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Cardinale steps up, now experience can complete AC Milan’s project

Wajih by Wajih
10 September 2026
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Gerry Cardinale of AC Milan

The Rossoneri club owner Gerry Cardinale ahead of Serie A match Torino-Milan (Getty Images)

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The transfer window is over, and it would be far too simplistic to judge it solely by adding up the arrivals and departures. This summer has revealed something more important about Milan: a club can have ideas, financial resources and an ownership that is finally more involved, but without certain expertise within its structure, it can still risk losing control of situations.

The U-turn over Tomori, who was initially being ushered towards the exit before being brought back into the project, and the deal for French midfielder Youssouf Fofana, which collapsed when it appeared to be heading towards completion, are different situations, but they leave the same impression: at certain moments, AC Milan were chasing events rather than controlling them. And in the Italian transfer market, which is also shaped by relationships, timing, deals within deals and unwritten dynamics, the risk is that a technical problem turns into an embarrassing situation.

By the way, while the boardroom drama unfolds, supporters can still stay close to the action on the pitch, including every Serie A clash involving Milan, by following the matches and placing a quick bet on the Rossoneri’s next match, taking advantage the positive momentum created by head coach Ruben Amorim’s team who have won their first two league games of the season..

Between Gerry Cardinale and Ruben Amorim, experience is needed

Gerry Cardinale's presence during this transfer window was an important new development and deserves recognition. Ruben Amorim, on the other hand, inevitably had an influence on the construction of the squad by identifying the characteristics and priorities he wanted. But the ownership and the coach cannot be at opposite ends of a line without someone in the middle.

What is needed is a senior figure with genuine sporting experience, someone who knows the market, agents and clubs, and, above all, knows how to anticipate situations rather than having to chase them. Someone with the authority to tell Amorim no when a request is not worthwhile and, at the same time, explain to Gerry Cardinale why sometimes investing a little more means avoiding much more costly problems further down the line. There is no need to reinvent the role; it simply needs to be entrusted to someone who already knows the job.

There is a market between Mario Gila and Sankhoun Diawara

There is another limitation that this summer has exposed. It is understandable not to want to spend €30 million on every player and to also focus on young players who can increase in value. But between a major investment and a gamble, there is a whole world of players costing €10 million or €15 million who may have less long-term potential but are already ready to perform at the level AC Milan require.

A top club cannot afford too great a gap between its starters and their alternatives, because sporting objectives are also financial objectives: losing competitiveness means putting qualification, prize money, revenue and squad value at risk. At that point, the initial saving risks becoming nothing more than a cost pushed further down the road.

Milan owner Gerry Cardinale is making effort

Whatever one may think of his decisions, their timing and the way they were made, compared with what we had seen in the past, it cannot be said that Gerry Cardinale has not made an effort. Again, his decisions may or may not be shared, but the fact remains that after four years, the American owner has started doing what he had been loudly asked to do from day one: take an interest in Milan. He took advantage of the complete change in the coaching and management structure to centralise decision-making power in his own hands, personally stepping in to choose the coach and the players to sign. He has been seen with unprecedented regularity at Milanello, at Casa Milan and now alongside the team on matchdays as well. This does not mean that the last four years are erased, nor that he is doing everything right (once again, the results will determine that) but there can be no denying that his attitude has changed. And that can only be seen as a positive.

Why AC Milan's next signing should be a director:

Amorim could represent the beginning of a new cycle, while Cardinale's greater presence is a positive sign, but the transfer window that has just ended should have taught Milan a lesson: commitment and good intentions cannot replace experience. A fan can give a project time and even accept a few mistakes, but it is much harder to accept U-turns and deals falling through that give the impression of improvisation.

January is only four months away. Before even asking which player Milan will need, it would be wise to establish who will be responsible for identifying that player, negotiating the deal and explaining why he is the right choice. Because Gerry Cardinale can provide the money and Ruben Amorim can say what he needs. But between the two, there needs to be someone who knows how to do the transfer business.

Ruben Amorim and AC Milan owner Gerry Cardinale
Head coach Ruben Amorim and the Rossoneri club owner Gerry Cardinale (AC Milan via Getty Images)
Tags: Gerry CardinaleMilan
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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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