The summer 2026 transfer window at AC Milan is not just about signings. Before thinking about new additions, the Rossoneri hierarchy must first navigate a major squad clearout — a long and weighty list of players who are surplus to requirements, which, if managed well, could generate a war chest of over €100 million.
The Departure List: Long and Ambitious
The names on the table are numerous. Starting with the imminent sale of Pervis Estupiñán to Aston Villa, the list of departures includes high-profile names such as Fikayo Tomori, Youssouf Fofana, Ruben Loftus-Cheek, Ismael Bennacer, Filippo Terracciano, Warren Bondo, Álex Jiménez, and some fringe squad members including Musa and Samuel Chukwueze. The centrepiece of the entire operation — and potentially the most lucrative deal — remains Rafael Leão.
The Leão Situation: Offers That Haven’t Come
The future of the gifted Portuguese winger is the most complex issue to resolve. Leão, back from post-World Cup holidays, has shown over recent months a desire to embark on a new chapter away from Milan. The concrete, persisting problem is that meaningful offers from the Premier League, Bundesliga or La Liga have yet to materialise. There has been tentative interest from Turkey and Saudi Arabia, but the Portuguese star has made clear he is not keen on moving to those leagues. If top European bids don’t arrive, Milan could be forced to retain him — a scenario that would demand careful management to avoid any dressing room tension.
Tomori, Fofana and Loftus-Cheek: Urgent Solutions Needed
Three players representing three separate urgent decisions. Fikayo Tomori, the English centre-back who was once a cornerstone of the Rossoneri defence, is no longer part of the project. Youssouf Fofana, the French-Guinean midfielder, and Ruben Loftus-Cheek, the English box-to-box midfielder, complete a trio that Ruben Amorim does not consider central to his system. Keeping unhappy players is a double-edged sword: a footballer who knows he is not in the plans tends to train at reduced intensity, risks falling below peak condition and — crucially — can negatively affect the dressing room atmosphere.
The Strategy: Sell to Build
The principle is as simple as it is essential: you cannot keep buying without first selling. A squad of thirty or more players is unmanageable, both tactically and financially. The planned departures are therefore not merely a numerical exercise, but a necessary step to free up funds and squad space for the new signings already identified by the club’s leadership. The figure of over €100 million is deliberately conservative — when clubs know you need to sell, offers tend to come in low. But the sum remains considerable and, if realised, would give Milan a rock-solid foundation from which to build Amorim’s squad. The Estupiñán deal is an encouraging first step — now the pace needs to pick up.
