Gerry Cardinale, owner of RedBird Capital, is set to take a more direct role in shaping AC Milan’s squad for the 2026-27 season, with Massimiliano Allegri central to those plans, according to reports in Italy. Cardinale will be present at San Siro for Milan’s match against Cagliari, hoping to secure Champions League qualification before initiating a significant overhaul of the club’s structure.
Should Milan qualify for the Champions League, Allegri will automatically receive a one-year contract extension, keeping him at the club until June 30, 2028. Cardinale intends to reassure Allegri of his long-term commitment to the project, citing the positive impact the coach has had since his return, guiding the team from eighth place last season to a potential Champions League spot. Despite a recent dip in form, Cardinale recognizes Allegri’s success in rebuilding the dressing room, securing Maignan’s contract renewal, and earning 42 points in the first half of the season.
Allegri is expected to request significant investment in the transfer market to manage the demands of competing on multiple fronts. A key target is Bayern Munich midfielder Leon Goretzka, who is available on a free transfer and has already held discussions with the Milan coach and management. Goretzka is reportedly waiting for confirmation of Champions League football before finalizing his move. Milan are also pursuing attacking options, with PSG’s Gonçalo Ramos identified as a priority, though the deal will be challenging to complete. Other potential targets include Borussia Dortmund’s Guirassy, Jackson, and Sorloth, while the situation of Juventus’ Vlahovic is being monitored.
The club is also considering the potential sale of Rafael Leão, with his cycle at Milan considered to be nearing its end following a season where he has not consistently performed as a central striker. Interest has been reported from Fenerbahce, with a presidential candidate requesting information on the Portuguese forward, as well as potential interest from Manchester United and Barcelona. A departure could depend on receiving a suitable offer and Leão’s performance at the upcoming World Cup. Further changes are expected within the club’s leadership, with speculation surrounding the future of current CEO Giorgio Furlani, though the club has denied reports of an immediate departure. Massimo Calvelli is expected to play a key role in identifying Furlani’s replacement, while the possibility of a role for Adriano Galliani, a club legend, is also being discussed.
