AC Milan begins its post-crisis rebuild under new manager Rubén Amorim, but the Rossoneri's reconstruction faces an immediate complication: star winger Rafael Leão appears headed for the exit, with no concrete offers materializing from his preferred destinations in the Premier League or La Liga. The Portugal international, whose relationship with the club fractured after last season's fifth-place finish cost Milan a Champions League spot, is valued between €60M and €70M—a price tag that has so far deterred European suitors, leaving Middle Eastern and Turkish leagues as likeliest alternatives.
Why This Matters:
• Financial pressure: Missing Champions League could cost Milan €70M-€130M in lost revenue, roughly 25% of annual turnover.
• Squad overhaul: Two marquee signings—defender Mario Gila (€30M) and striker Gonçalo Ramos (€70M)—signal owner Gerry Cardinale's commitment to immediate competitiveness.
• Leão's uncertain future: Without firm bids from top-tier European clubs, Milan's most talented player faces a crossroads as his relationship with the club deteriorates.
Owner Cardinale Takes Direct Control
Gerry Cardinale, the RedBird Capital Partners founder who acquired Milan in 2022, arrived at the club's Milanello training complex by helicopter on July 13 to oversee the first day of pre-season preparations. His hands-on presence marks a shift toward direct oversight after last season's failure to secure Champions League qualification—a disaster that triggered the dismissal of the CEO, sporting director, technical director, and previous manager.
Cardinale's long-term strategy hinges on a proposed 70,000-seat stadium, modeled on American sports franchises, which would elevate Milan's matchday revenue to Premier League levels. However, that infrastructure windfall won't arrive until the 2031-32 season at the earliest. In the meantime, the club must reinvest carefully: commercial revenue has jumped from €82.1M to €143.4M over three seasons, but missing Europe's elite competition last year left a gaping hole in the budget.
The American investor has pledged to reinvest positive cash flow into the squad rather than extract dividends, and his visible presence at training—alongside lunch with players—underscores his promise to manage the club firsthand rather than from afar. Yet the Leão situation tests that commitment: selling the winger would recoup significant funds but signals pragmatism on sporting ambitions.
Leão's Departure Appears Likely
Rafael Leão's public criticism of Milan after last season has not been forgotten. The 27-year-old attempted to soften his stance once Amorim—his compatriot and former Sporting CP coach—was announced, but club officials appear unmoved. Leão's contract runs until June 2028, yet Milan appears to view him as a saleable asset rather than a cornerstone of the project.
Tottenham Hotspur has been the most frequently linked destination, with Milan reportedly offering the player directly to the London club. Leão himself is said to be "ready to say yes" to Spurs if a €60M bid arrives, but Tottenham's hesitation suggests they are not "particularly enthusiastic" about the deal. AS Roma has also been approached with a loan-plus-obligation formula, while FC Barcelona has conducted preliminary scouting without advancing to negotiations.
Outside Europe, the options are more concrete. Clubs in the Saudi Pro League have made initial approaches, and Galatasaray has tabled a contract proposal worth €10M per season plus bonuses—nearly double Leão's current Milan salary. Given the lukewarm European response, a non-European move has become increasingly plausible if his preferred targets in England or Spain fail to materialize.
The impasse reflects a broader reality: Leão's inconsistency last season—combined with his wage demands—has cooled interest from elite clubs who might otherwise gamble on his explosive pace and dribbling. For Milan, the situation is both financially and tactically uncomfortable. Amorim's 3-4-3 system could theoretically accommodate Leão as a wing-back or inverted forward, but the Portuguese manager has inherited a squad he did not select, and the club's leadership has indicated its preference for a pragmatic resolution.
New Signings Arrive with High Expectations
Milan has moved decisively to address defensive and attacking gaps. Mario Gila, a 24-year-old center-back, joined from Lazio on July 10 for €30M, with Real Madrid collecting half that sum due to a sell-on clause from his 2022 transfer. Gila has signed a five-year contract worth €4M-€5M net annually. Last season, he started 31 Serie A matches for Lazio, logging 2,481 minutes with a 6.98 average rating on FotMob. Though he recorded no goals or assists, his ball-playing ability and distribution fit Amorim's preference for possession-based defending.
Gonçalo Ramos, the €70M striker from Paris Saint-Germain, represents Milan's most expensive signing. The 25-year-old Portuguese international will wear the number 9 shirt and slot into the central striker role in Amorim's front three. Ramos scored 6 goals in 30 Ligue 1 appearances last season, often deployed as a substitute, but his form at the 2026 FIFA World Cup has been electric: he netted 4 goals in the knockout rounds, including the winner against Croatia in the round of 16, before Portugal's elimination in the quarterfinals.
Ramos made an unscheduled visit to Milanello on July 13, technically still on vacation, to meet Cardinale and Amorim and tour potential residences in Milan. "Hello Milanisti, I'm really happy to be here and can't wait to meet you. Forza Milan!" he posted on club social media after purchasing his own number 9 jersey at the Milan Store. The gesture, while informal, projects enthusiasm that Milan fans hope translates into goals.
What This Means for Milan's Immediate Future
Amorim addressed the squad with a tone of collaborative humility on his first day: "You should introduce me to the staff because you know them better than I do. I'm truly happy to be here, really proud. For anything you might need, I'm here. I'm available. For every discussion with other players, I'll defend you—if you're right." The message was clear: accountability, mutual respect, and a clean slate.
But the manager faces a truncated pre-season. Key internationals remain absent due to the World Cup or scheduled vacations, meaning Amorim has yet to work with his full squad. Milan will conduct a series of high-profile friendlies followed by a commercial tour through Australia and Asia before the 2026-27 Serie A season kicks off in mid-August.
The club's objectives are clear: secure an immediate return to the Champions League, play attractive, attacking football, and restore confidence among a fanbase disillusioned by years of near-misses. However, with the Leão situation still unresolved and a compressed timeline before competitive play resumes, outcomes remain uncertain. Amorim's reputation for tactical innovation and man-management—he won two Primeira Liga titles with Sporting and briefly managed Manchester United before being dismissed in January 2026—offers hope, but rapid results will be essential to validate the club's strategic overhaul.
Impact on Expats and Investors
For foreign residents in Italy and international investors watching Serie A, Milan's reset carries broader implications. The club's commercial growth and stadium ambitions position it as one of Italian football's most globally oriented franchises, but on-field instability threatens that brand. A successful Amorim tenure could accelerate Cardinale's plan to monetize Milan's intellectual property through digital engagement and international sponsorships, potentially increasing the club's valuation ahead of a future sale or public offering.
Conversely, another season outside the Champions League would deepen financial strain and raise questions about RedBird's ability to compete with state-backed rivals in England, France, and Saudi Arabia. The Leão situation exemplifies the dilemma: retain an underperforming player, or cash in and reinvest pragmatically? Cardinale has publicly stated he has final say on every transfer, a centralized approach that mirrors American sports ownership but runs counter to Italian football's tradition of empowered sporting directors.
For now, Milan's rebuild is a work in progress. Amorim's tactical system, Gila's defensive solidity, and Ramos's goal-scoring potential offer reasons for cautious optimism. But until Leão's future is resolved—and until the team proves it can compete in the evolving landscape—Milan remains a club in transition, balancing ambition with the harsh arithmetic of modern football finance.
