National break is over, Milan turns attention to the return to the league (Sunday, at San Siro, against Fiorentina) but the transfer market has never been put aside. Recent injuries to key players with their national teams have further exposed the squad’s limits and confirmed, if confirmation was needed, that the roster is too short even in a season without European competitions. Something will have to be done in the winter transfer window (January 2–February 2, 2026) in every department to strengthen the squad.
In the winter market, Milan will likely target an experienced central defender.
The club will also aim to sign a pair of wingers for Allegri’s 3-5-2 system, one per flank. The midfield is considered sufficient (with Ardon Jashari returning to training in November, this area has depth), so Milan will probably hunt for an additional attacker. The current forwards are Christian Pulisic, Santiago Giménez, Rafael Leão, and Christopher Nkunku. They may not be enough.
Giménez arrived at Milan for 35 million euros, including bonuses, from Feyenoord in the winter 2025 window, but so far he has not justified the investment. His commitment is unquestioned, but performance has been poor. Milan expected the Mexican striker to deliver 25–30 goals per season to elevate the team’s level, but results have been minimal. A January sale is not ruled out. Leão’s experiment as a central striker, interrupted by a 40-day calf injury, is still untested. Important updates are expected in January.
Sporting director Igli Tare is in talks with Pini Zahavi, Robert Lewandowski’s agent, who will leave Barcelona in the next summer market. For January, Tare supports Allegri’s idea and keeps active contacts with Darko Ristić, agent of Dušan Vlahović. The Serbian striker, born in 2000 and ending his Juventus contract this season, is Allegri’s preferred target.
The transfer fee would be low, under 15 million euros. His salary would be 5 million euros net for the rest of the season, and around 6 to 6.5 million euros next year. Vlahović could accept if Milan acts quickly. If he chooses to leave on a free transfer and stay at Juventus until June, Milan would be out of the international competition, Bayern Munich included.
Not everyone at the club supports investing in Dusan Vlahović. RedBird, the US ownership group, prefers not to violate its principles, as it did with Luka Modrić and Adrien Rabiot, and possibly with Lewandowski, and would aim for a different profile, as pointed out by Pianeta Milan.
A young striker, possibly more expensive in transfer fee (around 25 million euros) but with a much lower salary, who could be resold at a higher price to generate a major future profit. CEO Giorgio Furlani favors a signing like Nicolò Tresoldi from Bruges, who fits RedBird’s cost parameters and has been a lifelong Milan fan, idolizing Filippo Inzaghi.
