AC Milan Unveils New CEO Calvelli with a Mandate to Win

FolioPitch.com – 27 June 2026 | In a bold restructuring move, Official AC Milan will play to win with new CEO Calvelli, as the club announced the appointment of Massimo Calvelli to lead the Rossoneri into a new era. The announcement came after a tumultuous week that saw the dismissal of several key figures following failure to qualify for the Champions League. Gerry Cardinale, founder of RedBird Capital, made it clear that the club’s philosophy is shifting from a defensive mindset to an aggressive pursuit of victory.

Calvelli, who previously served as CEO of the ATP tennis circuit, has been integrated into AC Milan over the past year. His formal appointment marks the end of Elliott Management’s influence, with RedBird now holding full control over the club’s direction. Cardinale stated, “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.” This directive underscores that Official AC Milan will play to win with new CEO Calvelli, signaling a cultural shift at every level.

The restructuring includes the departure of coach Max Allegri, director of sport Igli Tare, CEO Giorgio Furlani, and technical director Geoffrey Moncada. Instead of replacing them with a traditional sporting director, RedBird has streamlined the hierarchy to give Cardinale more direct oversight. The new leadership team includes Director of Player Trading Hendrik Almstadt, Director of Football Intelligence Bobby Gardiner, and chief scout Donato Lomonte. Additionally, new head coach Ruben Amorim has already begun working with the existing senior football leadership.

Calvelli’s background in sports management, particularly his tenure at the ATP, brings a global perspective to the role. He emphasized the urgency of restoring a winning culture: “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.”

The “play to win” comment has been widely interpreted as a direct criticism of former coach Allegri’s pragmatic style, which often prioritized defensive stability over attacking ambition. Allegri is currently negotiating a severance package that could allow him to take over at Napoli. Meanwhile, the new leadership is focused on integrating data-driven strategies and innovation, aligning with RedBird’s investment philosophy.

Calvelli’s vision extends beyond the pitch. He plans to modernize the club’s commercial operations and fan engagement, leveraging his experience in global sports marketing. The club boasts over 600 million fans worldwide, and the new CEO is expected to strengthen AC Milan’s brand internationally. “We will play to win, instead of playing not to lose,” remains the guiding principle.

As the Serie A season progresses, all eyes will be on the impact of this restructuring. With a clear mandate from Cardinale and a streamlined management structure, Official AC Milan will play to win with new CEO Calvelli, aiming to restore the club’s status among European elites. The coming months will test whether this bold approach translates into tangible results on the field.

In conclusion, the appointment of Massimo Calvelli represents a fundamental shift in AC Milan’s organizational culture. By embracing a winning mentality and restructuring the leadership, RedBird is betting that innovation and aggression will bring back the glory days. Whether it succeeds remains to be seen, but the message is clear: the club is no longer content with merely participating; it is determined to dominate.