Calvelli: A Growing Presence in the Milan Universe
Massimo Calvelli, former CEO of the ATP in the world of tennis and operating partner at RedBird Capital, continues to expand his sphere of influence within the Rossoneri world. According to reports from Calcio e Finanza, Calvelli has joined the Board of Directors of Stadio San Siro Spa, the company entrusted with the ownership of the area on which the Giuseppe Meazza stadium stands and with the development of the new stadium.
He replaces Cirio, who is stepping down from the board — a transition that is far from coincidental. Calvelli had already joined the AC Milan Board of Directors in November 2025, although his entry into the RedBird ecosystem dates back to July of that same year. As highlighted in our recent in-depth piece, Calvelli is Cardinale’s new right-hand man, a presence that is becoming increasingly structured and far-reaching within the club.
The New Stadium: A Strategic Priority for RedBird
Joining the board of Stadio San Siro Spa is no minor detail. The new stadium project is one of the cornerstones of Jerry Cardinale‘s entrepreneurial vision for AC Milan: a modern, club-owned venue capable of generating independent revenue streams and consolidating the club’s position among Europe’s elite. Having a fully trusted figure inside that company says a great deal about the direction the American fund intends to take the project.
Calvelli moves comfortably between Casa Milan, matchdays at the stadium and international summits alongside Cardinale. His profile — managerial, international, rooted in elite sport — makes him an ideal tool for handling complex dossiers such as the stadium infrastructure project.
The Leadership Question: Decision Time Is Near
But there is a more pressing issue concerning AC Milan’s future — one that goes beyond Calvelli alone. With the season drawing to a close and Champions League qualification now within touching distance, the time for major changes at the top of the club is fast approaching. The question is not whether something will change, but how much will change.
Over the past four years since RedBird took over the club, sporting results have fallen short of the expectations befitting a club of Milan’s history and prestige. Last season’s eighth-place finish remains a difficult stain to ignore — a campaign that saw only the head coach and a few players depart, while the management structure remained largely untouched. Giorgio Furlani (CEO), Zlatan Ibrahimović (senior advisor), Geoffrey Moncada (head of scouting and development), Paolo Scaroni (president) and Igli Tare (sporting director) are figures who, in various capacities, embody the continuity that many supporters and insiders are calling an end to.
The concept is straightforward: a good football executive must be able to combine financial results with sporting results. Of course, a positive balance sheet matters — but simply selling key players like Strahinja Pavlović, Tijjani Reijnders, Sandro Tonali or Theo Hernández is not enough to define a virtuous management approach. The real challenge is building a competitive squad capable of winning the Scudetto while keeping the finances in order.
The Milan of the Future: Clarity and Structure
The model many are calling for is the traditional and streamlined one: a CEO, a sporting director, a head coach. Three figures working together with a clear chain of command — no overlapping roles, no interference, no conflicting voices. A model that has always worked in Italy and that clubs like Juventus, Inter and Napoli adopted with great success during their best years.
The Champions League is a starting point, not a finishing line. As repeatedly emphasised, a third or fourth-place finish is the bare minimum for a club of Milan’s stature — not an achievement to celebrate. The true rebuilding — the one supporters have been waiting for — must come through bold decisions at the top, regardless of the final league position.
The coming days and weeks will tell us a great deal. In the meantime, Calvelli watches, grows and positions himself. His real impact on the Rossoneri’s future is still entirely to be written.
