AC Milan: Cardinale’s Director Search Heats Up as Tiago Pinto Emerges as Top Candidate

FolioPitch.com – 11 October 2026 | Gerry Cardinale‘s vision for AC Milan is taking shape, and the club’s hierarchy is on the verge of a significant addition. As GdS Cardinale continues director casting Tiago Pinto one of two leading candidates, the Rossoneri are meticulously evaluating their options to fill the newly created Head of Football role. The position is designed to oversee sporting operations, transfer negotiations, and day-to-day football matters, a strategic move by Cardinale to bolster the club’s management structure.

Cardinale, the RedBird Capital founder, has been proactive in reshaping Milan since his takeover. Last Saturday, he made a surprise visit to Milanello, the club’s training ground, not just to observe training but to hold a series of meetings with key figures. Among those present were CEO Massimo Calvelli, Director of Football Intelligence Bobby Gardiner, Director of Scouting Donato Lomonte, and Football Intelligence analyst Tiago Estevao. The discussions centered on finalizing the management setup, with the Head of Football role a top priority.

The search has narrowed down to a shortlist of candidates, with GdS Cardinale continues director casting Tiago Pinto one of two leading candidates highlighting the seriousness of the pursuit. Tiago Pinto, currently the head of football at Bournemouth, has emerged as a frontrunner. The Portuguese executive boasts over a decade of experience in Italian football, having served at Roma, where he gained deep knowledge of Serie A and the international market. His track record includes notable discoveries at both Roma and Benfica, and his crowning achievement was guiding Bournemouth to a historic sixth-place finish in the Premier League last season. Pinto’s familiarity with the Italian landscape and his proven ability to identify talent make him an attractive proposition for Milan.

However, Pinto faces stiff competition from Markus Krösche, the head of sporting affairs at Eintracht Frankfurt. Krösche has been a long-term target for Milan, with his name linked to the role since June. The German has a contract with Eintracht until 2028, but there is a possibility of an early exit. His departure seemed imminent in recent weeks, yet it hasn’t materialized, perhaps indicating that he is awaiting a formal agreement with Milan. Should Krösche make the move, his right-hand man, Timmo Hardung, could also join him at San Siro. The Eintracht duo represents a compelling package, but Milan’s interest in Pinto suggests they are keeping their options open.

Adding to the mix is Medhi Benatia, the former Udinese, Roma, and Juventus defender. Benatia transitioned into a director role at Marseille but was later dismissed. The Moroccan is intrigued by the prospect of a role at Milan, though it remains uncertain whether the feeling is mutual. His experience in Serie A and his leadership qualities could be assets, but Milan’s hierarchy appears to be prioritizing candidates with more extensive executive backgrounds.

Cardinale’s commitment to restructuring is evident. He has already revolutionized the squad, and he intends to further strengthen it in the upcoming transfer windows. The plan includes acquiring top-tier players on the level of Gonçalo Ramos, Diego Moreira, and Mario Gila. But before those moves can be executed, the management structure must be finalized. The Head of Football will work collaboratively with the existing team, ensuring that decisions are made collectively while bringing a fresh, international perspective to the table.

The coming days are crucial. Cardinale is expected to conduct further interviews, likely in London, as he narrows down the list. The process is thorough, reflecting his desire to appoint the right individual to drive Milan forward. As GdS Cardinale continues director casting Tiago Pinto one of two leading candidates, the football world watches with keen interest. The appointment will not only shape Milan’s transfer strategy but also signal their ambitions under RedBird’s ownership.

In conclusion, AC Milan’s search for a Head of Football is reaching its final stages. With Tiago Pinto and Markus Krösche as the leading candidates, the club is poised to make a decisive hire that could define its trajectory. Cardinale’s hands-on approach and willingness to invest in top talent underscore his determination to restore Milan to the pinnacle of European football. The next few weeks will reveal who will take on this pivotal role, and the impact could be transformative for the Rossoneri.