AC Milan’s season is still demanding depth across three competitions, yet the prospects of Fikayo Tomori and Ruben Loftus-Cheek have moved in different directions beneath the same cloud. One has returned from the margins without playing a minute; the other began the campaign as a regular option but is gradually losing ground as Ruben Amorim’s attacking midfield choices settle into place.
Neither player is expected to receive a new deal. Their present contracts run until June 2027, after which Milan intend to let both leave as free agents, removing close to €10 million in combined gross annual wages from the accounts. There may still be opportunities before then, particularly if suspensions or injuries alter the coach’s plans, but neither appears central to the club’s medium-term thinking.
Tomori back in the group, but still waiting
Tomori’s position has been especially delicate. During the summer he had been included among the players effectively placed outside the sporting project, to the point that he had not even been allocated a shirt number. When no agreement was reached over a departure from Milanello, Amorim chose to bring the English defender back into the first-team group.
That decision offered him a route back into daily work, rather than a clear restoration of status. The psychological challenge is evident for a player asked to resume training and compete after being told, only weeks earlier, that those excluded would not be brought back in. It also leaves a difficult relationship to manage with a coach who subsequently revised that stance.
Tomori remains an experienced defender, including at European level, even if he has not rediscovered the level he reached in Milan’s Scudetto-winning season. His profile does not entirely match the characteristics Amorim seeks in his preferred central defenders. That was underlined when Gila was rested against Benfica: Amorim selected Terracciano rather than Tomori.
The former Chelsea player is consequently still on zero appearances for the season. A few matches may arrive as the calendar develops, but they would not alter the wider direction. If a suitable solution emerges in January, Milan could consider an early exit and save half a season of his salary.
Loftus-Cheek’s shrinking role behind the forwards
Loftus-Cheek also looked likely to leave in the summer. Confusion around Milan’s attacking-midfield department, however, made it difficult to define who would depart and who would arrive, and Amorim ultimately kept him. The Englishman started almost every pre-season friendly and was initially used as one of the coach’s principal options behind the forwards.
Amorim has spoken positively about his qualities, describing him as complete, strong in the air and able to combine with the side, while adding that he must become more involved during matches. It is familiar territory for Loftus-Cheek, a natural central midfielder who has repeatedly been moved further forward during his time at Milan.
Continuity has been the missing element. Apart from a short spell, he has struggled to sustain form either from match to match or across 90 minutes. His imposing build has not always translated into the physical sharpness required, while operating in tighter advanced areas has exposed the need for quicker movement and faster decisions.
He has made five appearances so far, three from the start. Yet as the attacking midfield unit takes on a clearer shape, his place has weakened: he has started only once in Milan’s last four matches. Unlike Tomori, there are no current indications of a January departure. His expected farewell is instead likely to come next summer, leaving two English players to complete very different final stretches of their Milan careers.
