The biggest question hanging over AC Milan right now is whether Rafael Leao will still be a Rossoneri player when the transfer window closes on September 1. Owner Gerry Cardinale met Leao at Milanello on August 21 to determine his future, with manager Ruben Amorim having made clear the Portuguese winger no longer fits his plans. Galatasaray and Saudi Arabian clubs have made offers, while the preferred Chelsea move has cooled considerably. The outcome of that meeting will define the shape of Amorim's squad for the season ahead.

The transfer activity surrounding Milan this week tells a broader story of rapid squad reconstruction. Diego Moreira, the Belgian winger who impressed at Strasbourg, was confirmed as the club's fourth summer signing, joining Gila, Gonçalo Ramos and Diawara. At nearly 70 million euros, the 19-year-old is seen as the wide player Amorim specifically requested and his arrival effectively closes the door on Leao's role in the team. Meanwhile, a move to send Santiago Giménez to Porto has stalled after Milan rejected the Portuguese club's loan proposal, leaving the Mexican striker's future unresolved with days remaining in the window.

On the pitch, Milan beat Manchester United 4-2 in their final pre-season friendly, providing a positive boost before the Serie A campaign begins. Their first league match takes them to Torino on August 23, with the pressure of a new era under Amorim making that opener feel significant. A high-profile clash with Juventus follows on September 6, giving the squad little time to settle before facing serious tests.