Massimiliano Allegri’s return to Milan was supposed to bring stability. Instead, after a turbulent summer transfer window, the coach finds himself at the center of a tactical dilemma that could define the club’s season. With new arrivals reshaping the squad and injuries altering plans, Allegri has been forced to rethink his system entirely — and one of Milan’s biggest names, Christian Pulisic, may not be thrilled about it.
As Tuttosport reported, the Rossoneri’s sporting director, Igli Tare, hinted before the Lecce clash that the club will start the campaign with a three-man defence. That revelation has put into motion a cascade of questions: should Allegri continue with the 3-5-2 he has tested throughout preseason, or switch toward a more attacking 3-4-2-1? Either way, compromises are coming. The biggest unknown isn’t the defense — it’s the attack. Santiago Gimenez remains Milan’s only natural striker, but his role will depend on how Allegri aligns his supporting cast.
For Rafael Leao, a new challenge beckons. Once considered untouchable on the left wing, Allegri is now preparing to use him centrally. He has already experimented with Leao as a lone forward, as well as in a partnership. In fact, La Gazzetta dello Sport wrote: “For Leao, Max has the number 9 role in mind. An atypical one, but still at the heart of the attack.”
Alongside him, Christopher Nkunku arrives as the Rossoneri’s most expensive signing of the summer, a $43 million investment that gives Allegri a versatile weapon. Nkunku can operate as a false nine, a second striker, or even deeper as an attacking midfielder. Allegri admitted after the Lecce game: “I don’t know where I’ll use him. It depends on the match and the opponent.”
If the forward line is unsettled, the midfield is equally complicated. Adrien Rabiot appears untouchable, with Allegri having pushed hard for his signing. Luka Modric, brought in for his experience, may require the protection of a three-man midfield. Samuele Ricci and Youssouf Fofana offer dynamism, while Alexis Saelemaekers could prove vital on the flanks. The depth means the manager must choose between balance and creativity. In a 3-5-2, there’s room for more midfield protection, but in a 3-4-2-1, sacrifices will need to be made.
The Pulisic question
This is where the mystery deepens — and where Christian Pulisic enters the debate. The American was one of Milan’s most consistent performers last season, thriving in the 4-3-3 system that Allegri has now abandoned.
In the 3-5-2, Pulisic could be the one to lose his guaranteed starting spot. Allegri may ask him to reinvent himself — either as a second striker, an attacking midfielder, or even shifted wide in a more defensive role. None of those positions reflects where he has been most effective.
As Tuttosport explained, Allegri’s tactical calls could “sacrifice Pulisic on the flank, allowing Nkunku and Leao to form a high-speed pairing up front.” That reality may not sit well with the USMNT star, who expected to be a central figure again this year.
As Allegri experiments, Pulisic may be the player forced to adjust the most — or risk being left out of key games. What’s clear is that the experienced Italian boss has staked the club’s identity on a system that moves away from last season’s 4-3-3. The tactical shift explains why Milan abandoned their pursuit of a traditional No.9 and instead bet on Nkunku.
The gamble could pay off spectacularly, with Leao transformed into a modern center-forward and the Frenchman given freedom to roam. But it could also create friction, especially if one of Milan’s established stars — like Christian Pulisic — begins to feel sidelined.
