AC Milan have appointed Massimo Calvelli as their new chief executive officer, consolidating a sweeping overhaul of the club’s management structure following their failure to qualify for the Champions League.
The announcement formalises RedBird founder Gerry Cardinale’s restructuring of the Serie A giants, which saw head coach Max Allegri, director of sport Igli Tare, chief executive Giorgio Furlani and technical director Geoffrey Moncada dismissed in a single day. The departures came immediately after the Rossoneri missed out on Champions League qualification, prompting a complete reset of the football leadership.
In a significant structural shift, the club have opted not to appoint replacements for the sporting director and technical director positions. This streamlines the decision-making hierarchy and grants Cardinale more direct control over football operations, completing the transition from former owners Elliott Management to RedBird’s preferred governance model.
Calvelli’s Mandate
Calvelli arrives in the role after co-leading RedBird’s investment in Milan alongside partner David Castelblanco, reporting directly to Cardinale. The 51-year-old previously served as chief executive of the ATP tennis circuit from 2020 until 2025, bringing experience from professional sports administration outside football.
Cardinale praised Calvelli’s impact during his first year with the investment firm, noting he had proven adept at uniting staff and fostering a collaborative, professional environment. He explained that RedBird’s approach often requires senior figures to work directly within portfolio companies during periods requiring “change and innovation.”
Calvelli outlined an aggressive new mandate for the seven-time European champions. The priority, he said, is to “play to win” rather than “playing not to lose” across all aspects of the club, particularly on the pitch. He described the opportunity to lead the club during this “critical moment” as carrying a “profound sense of urgency” to restore results befitting the club’s heritage.
The new chief executive will work closely with recently appointed head coach Ruben Amorim. A transfer strategy summit has already convened at Casa Milan involving Cardinale, Calvelli, director of player trading Hendrik Almstadt, director of football intelligence Bobby Gardiner and chief scout Donato Lomonte, indicating immediate priorities in the recruitment market.
Calvelli emphasised the need to restore a “culture of winning” that produces results across all areas of the operation, both on the pitch and commercially, for the club’s global fanbase, which exceeds 600 million supporters. He noted that his year spent working with senior leadership had given him practical insight into what requires improvement, signalling an active approach to addressing the squad’s recent shortcomings.