When Milan takes to the San Siro pitch for the final time this season, fans will be watching not just a match but the end of an era. While the team’s hopes for European soccer have already been dashed, Saturday’s fixture against relegated Monza could carry far more emotional weight than the league standings suggest. More than ten players may be playing their final game in red and black, and uncertainty looms over the futures of stars like Christian Pulisic, Rafael Leao, Joao Felix, and Santiago Gimenez.
The mood at San Siro has been one of resignation as a campaign that began with ambition winds down with disappointment. Back-to-back defeats at the Stadio Olimpico, including a 3-1 loss to Roma, have sealed Milan’s fate. Without European action for next season, the pressure is mounting to reset and rebuild.
According to Calciomercato’s Daniele Longo, 11 players have already mentally and physically prepared for life away from Milan. The list includes Joao Felix and Kyle Walker, who are both set to return to their parent clubs, Chelsea and Manchester City, respectively, following loan spells. Riccardo Sottil, on loan from Fiorentina, is also not expected to be signed permanently.
Veteran defender Alessandro Florenzi will see his contract expire on June 30, and no renewal appears to be in sight. Other likely departures include Ruben Loftus-Cheek, Samuel Chukwueze, and Filippo Terracciano, all of whom are reportedly close to sealing transfers away from Milan.
In addition, Fikayo Tomori, Malick Thiaw, Yunus Musah, and Emerson Royal have been named among those whose futures lie elsewhere. These moves signal a dramatic overhaul as the Red and Blacks prepare to reshape a squad that has underperformed across multiple fronts.
Star trio could also exit
The uncertainty doesn’t end there. Reports suggest three of Milan’s most important players—Mike Maignan, Theo Hernandez, and Tijjani Reijnders—could also be sold. All three are attracting interest from major European clubs, with Reijnders reportedly drawing attention from Manchester City.
“Tare will have to deal with the limbo state of Mike Maignan, Theo Hernandez, and Tijjani Reijnders as soon as he arrives at Casa Milan,” writes Longo. The club’s incoming sporting director, Igli Tare, will be tasked with decisive action from day one.
And what about the big names?
Amid the speculation, Christian Pulisic and Santiago Gimenez have notably not been named among the eleven expected to leave. However, Rafael Leao’s name has surfaced in German reports, with Bayern Munich allegedly in contact with his agent, Jorge Mendes.
Pulisic, despite a solid season, may find his position under review if the Rossoneri choose to cash in or overhaul their attacking structure. Santiago Gimenez, who arrived with promise, might still be given time to prove his worth—though a change in management could complicate that.
