The future of Christian Pulisic at Milan could soon be shaped by a decision unfolding far from the pitch. With speculation swirling across Europe and persistent whispers from Real Madrid, attention has turned to the fate of the Rossoneri’s head coach, Massimiliano Allegri.

As the season approaches a decisive stretch, the American star and the rest of the squad are watching closely while the club weighs its next move. Reports in Italy suggest that Milan has already reached an internal conclusion regarding the future of its coach, while Allegri himself has quietly made clear what direction he prefers. Yet the situation remains layered with intrigue, especially as Madrid once again circles around the veteran tactician.

The speculation intensified after reports from Corriere dello Sport suggested that Real Madrid is again considering Allegri as a potential manager for the 2026-27 season. The Italian newspaper reported that the Spanish giant “could make an attempt to hire Allegri next season,” reviving a connection that has existed for years. This would not be the first time Madrid has pursued the Italian coach.

The Spanish club previously approached Allegri in both 2019 and 2021, when the idea of bringing the experienced Serie A strategist to the Santiago Bernabéu came close to becoming reality. In 2021, the deal reportedly progressed to an advanced stage. However, the tactitian ultimately decided against the move after a crucial meeting with Juventus president Andrea Agnelli, opting instead to return to Turin after two years away from coaching.

Now, years later, the situation appears to be resurfacing again. Madrid’s leadership, led by club president Florentino Perez, continues to evaluate long-term options for the bench. The Spanish club’s recent managerial instability has only fueled the rumors. After replacing Xabi Alonso with Álvaro Arbeloa earlier this season, results have reportedly failed to meet expectations, opening the door for another change next summer.

Milan’s decision emerges

Despite the growing rumors from Spain, the situation inside Milan appears far clearer. According to multiple Italian outlets, including Corriere della Sera and La Gazzetta dello Sport, Milan is preparing to offer Allegri a contract extension that would keep him at the club until 2028, with an option for a further season.

The proposed deal would also increase his salary from $5.8 million to roughly $7 million per season, particularly if the club secures qualification for the UEFA Champions League. The decision reflects the Rossoneri’s belief that the experienced Italian boss should remain the central figure of the club’s long-term project. Club directors reportedly see continuity on the bench as vital for both recruitment and player development.

For a squad featuring key figures like Pulisic, managerial stability could prove decisive. Allegri’s return at San Siro has already restored structure and discipline to a team that struggled for consistency in previous seasons.

AC Milan head coach Massimiliano Allegri consoles Alexis Saelemaekers during the Serie A match.

Allegri’s own preference comes to light

Equally important is the stance of the coach himself. According to several reports, Allegri’s preference is to remain at Milan, a club he considers both professionally and personally significant. The Livorno-born manager has repeatedly emphasized his satisfaction with the current project.

While the 58-year-old manager appears committed to staying, he reportedly has specific conditions for the next phase of the project. The coach wants a stronger voice in Milan’s transfer strategy, particularly as the club prepares for a potential return to the Champions League. Playing in Europe would require a deeper squad capable of competing every three days.

Thus, discussions about the long-term plan are expected only after the season concludes, when Allegri and Milan’s leadership will evaluate the squad and define their strategy for the future.