A Roster Crisis Brewing at San Siro
AC Milan are facing a significant squad management challenge this summer as no fewer than nine players are set to return from loan spells across Europe, creating a roster logjam that will test the incoming sporting director from day one. The Rossoneri have players spread across Serie A, the Premier League, La Liga, and beyond — and each one represents a decision that will shape the clubs transfer strategy.
The situation has been dubbed la prova dei nove — the test of the nine — by Italian media, reflecting the scale of the challenge facing Milans new sporting leadership. With limited budget room and a squad already needing reinforcement in key areas, integrating or offloading nine returning loanees will require careful planning.
The Case of Ismael Bennacer
Perhaps the most concerning situation surrounds Ismael Bennacer. Even the unconditional support of Zvonimir Boban, who pushed hard to bring him to Milan in 2019, has not been enough to help the Algerian midfielder emerge from his prolonged crisis of form and fitness. Bennacer has struggled to recapture the dynamic performances that made him one of Serie As most promising midfield talents, and his return from loan adds another layer of complexity.
The club had high hopes that a change of scenery would revive his career, but reports from his loan spell suggest the same issues persist. Milans midfield already lacks depth in certain profiles, making the Bennacer decision particularly fraught — keep him and hope for a turnaround, or cut losses and reinvest.
Chukwueze Question Mark
Another significant question surrounds Samuel Chukwueze. The Nigerian winger spent the 2025-26 season on loan at Fulham in the Premier League, where he showed flashes of his considerable talent without consistently delivering. Fulham hold an option to make the move permanent, adding an element of uncertainty — if they decline, Chukwueze returns to Milan with a question mark hanging over his role.
The timing is awkward for the Rossoneri. With a new sporting director yet to be appointed, decisions on the returning loanees may need to be made before the new director has fully assessed the squad. The club hierarchy is aware of the ticking clock, as pre-season planning requires clarity on which players will be part of the squad.
Broader Squad Implications
The nine returning players represent a significant portion of Milans wage bill. Some, like Bennacer, arrived with high expectations that have not been met. Others were young prospects sent out for development and may now be ready to contribute. A few are experienced professionals whose best years may be behind them.
Milan sporting director candidate pool has been briefed on the situation, and the clubs ability to navigate this summer roster puzzle will be a key factor in attracting top candidates for the role. The next sporting director will need to make swift, clear-eyed assessments of each players future — with the understanding that getting these decisions wrong could set the club back in its quest to close the gap with Inter and Juventus at the top of Serie A.
