In a summer that already promised change, Milan’s reappointment of Massimiliano Allegri has triggered a wave of uncertainty at San Siro. It’s his second stint with the Rossoneri, but this return comes under radically different circumstances: a failed campaign, managerial instability, and urgent financial strain. For a club once defined by strategy and control, the current chaos could cost Christian Pulisic three of his most influential teammates—an unsettling reality that leaves more questions than answers ahead of the new season.
Allegri becomes the fourth coach to take Milan’s bench in just a year, a staggering figure that reflects the tumult within the club. His return is not about continuity but crisis control. CEO Giorgio Furlani had no choice but to act after the Rossoneri’s collapse left them without UEFA Champions League soccer, costing the club roughly $113 million in lost revenue.
The financial gap includes UEFA prize money, commercial incentives, and sponsorship clauses that are now rendered void. As reported by Calciomercato, “it is reasonable to expect a revolution, but one that will have more economic constraints than in the recent past.”
Reijnders to Manchester City?
At the heart of this looming exodus is Tijjani Reijnders, a linchpin in midfield whose value has soared after a strong season. Though recently renewing his contract until 2030, Reijnders is heavily linked with Manchester City, who see him as a long-term project under Pep Guardiola.
According to Corriere dello Sport, “an offer from the English club is expected in the next few days,” with City aiming to open talks around $68 million, while Milan wants $80 million plus bonuses. The urgency stems from both parties wanting a conclusion before the Club World Cup later this month.
The player has reportedly agreed personal terms with the Premier League champions, leaving only the clubs to settle on a final figure. It’s a deal that appears all but inevitable. “The terrible season that AC Milan have had will leave a hole in the accounts, pushing Tijjani Reijnders towards Manchester City,” the report stated bluntly.
Premier League calls for Maignan too
Meanwhile, Mike Maignan’s future is equally uncertain. Though Allegri is reportedly keen to retain him, the French goalkeeper has yet to agree on a contract extension. His current deal runs out in just over 12 months, and Chelsea have begun formal talks, per multiple sources, including Sky Italia and Fabrizio Romano.
The Frenchman’s inconsistent form in the 2024-25 season has reportedly cooled Milan’s eagerness to extend his stay, with a previously agreed renewal now frozen. With Igli Tare installed as the new sporting director, the situation remains fluid—but without a signature soon, the club may have to cash in while they can.
Theo Hernandez and the Saudi temptation
Adding to Milan’s summer woes is the likely exit of Theo Hernandez, whose contract situation has deteriorated rapidly. A six-season veteran at the club, Theo is at a crossroads: accept a $4.5 million per year renewal (a pay cut) or move elsewhere.
So far, Milan’s offer has fallen far short of the $9 million per year that the star defender is demanding. Reports from Fabrizio Romano and Calciomercato confirm that Al-Hilal have agreed on a $40 million deal, pending the player’s final decision. The Saudi giants have offered an eye-watering $20 million net salary per season, and though no personal terms have been agreed, the club’s directors now expect Theo to depart.
“There is too much distance between what Milan is willing to offer and the demands of the left-back. Therefore, finding an agreement seems a truly impossible task,” wrote Corriere della Sera.
