Milan and the Karetsas Regret: The Inside Story That Left Cardinale Frustrated
There’s a name that has been circulating in Rossoneri circles for weeks — a name that, according to sources close to the Milan world, could have reshaped the entire structure of the squad entrusted to Ruben Amorim: that name is Karetsas, a young Greek talent who ultimately signed for Borussia Dortmund. A missed opportunity that, based on behind-the-scenes reports, reportedly left Gerry Cardinale quite disappointed with how the club’s leadership handled the negotiations.
A Summer Window That Started Brilliantly
Credit where it’s due: Milan’s summer transfer activity got off to a flying start. As early as 6 July, the day of pre-season training camp at Milanello, the club had already confirmed two high-profile signings: Gonçalo Ramos for €75 million and Mario Gila for €30 million. Significant investments, executed with purpose and speed. Ramos even cut his holiday short to greet his new teammates, a sign of genuine commitment to the project. Gila was already on the pitch for the first session. A first-class start, by any measure.
But right at the moment when momentum was at its peak — when two or three more quality additions were needed to round out the squad — things started to stall. And the missed opportunity has a very specific name.
Karetsas: The Ideal Profile for Amorim’s System
According to what has emerged, Milan made a genuine and serious attempt to sign Karetsas in the attacking midfield role. The Portuguese coach had already given his blessing, convinced that the young Greek’s profile was a perfect match for his footballing philosophy: excellent technique, pace, left-footedness, and the ability to play on the right side of a three-man attacking midfield line — the exact position where Milan still needed a definitive answer.
The fee being discussed was under €40 million — a perfectly reasonable figure for a young talent of that calibre in today’s European market. Not a financial risk, but a calculated investment. And yet Borussia Dortmund moved faster, sealing the deal with the decisiveness that so often separates winners from runners-up in the modern transfer market.
Cardinale’s Frustration: The Board Under Scrutiny
This is where things became delicate. Gerry Cardinale — according to multiple sources — was visibly dissatisfied with the club’s failure to land Karetsas. The issue was not so much Dortmund’s success, but rather the pace at which Milan’s leadership had operated: the Rossoneri reportedly moved too slowly, allowing the German club to jump the queue. Cardinale had viewed that third signing as the crowning piece of what was otherwise a positive window, and watching it slip away was not easy to accept.
The episode highlights a broader truth: in modern football, the speed of execution often matters as much as financial firepower. Decision-making processes at the club level need to be sharper and faster.
Hutchinson and Moreira: The Solutions Found
To address the gap left by the failed pursuit of the Greek attacking midfielder, Milan moved in the final stages of the window: Omari Hutchinson arrived from Nottingham Forest, a versatile winger with Premier League experience, alongside Diego Moreira, capable of operating on either flank. Solid additions, no question — but born from a reactive rather than proactive approach, unlike the Karetsas pursuit, which had been planned well in advance.
The tactical question remains open: will Hutchinson be the regular starter in the No.10 role, or will Amorim lean on Rabiot in that position? His coexistence with Christian Pulisic — one of Milan’s most dangerous weapons — will need time and careful management. The French midfielder already knows the group’s dynamics well, while the English forward of Caribbean heritage is still an unknown quantity in the context of a club with the expectations and pressure that come with the AC Milan badge.
Looking Ahead to January: The Window Is Not Closed
The end of the summer transfer window does not close Milan’s transfer story. Both Cardinale and Amorim appear to share a clear vision: January will serve as a natural continuation of the work started this summer. The plan seems to be to observe the squad in competitive action, identify the specific areas that need reinforcement, and intervene with precision in the winter window.
Football, as ever, remains unpredictable: a player could emerge and make a certain type of signing redundant, while an injury or a dip in form could make another position a priority. The squad will be assessed match by match, and January will be used to complete what the summer couldn’t fully resolve.
Milan remain a club with the quality and ambition to compete at the highest level, and the awareness of where improvements are needed is itself a sign of a healthy, forward-thinking organisation. With Amorim at the helm and the drive of RedBird ownership, Rossoneri fans have every reason to look ahead with confidence and optimism.
