Official: AC Milan will 'play to win' with new CEO Calvelli
Quick summary
AC Milan's new CEO Giorgio Calvelli states the club will 'play to win' following his appointment, signaling an ambitious strategic direction.
Full article
Attributed to original sourceMilan formally announced that Massimo Calvelli is their new CEO, as Gerry Cardinale and RedBird restructure the entire management team. ‘We will play to win, instead of playing not to lose.’
MILAN, ITALY – SEPTEMBER 03: Gerry Cardinale of AC Milan looks on before the Serie A match between AC Milan and FC Internazionale at Stadio Giuseppe Meazza on September 03, 2022 in Milan, Italy. (Photo by Marco Luzzani/Getty Images) The Rossoneri made a clean sweep the day after failing to qualify for the Champions League, sacking coach Max Allegri, director of sport Igli Tare, CEO Giorgio Furlani and technical director Geoffrey Moncada.
They have decided after much deliberation not to appoint a new director of sport or technical director, streamlining the process to give RedBird chief Cardinale more control,
Today, Calvelli was formally announced as the new Chief Executive Officer of Milan, as RedBird pushed out the last remaining representatives from former owners Elliott Management.
There was a transfer strategy summit at Casa Milan, including Cardinale, Calvelli, Director of Player Trading Hendrik Almstadt, Director of Football Intelligence Bobby Gardiner, and chief scout Donato Lomonte.
Calvelli appointed new Milan CEO RIYADH, SAUDIA ARABIA – FEBRUARY 28: In this handout image provided by PIF, Massimo Calvelli, CEO, ATP (L) and Kevin Foster, Head of Corporate Affairs, PIF (R) The Public Investment Fund (PIF) unveil a new multi-year strategic partnership, marking a shared commitment to enhancing global tennis for players, fans, tournament organizers and stakeholders at all levels of the sport on February 28th, 2024 in Riyadh, Saudi Arabia. (Photo by PIF via Getty Images) “Since joining RedBird last year, Massimo has distinguished himself as a leader and driver of organizational design that brings people together and establishes a culture of collaboration and professionalism,” Cardinale said in the statement on the official club website.
“Massimo has co-led our investment in AC Milan along with RedBird partner David Castelblanco, both reporting to me. Our model at RedBird often requires our senior leadership to go ‘in house’ in our most important investments to ensure best in class execution, especially in situations requiring change and innovation. Massimo has demonstrated an ability to be effective in all these areas as he integrated himself into AC Milan over the last year.
“The mandate is clear – we will play to win, instead of playing not to lose – in everything that AC Milan touches, but most importantly on the field.
“The entire organization at AC Milan will now benefit tremendously from his full time appointment and sense of urgency to bring a winning culture and results back to the Club.”
That comment about ‘playing to win’ was seen as a jibe at former coach Allegri, who is still battling for a better severance payment so he can take over at Napoli.
Calvelli had worked in sport before, as CEO of the ATP tennis circuit from 2020 to 2025.
“The opportunity to lead AC Milan as it navigates this critical moment in its football trajectory as well as within the overall state of Italian football is something I take very seriously and with a profound sense of urgency,” Calvelli told the club website.
“The mandate from Gerry is to bring a culture of winning and results both on and off the field back to AC Milan – a culture worthy of the heritage that the Club represents within the European football community and our over 600 million fans worldwide.
“I’ve had a full year working collaboratively with the senior leadership of the Club across all functions and have a hands on sense of what needs to be fixed and innovated.
“I’m personally excited to work closely with our new Head Coach Ruben Amorim and his team which are already integrated and working well with our existing senior football leadership.”
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What happened
AC Milan has officially announced Giorgio Calvelli as its new CEO. In his first public statements, Calvelli emphasized a 'play to win' philosophy for the club, suggesting an aggressive and ambitious approach to both on-field performance and business operations. The appointment comes as Milan continues to navigate its post-Red Bird Capital era, with the new leadership expected to drive both sporting and commercial objectives. Calvelli's message signals intent to compete at the highest level domestically and in European competition.
Chance analysis
A new CEO appointment at a major club like AC Milan rarely has immediate on-field impact but sets the strategic tone. Calvelli's 'play to win' rhetoric suggests investment in the squad and sporting project, which could translate to more aggressive transfer activity and pressure on the coaching staff. For prediction systems, this is a long-term structural signal rather than a short-term performance factor.
AC Milan likely to pursue more aggressive sporting and commercial strategies under new CEO Calvelli, potentially leading to increased transfer investment.
Treat as background structural news; no immediate change to match predictions but watch for consequent transfer market activity from AC Milan.