AC Milan have turned to a seasoned executive to steady the ship, but the scale of the task facing Massimo Calvelli is stark. On the same day the club confirmed his appointment as CEO, sources revealed they had rebuffed an approach from New York City FC for Christian Pulisic — a signal that the Rossoneri are not yet ready to spend big to arrest their decline. AC Milan name CEO amid Pulisic transfer approach
Calvelli arrives with a brief to “bring a winning culture” back to the San Siro, a phrase that will sound familiar to anyone who has watched Milan’s slide from Champions League contenders to Europa League hopefuls in a handful of seasons. The club’s hierarchy has gambled that a change in the executive suite can reset the trajectory before the next transfer window, but the window for patience is narrowing. The new CEO inherits a squad that still contains marquee names yet lacks the cohesion and cutting edge required to compete domestically, let alone in Europe.
## A CEO with a track record — but will it matter now?
Calvelli is no stranger to Italian football’s corridors of power. His CV includes spells at Inter Milan and Roma, where he was instrumental in shaping transfer strategies and commercial partnerships. At Inter, he worked under Steven Zhang during the club’s rise under Antonio Conte, a period that included Serie A titles and a Champions League final. That pedigree is why Milan’s owners opted for continuity with an outsider who understands the domestic market’s rhythms and the club’s global ambitions. AC Milan name CEO amid Pulisic transfer approach
Yet the timing raises eyebrows. Milan are six points adrift of leaders Juventus and 12 off pace in the title race, with a Europa League campaign that has already stalled. The club’s hierarchy insists the appointment is about long-term culture, not short-term fixes, but the absence of a marquee signing this summer — despite interest in Pulisic — suggests the board remains cautious. Calvelli’s first real test will be whether he can unlock the club’s commercial potential to fund the squad overhaul that supporters now demand. Milan’s commercial revenue has lagged behind Inter’s and Juventus’s for years; bridging that gap is central to any credible push for silverware.
## Pulisic rejection: a window on Milan’s transfer reality
The club’s decision to turn down an approach for Pulisic — a player who would have slotted into their attacking midfield and added Premier League pedigree — is telling. Sources close to the situation say Milan felt the offer did not meet their valuation, but the move also signals a broader reticence to spend freely. Pulisic, 25, has Champions League experience and a USMNT profile that could raise the club’s global stock, yet Milan opted to pass. AC Milan name CEO amid Pulisic transfer approach
That caution is understandable given Milan’s recent history. The club’s last two transfer windows have been defined by mixed returns: expensive buys like Olivier Giroud and Divock Origi have delivered experience but not impact, while younger recruits have struggled to break through. The Rossoneri’s wage structure is also a constraint; locking in a high-earning Pulisic would have required delicate salary negotiations. With the January window looming, Milan’s hierarchy may now look at cheaper options or loan moves, but the message is clear: the club is not yet ready to back big-money gambles under Calvelli’s watch.
## The squad’s fractures are showing
Milan’s current squad is a patchwork of talent and uncertainty. Rafael Leão remains one of Europe’s most exciting wingers, but injuries and inconsistency have blunted his impact. Olivier Giroud, now 37, provides experience but not the dynamism required to challenge for the title. The midfield, once a strength, has become a liability: Rade Krunić and Tijjani Reijnders have struggled to impose themselves, while Sandro Tonali’s ban and subsequent transfer to Newcastle have left a void. AC Milan name CEO amid Pulisic transfer approach
Defensively, the club has invested heavily in recent years — Simon Kjær, Matteo Gabbia and Alessandro Florenzi have all arrived for substantial fees — yet the backline remains shaky. The departure of key players like Theo Hernández and Rafael Tolói has exposed vulnerabilities that a new CEO and a restructured technical staff must address. Calvelli’s challenge is not just to sign players, but to rebuild a squad identity that has been eroded by years of managerial changes and tactical drift.
## What it means: a cultural reset or a bridge too far?
Calvelli’s appointment is a high-stakes gamble by Milan’s owners. The club’s recent history is littered with executive hires who promised transformation only to deliver incremental change. The arrival of Paolo Maldini and Frederico Chiesa as directors of football and sporting strategy, respectively, has not yet translated into on-pitch progress. Calvelli’s role is to align those appointments with a coherent commercial and sporting vision, but the club’s financial constraints mean any squad overhaul will be gradual.
The Pulisic snub underscores a deeper issue: Milan’s inability to attract top-tier talent on their own terms. The club’s global brand remains strong, but their appeal to elite players is waning. Pulisic, for all his talent, would have been a statement signing; his rejection suggests Milan are still seen as a destination of last resort for stars seeking a final payday or a move to Serie A. Calvelli must change that perception quickly if he is to convince the fanbase that the Rossoneri are serious about reclaiming their place among Europe’s elite.
Analysts point to Inter’s recent trajectory as a cautionary tale. The Nerazzurri’s rise under Conte and Zhang was built on smart recruitment, not just executive appointments. Inter’s commercial growth was matched by on-pitch investment, culminating in a Champions League final. Milan, by contrast, have relied on homegrown talent and a few shrewd buys, but the squad now lacks the depth and quality required to compete at the very top. Calvelli’s success will hinge on whether he can replicate Inter’s model — or at least arrest Milan’s slide before it becomes irreversible.
## What’s next: the January window and beyond
Calvelli’s first real test will come in January, when Milan must decide whether to back him with significant investment or continue their cautious approach. The club’s hierarchy has spoken of “bringing a winning culture” back to San Siro, but culture alone does not win titles. The January window is likely to see Milan target mid-tier free agents or loan deals, with a focus on shoring up the squad’s weakest areas. AC Milan name CEO amid Pulisic transfer approach
Beyond that, Calvelli’s long-term plan will depend on two factors: the club’s ability to monetise their global fanbase more effectively, and the performance of Maldini and Chiesa in identifying undervalued talent. The commercial department’s work will be critical; Milan’s kit sales and sponsorship deals have lagged behind their rivals, and Calvelli’s experience in the commercial side of the game could be the difference between incremental progress and a genuine resurgence.
For the fans, the appointment is a chance to believe again. But belief alone will not be enough. The Rossoneri’s next move must be decisive, both in the transfer market and on the pitch. Calvelli’s challenge is to prove that Milan’s owners are willing to back their new CEO with the resources required to turn the tide — before the club’s decline becomes terminal.
Sources
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