimination would be somewhat naïve. And do you know who else will soon be heading to the United States? Zlatan Ibrahimović. The RedBird Senior Advisor at Milan will be one of Fox Sports' leading pundits throughout the tournament, beginning on 11 June.

It is difficult to imagine finding oneself in such a situation, yet that is exactly the case. Regardless of what Cardinale's strategy for Milan ultimately proves to be, the timing has been, is, and will remain absurd. A season that risks beginning under a dying star rather than merely an unlucky one.

Zlatan Ibrahimovic AC Milan ميلان إبراهيموفيتش
Zlatan Ibrahimovic (AC Milan via Getty Images)
Tags: Milan
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Wajih

Wajih

A writer, passionate about football: Serie A and AC Milan in particular. For business inquiries, contact: wajihmzoughi1996 [at] gmail [dot] com

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