Last season, Milan was the team that earned the most points from losing situations last season (21, compared to Atalanta’s 19), a figure interpretable in two ways depending on your optimism. The first is that the team is often not fully present and concedes easily. The second is that in terms of quality, it is probably not inferior to anyone in Italy.
Now, the 2025/26 campaign should be the one of restoration for Milan in every sense. It is necessary to rebuild both at management and squad level after last season’s disaster. It is also a return to a classical approach, with a clearer distribution of powers: one of Italy’s most experienced sporting directors, who follows more traditional market paths, and the most conservative available coach. One poor season was enough to disprove last year’s technical project and reveal how fragile its foundations were.
The change of direction was necessary because last season’s problems reflected a command chain that did not work at all. There was no coherence between the squad and the chosen coaches, the locker room lacked reference figures, and perhaps the working culture at Milanello was not ideal.
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Creating a more professional environment:
This is crucial for the next Milan season. Moves like the sale of Theo Hernández and the arrival of Luka Modrić, whose presence alone should set an example, go in this direction. The same applies to Allegri’s appointment; he must not only coach but also fill some of the gaps that marked last season’s failure, similar to what happened in Juventus’ post-Agnelli transition.
Few doubt Allegri can handle such delicate matters. On the field, what can he give the Rossoneri? Milan’s squad still has a strong offensive orientation, and some players, especially in defense, do not fully match his ideas.
Allegri’s last months at Juventus, two years ago, gave the image of a coach too rigid. He established himself as one of Europe’s best for versatility, but in his second Juventus term, he seemed to have only one way to play, regardless of the opponent: the most reactive possible. Has anything changed in the year away from the field? Being in an environment that seems less obsessed with the false game-results debate could help him avoid sticking rigidly to his positions. Hard to say now.
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Allegri’s teams evolve over the season. He will likely use the first part to experiment and reach a final shape by the new year.
Until we see Milan at the season’s peak, we can draw some indications from the preseason. August football is not decisive, Fonseca’s Milan impressed in friendlies, but the first matches may give general guidance.
Leao must improve tactically under Allegri:
The first, perhaps most interesting, concerns Leão’s position. Tare is still seeking a center-forward; if no number nine arrives, Leão seems the main candidate because Giménez does not offer enough guarantees. Insiders report Milan very close to Victor Boniface, which would further complicate forward hierarchies.
In a transition-focused Milan, as Allegri may design against top teams, Leão could thrive as a striker, where his weak defensive tendencies are less harmful. With possession, as a striker, he would touch the ball less but could exploit vertical runs, a movement he used consistently only under Fonseca’s last months.
Leão in depth allows sudden verticality, as Saelemaekers shows; attacking the last line at the right moment, he will often reach the defender first and withstand contact. Regardless of starting position, it is important that Leão’s game does not stagnate, as it often has in recent years. Even starting from the left, he should not be confined to the wing, but vary his receptions.
Leão has not made a real leap only because Milan often gave him the ball to resolve impossible situations. He is self-sufficient, but always receiving static and without support prevented him from exploring his talent and improving.
Creating small synergies to amplify his potential will be important. Allegri says he wants to leave talent free, without too many instructions. At Juventus, long-distance attacks and mediocre teammates in decision-making rendered that freedom ineffective.
At Milan, this could change. Many top Rossoneri players move close to teammates to compress space and exchange. Estupiñan from the back, Jashari and Ricci in midfield, Pulisic and Saelemaekers ahead. And Modrić, expected to play twenty games that could change Milan’s attacking sense. They are dynamic players, enjoying position and ball exchanges. They do not need rigid structures. If they involve Leão in their approach, Allegri may be right: these are the players to leave free.
This Milan would not constantly control the ball and could sometimes be slow, but a few key moments would be enough to activate them and win matches.
Defense, Allegri's main concern, will handle the rest:
The team’s approach this year is easy to imagine. Formation details will become clear later. Against Liverpool, a 4-4-2 morphing into 5-3-2 was seen. Against Leeds, a 5-4-1, slightly higher.
Against Liverpool near midfield, Milan’s 4-4-2 had Saelemaekers wide and Tomori as full-back.
Milan will not defend too aggressively except in specific moments. Positional defense phases will vary depending on opponent quality. Do the Rossoneri have enough defensive quality?
The central defenders package seems weak for Allegri, even after signing the 19-year-old talent David Odogu from Wolfsburg. Pavlović is impulsive, not reliable in the box. Gabbia is reflective, but is he at Milan’s starting level? Tomori has been inconsistent in recent seasons; will a more demanding coach help him recover?
Midfield is also not solid off the ball. With possession, it suits Allegri for technical and physical qualities (Loftus-Cheek ideal, but endurance is an issue) and for midfielders’ touch and vision (Modrić, Ricci, Jashari). Without the ball, Milan lacks a true screen (Fofana is more aggressive and recovery-oriented, not a positional defensive midfielder).
Adapting the squad to Allegri's defensive idea may be difficult. Playing one match a week should help.
Best possible scenario?
Milan already started slow, losing against Cremonese (1-2), and then won in Lecce. Initial complaints arise, then a masterpiece against Bologna consolidates Allegri’s idea: Bologna dominates possession (70%) and makes 47 crosses, yielding 0.86 xG and 0 goals. Milan wins with Leão’s only strike. Fans regain some sense of joy for some time. January-February, Milan could even compete for the title. Allegri repeats something along those lines: “We must still be there in March, then we will see.” Derby win with a potential Modric goal restores confidence. Champions League qualification and optimism return.
Worst scenario?
Milan starts even slower, gains one point in three matche. A home defeat to Napoli raises doubts. Allegri calls for patience; Milan falters. Napoli, Inter, Juve lead; Roma, Como, Atalanta, Bologna outperform Milan. January, 0-1 loss to Fiorentina; fans boo while praising ex coach Pioli who would be gaining positive results at Fiorentina by then. Tare buys a Kosovar striker from Switzerland; too little. Ibrahimović posts vacation stories while team lacks direction. Season ends sixth with Coppa Italia semifinal. RedBird criticizes Tare and Allegri's project, returns full powers to Ibrahimović.
Who is AC Milan's key player for the 2025/2026 season?
Rafael Leao remains Milan’s pivotal figure. This season could be tactical year zero. Leão must step up and exploit freedom given by Allegri. Mentally, this is a year of maturity. During long defensive phases, he must stay engaged. At 26, anonymous seasons are no longer acceptable.
Which shirt should you get?
If you're also living in Milan as well as supporting the Rossoneri club, then you can see one of the greatest midfielders live: Luka Modric. This could be his only season in Italy. Therefore, take that shirt, especially if older fans had Boban's shirt, the player Modric considers his 'footballing father'. Modric chose number 14, from his early Croatia and Tottenham years: maximum romance.
