The first outing of Massimiliano Allegri’s new AC Milan leaves one big question: will it be a back three or a back four? The Livorno-born coach’s approach to this new chapter initially suggested a base 4-3-3 formation — more solid and balanced than the beloved old 4-2-3-1.
The latest friendly match against Arsenal in Singapore, however, was played with a clear setup featuring three natural central defenders and two wing-backs (Saelemaekers and Bartesaghi) ready to drop back into a five-man defensive line.
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Assuming we’re only talking numbers — when in reality, it’s the interpretation of roles and positioning that truly determines a team’s system — one thing is already clear: this Milan side needs a right-back, regardless of the starting formation. And by right-back, we mean someone who can play either as part of a back three or as a full-back. Even just entertaining the idea of relying solely on the decent options of Jimenez and Saelemaekers borders on blind optimism, as relayed via Milan Press.
The profile is clear: a player capable of filling that role with defensive awareness and, when required, able to support the attacking phase. Someone who combines athleticism with defensive solidity, without shying away from venturing into the opponent’s final third. Not someone like Estupiñán, to be clear — he’s a much more offensively-minded player.
The desired attributes narrow the shortlist down to two standout names: Guela Doué and Wilfried Singo. Both currently play in Ligue 1, both are valued above Milan’s usual €20 million range, and both can operate as part of a back three, a four-man defense, or even as wide midfielders in a 3-5-2 setup.
Doué is the club’s top choice
French club Strasbourg, however, are unwilling to sell and have set a high price: at least €30 million, including bonuses. Singo, meanwhile, has been offered to Milan, but Monaco won’t go below €25 million. For him, it would be a return to Italy after his spell at Torino — an experience in Serie A that shouldn’t be overlooked.
The common denominator?
A significant investment is needed, only then can Milan be competitive and finally secure a high-level right-back.
Why Milan needs to move fast:
With the Serie A season just weeks away, Milan’s management can’t afford to hesitate. Defensive consistency was a major issue last season, and the lack of a specialist right-back cost the team in both domestic and European competitions. Signing a player like Doué or Singo wouldn’t just address a tactical need — it would send a message: this is a Milan side ready to challenge at the top again.
Moreover, both players bring something rare: adaptability. In a league where managers frequently adjust formations mid-match, having a defender comfortable in multiple systems is a major asset. This versatility becomes even more valuable in European play, where opponents vary widely in style and tempo.
The financial balancing act:
Of course, Milan’s interest is also tied to financial strategy. After a summer of targeted reinforcements and a renewed focus on youth and resale value, committing over €25–30 million on a single defensive piece will require careful planning. However, with Theo Hernández on the left and Tomori anchoring the center, adding a dynamic force on the right would complete a balanced, modern defensive line.
One possibility being explored internally is a structured deal with bonuses based on appearances or Champions League qualification — especially in Doué’s case. This would allow Milan to stay within budget while still competing with Premier League clubs circling the same targets.
Exploring alternatives and internal solutions:
While the market continues to evolve, Milan’s scouting department is also evaluating less expensive — and perhaps more tactical — alternatives. The idea is not only to secure a short-term fix, but to identify a player who aligns with the club’s evolving football identity.
Emerging names from South America and Eastern Europe have appeared on internal shortlists, with some reports linking the Rossoneri to rising profiles from Brazil’s Série A and Croatia’s top tier. These regions continue to offer technically gifted players with strong resale potential — a key component of Milan’s business model under RedBird Capital.
At the same time, internal solutions are not entirely ruled out. Some within the coaching staff are quietly optimistic about Fikayo Tomori's ability to play on the side, if necessary, thanks to his pace and also Alex Jimenez, a young prospect who impressed last season. In fact, their tactical discipline and work ethic provide credible rotation options in the short term.
Allegri's tactical evolution:
One of the fascinating elements of this new Milan era is Allegri’s own evolution. Known traditionally for his conservative 4-3-1-2 or 4-3-3 formations, Allegri appears more open than ever to experimenting with hybrid systems — perhaps influenced by the growing tactical complexity in European football. In the last match against Arsenal in Singapore, for example, Allegri deployed a 3-5-2 formation.
The success of this shape, however, hinges heavily on balance — which circles back to the right-back (or wing-back) issue. A player who can defend, tuck in, and support in transitions is not a luxury. It’s a necessity in this system.
What fans should expect next:
With several weeks left in the transfer window, fans should brace for an intense finale. Milan is expected to offload several fringe players — including Ballo-Touré, Origi, and possibly Messias — to create both financial and squad space. The funds recouped will likely be reinvested immediately, and a defensive signing remains top priority.
Off the pitch, excitement around the squad continues to grow. As the team embarks on its international friendlies and early domestic fixtures, the hunger for silverware is palpable — both among the players and the fans.
And with such a young, talented core in place, the Rossoneri faithful have reason to believe that this season could mark a new high point in the club's recent history.
