Gerry Cardinale returned to Milanello at 10:40 on Friday with Milan’s next institutional decisions high on the agenda. Having spent recent weeks abroad completing the Skydance transaction, the RedBird founder is again turning his attention to a club he reshaped heavily from last season but does not yet regard as a finished project.
A new football figure on Milan’s agenda
- Cardinale arrived at Milanello for a series of meetings with chief executive Calvelli, Football Intelligence director Gardiner, scouting chief Lomonte and Football Intelligence analyst Estevao.
- The discussions are expected to include the search for a head of football, a senior specialist intended to complement rather than replace the existing executive structure.
- Milan would retain collective decision-making, but Cardinale considers international football experience important as the club develops its sporting department.
- Further conversations with potential candidates are expected in the coming days, with London a possible venue for some of those meetings.
Cardinale took a prominent personal role in Milan’s summer recruitment, yet the club’s ownership now wants to add a dedicated football executive to give greater depth to its long-term planning. The work is therefore not limited to the next transfer window; it is also about defining who will lead the sporting side of the project in the years ahead.
Krösche remains the leading name
Markus Krösche, Eintracht Frankfurt’s sporting chief, has been the leading candidate since June. The German executive remains under contract with Eintracht until 2028, although there appears to be scope for an earlier departure.
His exit had looked close in recent weeks but has not yet been completed. Milan could be among the reasons for that delay, with Krösche potentially waiting for clarity over an agreement in Italy. Should he join, his Eintracht colleague Timmo Hardung could also make the move to Milan.
The Krösche-Hardung combination would bring an established working relationship, but Milan’s selection process extends beyond Frankfurt.
Other candidates in the frame
-
Tiago Pinto is well regarded after his work in Italy, Portugal and England. Now head of football at Bournemouth, Milan’s Europa League opponents, he knows Serie A from his spell at Roma and has experience of the international market through both Roma and Benfica.
-
Pinto’s recent record includes Bournemouth’s sixth-place Premier League finish last season, a historic result for the club.
-
Medhi Benatia is another possible option. The former Udinese, Roma and Juventus defender later worked as an executive at Marseille and is currently without a contract. A role at Milan would appeal to him.
The squad plan remains active
Alongside the management search, Cardinale’s plans are said to include further investment in the playing squad. Milan are expected to seek high-level additions in January and again in the summer of 2027, with Gonçalo Ramos, Moreira and Gila identified among the names being considered.
For Milan, then, this is not simply an office-room appointment. Cardinale’s visit reflects an effort to connect recruitment, analysis and senior sporting leadership as the club seeks to give its altered squad a more settled direction through the next stages of the Serie A season.
