There was a big delay in proceedings because of the takeover by RedBird Capital Group from Elliott Management. That meant that the contract extensions of technical director Paolo Maldini and sporting director Frederic Massara took an age to negotiate and a lot of time early in the summer was lost.
They signed the deals at the last available moment but by then, they had lost control over moves for Sven Botman who joined Newcastle United, and Renato Sanches who eventually joined Paris Saint-Germain.
They have essentially been playing catchup since but on paper, the squad should still be better than last season. The real question is whether their improvements have been surpassed by the teams around them.
AC Milan signings
Charles De Ketelaere: This is the headline signing for Milan so far and is likely to remain as such. The youngster signed from Club Brugge for a reported €32 million plus bonuses after an extremely long negotiation with the Belgian champions. The Rossoneri have been following him for over a year and he could be a really special talent. He can play almost anywhere across the front line and will put a lot of pressure on the likes of Brahim Diaz, Junior Messias and Alexis Saelemaekers.
Divock Origi: This was a very swift piece of business from Milan which was conducted before the takeover and the subsequent confusion that brought. A lot of clubs wanted Origi when it became clear he would be leaving Liverpool and once he is fit, he will provide a great level of competition for Olivier Giroud whilst also opening up other tactical possibilities for Pioli.
Cathal Heffernan: Not one to trouble the first team this season but Heffernan became yet another example of an Irish youngster moving to Italy when he signed from Cork City after a successful loan spell with the academy.
As was to be expected, Alessandro Florenzi and Junior Messias both had their loan moves made permanent which help Pioli keep some continuity from last season.
It would be a big surprise if Milan ended the window with no one else. They are heavily linked with a host of midfielders in Ligue 1 such as Seko Fofana from RC Lens and Baptiste Santamaria at Stade Rennes. They also need a new centre-back for depth, with players like PSG’s Abdou Diallo, Tottenham Hotspur’s Japhet Tanganga and more being linked.
AC Milan summer sales
Franck Kessie: This is the only example Milan have of a key player leaving the club this summer. Luckily for them, it was known for a very long time that he would be going and it isn’t a shock. That being said, they are still searching for a midfielder after the lengthy and failed pursuit of Sanches. They’re not trying to directly replace Kessie but they need another body in that area, preferably with his versatility.
Alessio Romagnoli: It is something of a shame that Romagnoli’s Milan career fizzled out in the way it did but he left as a Serie A winner and he has joined Lazio, the team he supports, at a time when they really need him. This is another player that Milan are still trying to replace and will do by the end of the window.
Samu Castillejo: It became clear during last season that Castillejo had fallen to the bottom of the pecking order in attack at Milan so his departure seemed inevitable. He has joined Gennaro Gattuso’s Valencia side on a three-year deal. The fee is undisclosed but is thought to be minimal.
A host of other players have either had their loan moves away from the club made permanent, such as Jens Petter Hauge, or they have headed out on fresh loans, such as Mattia Caldara and Lorenzo Colombo.
Every AC Milan summer 2022 transfer
Ins: Charles De Ketelaere, Divock Origi, Alessandro Florenzi, Junior Messias, Cathal Heffernan.
Outs: Franck Kessie, Alessio Romagnoli, Samu Castillejo, Jens Petter Hauge, Leo Duarte, Daniel Maldini, Alessandro Plizzari, Marco Frigerio, Mattia Caldara, Lorenzo Colombo.