AC Milan have torn into the market with the confidence of a contender, reshaping the spine of the squad and recalibrating the wage bill. A new manager, a clear identity in pre-season, and rapid-fire moves have created momentum. What follows is a complete breakdown of the business, how it fits together, and what still needs doing before the window shuts.
Strategy Under Allegri And Why It Matters
Massimiliano Allegri’s arrival has sharpened the brief. He wants a compact block, immediate verticality, and control zones in midfield. That is why the club targeted profile fits rather than headline glamour. The spine has been reengineered to give structure and tactical flexibility, with a deliberate blend of prime-age legs and elite experience.
The Incomings And How They Fit
Samuele Ricci from Torino, €23m
Samuele Ricci addresses Milan’s biggest recurring issue, which was tempo control without sacrificing bite. Ricci offers press resistance, a reliable first touch under pressure, and metronomic short-range distribution. He can sit as a single pivot or play as a double pivot in tougher away matches. In Allegri’s build patterns, Ricci is the first out ball and the trigger for switches to the left channel.
Pervis Estupiñán from Brighton, €17m
Pervis Estupiñán brings acceleration and overlapping threat from left back. His crossing on the run is a useful weapon, and his recovery pace allows higher full-back starting positions. The question is whether Estupiñán can replicate the two-way dominance that Theo Hernández delivered at his peak. He will need early chemistry with the left-sided winger and the near-side midfielder to avoid isolation against deep blocks.
Luka Modrić, free transfer
Luka Modrić is the low-risk, high-value bet. Even in shorter bursts, Modrić still offers elite scanning, third-man runs, and tempo shifts that break compact shapes. His influence on Samuele Ricci and Ardon Jashari in training could be as valuable as his minutes. In tough Serie A games, Modrić remains the smartest problem-solver on the pitch.
Ardon Jashari from Club Brugge, €36m
Ardon Jashari looks like the engine signing. He is a high-volume ball winner who carries the ball into traffic and drives lines forward. With Ricci sitting, Jashari can step up to disrupt, then surge through contact to release wingers into space. His arrival raises the floor athletically and allows Allegri to toggle between a 4-3-3 and a 4-2-3-1 without losing compactness.
Koni De Winter from Genoa, €20m
Koni De Winter is the succession plan at centre-back. Comfortable defending large spaces, quick enough to cover behind an aggressive full-back, and composed on the ball, De Winter is a stylistic match for what Allegri wants on the right side of the pair. He is the direct answer to the outgoing profile and should push for minutes immediately.
The Outgoings And What They Mean
Tijjani Reijnders to Manchester City, €55m
Tijjani Reijnders departs as one of Serie A’s best progressive midfielders. The fee looks below the current market for his output, but the move unlocked the funds to complete multiple additions. Milan lose ball-carrying and late-arriving goals from midfield. The onus now falls on Ardon Jashari to absorb defensive volume and on Luka Modrić to replace creative touches in the half spaces.
Theo Hernández to Al Hilal, undisclosed
Theo Hernández had a dip last season but remained a unique outlet. Losing his left-side dynamism is significant. Pervis Estupiñán must prove he can replicate the sustained thrust, especially in matches where Milan pin opponents deep. Set-piece impact will also need redistributing across the group.
Malick Thiaw to Newcastle United, €35m
Malick Thiaw leaves a vacancy that Koni De Winter is clearly intended to fill. Thiaw’s aerial dominance and recovery speed will be missed in transitions. De Winter’s learning curve will be decisive in the first quarter of the season when fixture density spikes.
Francesco Camarda to Lecce, loan
Francesco Camarda’s loan is a development play. Consistent senior minutes should accelerate his penalty-box craft and sharpen his timing against compact back lines. Milan will monitor closely with a mid-season recall option a possibility if depth is tested.
Midfield Rebuild: From Reijnders To A New Core
Samuele Ricci and Ardon Jashari are the new foundation. Ricci sets rhythm and angles, Jashari injects force. Luka Modrić stitches phases and supplies the final touch of clarity in zone 14. On paper, this is a balanced trio that can alter height depending on game state. The trade-off is the loss of Tijjani Reijnders’ progressive power in stride. Milan will need third-man runs from wide players and late box entries from Jashari to offset that.
Defensive Reset: De Winter’s Test And The Estupiñán Question
Koni De Winter steps into a demanding role. He must command aerials, defend big spaces when the line pushes up, and pass assertively into midfield. Early partnerships with the goalkeeper and the right-back are crucial. On the left, Pervis Estupiñán offers an outlet but must show durability and concentration to avoid back-post lapses. Without Theo Hernández’s all-action game, Milan will look for set patterns that free Estupiñán on the overlap without exposing the channel.
Where The Attack Stands Right Now
Up front, the club wants a reference point who can finish at volume and occupy center-backs. Dusan Vlahovic is a natural ideological match. He provides near-post runs, back-to-goal security, and penalty-box gravity that opens space for runners. Rasmus Højlund has also been discussed as a development-plus-immediacy play. His straight-line speed, pressing energy, and willingness to attack space would fit Allegri’s transition plans. Santi Gimenez remains the current nine and will not want to cede minutes, which makes the pecking order a sensitive point for dressing-room balance.
Financial Picture And Risk Management
Fees in and out suggest a deliberate rebalance. Selling Tijjani Reijnders, Malick Thiaw, and potentially capitalizing on high-value assets has financed multiple positions with manageable wages. The risk is concentration. If Pervis Estupiñán underwhelms relative to Theo Hernández, or if Koni De Winter needs longer to adapt, Milan could feel immediate defensive regression. The hedge is depth and the ability to pivot in January if needed.
What Still Needs Doing Before Deadline Day
1. Add a striker who guarantees 15 to 20 league goals. Dusan Vlahovic is the cleanest stylistic fit if pricing and structure align.
2. Secure a wide attacker who can beat a man and carry goals from the flank if budget allows.
3. Finalize one outbound to maintain wage flexibility if incoming targets accelerate late.
Winners, Questions, And The Manager’s Hand
Winners include Samuele Ricci and Ardon Jashari, who walk into a system that highlights their strengths. Luka Modrić should thrive in targeted minutes and high-leverage situations. The big question is the left flank. Pervis Estupiñán must close the gap to Theo Hernández quickly. On the back line, Koni De Winter’s bedding-in period will define how brave the team can be without the ball. Allegri’s game plans will likely feature controlled aggression, early verticals, and compact rest defense to reduce exposure.
Projected XI And Rotational Notes
A likely shape uses Ricci at the base, Jashari to his right for ball winning and carrying, and Luka Modrić in the advanced role when control is needed. Pervis Estupiñán starts at left back with Koni De Winter on the right side of the central pair. In attack, Santi Gimenez leads the line unless a new signing arrives, with the possibility of a two-striker look late in games to chase goals. Rotation will be essential in a season with domestic and European commitments, and Modrić’s minutes will be managed to keep his interventions sharp.
## Verdict: A Smarter Squad With One Big Decision Left
On balance, this is a coherent window. Samuele Ricci and Ardon Jashari modernize midfield. Luka Modrić adds brainpower and calm. Koni De Winter refreshes a key defensive slot. Pervis Estupiñán is the swing piece who must hit the ground running. The attack still needs a definitive focal point. If Dusan Vlahovic can be landed on sustainable terms, the squad ceiling rises immediately. If not, Rasmus Højlund represents a compelling path with upside, provided the financial structure keeps flexibility.
## Final Word
Milan exit this phase of the window with clearer identity, better depth, and a platform for Allegri to impose structure from day one. One more accurate stroke in the number nine role would complete the picture. The foundation is in place. The next signing decides how high the roof can go.
