Krösche, Boto, Özek and Ausilio: A look at the four leading Head of Football candidates

It's no secret that AC Milan want to hire a Head of Football, but what is a bit more secretive is who they actually want. In the summer, it was clear that Milan wanted Krösche and when the German didn't arrive, they referred to internal hires as the solution.

However, by the end of the summer, suggestions were present that they still wanted Krösche. Read SempreMilan ad-free and get access to exclusive news.

Indeed, the idea of hiring a Head of Footballremained a priority for Gerry Cardinaleand this has only been proven in recent weeks. Several reports have stated the same idea - that the Rossoneri will make a hire before Christmas - and there are several names in the mix.

Tuttosport reportedfour names of interest for the club, so we thought it would be a perfect time to look through them, away from the October rush. Markus Krösche Krösche's name needs very little introduction.

The German was perhaps the most prominent figure of the summer and his arrival was a frustration for many, especially with him going on to renew with Frankfurt. Most saw him as a near-perfect candidate and we looked intowhy the combination of him and Ruben Amorimcould work well at the time.

In other words, this will be the shortest section of the lot. Nevertheless, he built a project to envy in Germany, with clear parameters.

A selling club, Frankfurt regularly turned a profit in the mercato whilst improving the squad. Responsible for finding several high-value departures for nominal fees, Krösche is a genius in all the workings of the mercato.

José Boto Boto is probably the most interesting name on the list. The 60-year-old Portuguese Technical Director has been with Flamengo since December 2024 and has overseen a few years of heavy spending and there has been a lot to show for that.

In just two and a half seasons, he's spent €137 million - usingstats from Transfermarkt- whilst only receiving €106m in inbound transfers. However, Flamengo broke their drought from winning the Brazilian Serie A title, winning the league twice in a row in 2025 and 2026, regaining the league for the first time since 2020.