The myth of a guaranteed starting spot is gone.
On Wednesday, July 23 at 1:30 PM Italian time, Milan will kick off their competitive season with a friendly against Arsenal, and no fan has any certainties about the team that will play in Serie A and the Coppa Italia. Milan have four guaranteed starters: Mike Maignan, Luka Modric, Christian Pulisic, and Rafael Leao are untouchable. Everything else is up for debate. Who would you choose to play? Here's the position-by-position breakdown.
Transfer market: first pick
The starting right-back will be a new face, and there's still a lot to be written here. Unless there are surprises, Guela Doué will not arrive, and Marc Pubill is not a priority. There is no shortage of right-backs in the squad, whether natural or adapted. Alex Jimenez is a candidate for that spot, although under Massimiliano Allegri he could end up playing further forward, as an alternative to Christian Pulisic or Rafael Leao. Filippo Terracciano started as right-back in Saturday morning’s friendly against Milan Futuro. Alexis Saelemaekers started his career as a right-back and hasn’t forgotten how to play there, even though he’s evolved into a wide midfielder or right winger. There’s also Emerson Royal, who is out of the project: he could go to Besiktas or elsewhere, likely on loan.
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Four players for two spots
Fikayo Tomori and Pavlovic are the theoretical starters, the players Tare and Allegri are betting on most. Matteo Gabbia and Thiaw are the alternatives. But one question is logical: can Tomori and Strahinja Pavlovic actually play together under Allegri? Some qualities are clear, but so were the box errors last season. They didn’t play well together. Easy prediction: Matteo Gabbia and Malick Thiaw will get their chances and will fight for them, unless someone comes calling for Malick in the next 40 days. After turning down Como, a departure now seems unlikely.
Pervis Estupinan, the man who once sold empanadas, is the top candidate
AC Milan made an offer to Brighton and will make another soon. Tare has chosen him as Theo Hernandez’s heir and, if all goes as expected, Milan’s left-back will be Ecuadorian. His backup will be Davide Bartesaghi, a left-footer raised at Milan. But there are plenty of emergency options: Alex Jimenez, Strahinja Pavlovic, Alexis Saelemaekers. All of them have played as left-backs at least once in their careers. In the end, one big rule must be kept in mind: Milan will play one match per week. The issue won’t be the lack of alternatives, but rather avoiding chronic bench-related discontent.
Luka Modric is coming to play, and there's little doubt about him
He will get minutes, likely as the deep-lying playmaker in front of the defense. Ricci starts as his natural understudy—a learning period under the best. He will play often. There are two spots in midfield to fill, and a young man from Belgium is reaching for one: he wants it. If Ardon Jashari arrives, he will clearly be a starter. You don’t spend 35 million euros on backups. For the other spot, Loftus-Cheek and Fofana are the logical candidates… and here it’s hard to predict the future.
Ruben Loftus-Cheek is the player Allegri is most curious about: he has the physique and can score goals. But he needs trust and is coming off a poor season. Fofana is more consistent and more defensive: he’ll get his chances. To round it out: Musah and Bondo. Musah is the most likely to depart, while Bondo seems like the logical sixth man in rotation.
And finally, the number 9
The center-forward is the most important signing, but also the most complex, because center-forwards in this world are expensive—more and more so: goal inflation. There are many candidates. None truly favored. Boniface is well liked and doesn’t have an impossible price tag, but there are doubts about his injuries. Dusan Vlahovic is out of budget but has been in long-term conflict with Juve: impossible now, maybe in August who knows. Nuñez was the first option, but his cost is very high and there’s Arab competition. Arokodare fits the profile outlined by Tare and has a chance. Embolo is appreciated and could be signed tomorrow for 15 million euros. In addition to that, there’s also Santiago Gimenez, already in the squad, bought for 35 million euros six months ago.
There's a better chance of hitting the jackpot than correctly guessing all 11 starters in Milan's 2025-2026 starting lineup.
