The winter transfer window is approaching, and Milan plans to make 2-3 signings immediately to make the squad available to coach Massimiliano Allegri even more competitive in the fight for the highest seasonal targets. Executives Giorgio Furlani, Geoffrey Moncada, and Igli Tare are considering signing a new central defender, a new right winger who can play the entire flank, and, last but not least, a new forward.
Bought for 30.2 million euros plus bonuses from Feyenoord in the 2025 winter transfer window, Mexican forward Santiago Giménez has fallen short of Milan’s expectations across the board. He has been disappointing for the club, the coaching staff, and the fans. Furthermore, his physical and technical attributes do not seem to fit well with the 3-5-2 formation or Allegri’s style of play in general. Some Premier League clubs (Sunderland, Brentford, and West Ham) have tested interest in the “Bebote.” If he does not resist this time, unlike last summer, he will leave without regrets.
Who could replace Giménez at Milan in the 2026 winter transfer window?
Several names already linked to the club in the past are circulating, including Frenchman Jean-Philippe Mateta (Crystal Palace), Artem Dovbyk (Roma), and Niclas Füllkrug (West Ham). For the latter, Wolfsburg is also interested and wants to bring him back to the Bundesliga. One thing is certain: Allegri must approve any new central striker who replaces Giménez. He was already not thrilled about the signing of Christopher Nkunku in the summer, and now he has to change the “number 9” mid-season, as relayed via Pianeta Milan.
In recent weeks, Allegri’s preference for three names: Dušan Vlahović (Juventus), Mauro Icardi (Galatasaray), and Robert Lewandowski (Barcelona). Lewandowski could still join Milan, but only on a free transfer next season. For Vlahović and Icardi, the path to Milan, at least for the January window, is closed. Later developments may change that. Allegri could still have at his disposal another forward he has coached before, although not exactly as he had hoped.
Remember Kaio Jorge, the Brazilian forward born in 2002, who in summer 2021, while playing for Santos, seemed close to joining Milan but ultimately chose Juventus at the last moment? He had an unlucky two years under Allegri in Turin, suffering serious injuries. After a negative loan spell at Frosinone, Juventus decided in 2024 to sell him permanently to Cruzeiro.
Back in Brazil, Kaio Jorge has revived, and according to 'O Tempo' Allegri is considering trying again with the talented Brazilian forward, suggesting Milan sign him, similar to what he did with Adrien Rabiot last summer. The results are evident. Under contract in Brazil until 2028, Kaio Jorge is currently valued at 17 million euros. Aston Villa is also interested, but Allegri’s recommendation could carry significant weight for the player.
