Milan and Amorim: The Old Trafford Lesson Returns to San Siro After Three Winless Games

I sat in row eleven of the press box at San Siro. That night Milan lost 2-0 at home to Benfica, and the first half unfolded like a tape stuck on slow motion. The ball circled the back three, switched flanks, came back, switched again. Not a single pass broke Benfica's midfield line. In the thirtieth minute, the first whistles rose from the Curva Sud. In the thirty-fifth, I wrote a line in my notebook: "They are not short of effort. They are short of a destination."

That was the moment I understood Milan's problem under Ruben Amorim is not attitude. It is structure.

A sentence I heard in a 2026 press box taught me to look at the person before looking at the match. Watching Amorim glued to the touchline for the entire first half, I saw a man trying to stay calm in front of the very system he built.

Context: two months and three matches

Amorim arrived at Milan in June, replacing Massimiliano Allegri. After a season away, Milan returned to European competition. Commercially that is a positive signal: broadcast money, matchday revenue and brand value from a Europa League place all exceed a domestic-only season. But sporting-wise it means a denser calendar, and a squad still finding its rhythm faces double the pressure.

Milan's last three matches: a draw with Juventus, a draw with Lazio, a 2-0 defeat to Benfica. Three games without a win. Two consecutive matches trailing by two goals. And in both of those matches, Milan conceded first.

That is raw data. Raw data says little unless placed next to how the team plays.

After the Benfica loss, Amorim said Milan create more problems for themselves in possession than when the opponent has the ball, and that turnovers happen in positions dangerous to their own goal. He also said the team lacks creativity near the box and does not create enough, despite coaching routines designed to generate more box possession.

These are important words because they land exactly on the wound.

Core: the problem is in possession, not in defence

Milan opened the season with a back-three structure, primarily 3-4-2-1, shifting at times to 3-5-2 to control midfield. This shape has been a debating point across Europe for two years. In England, Amorim was criticised for a perceived refusal to move away from 3-4-2-1. In Italy, Allegri had previously run a similar hybrid and drew similar complaints.

But here is the point I want to make plainly: Milan's problem is not the back three; it is that the player profiles do not match what the shape requires.

3-4-2-1 demands three specific things. First, two wing-backs who run the flanks relentlessly and create in the opponent's half, not merely hold position. Second, two No.10s operating in the inside channels, able to receive between the lines, turn and play the final pass. Third, a striker who can hold the ball up while team-mates arrive. Remove one link and the system still runs, but it does not arrive.

That is precisely what happened in the first half against Benfica. Milan had the ball, but the ball only travelled between three centre-backs and two central midfielders. When it reached a wing-back, nobody was in the inside channel to receive the return pass. When it reached the two No.10s, they were forced to face their own goal and recycle.

Anatoliy Trubin stood firm against every Milan attempt. But calling it a great goalkeeping display misreads the night. Trubin only had to deal with shots from outside the box, efforts taken under pressure. There was no save that truly stretched him.

On advanced metrics, I have no xG or PPDA to cite, and it would be dishonest to invent them. What I have is what my eyes recorded and what the coach himself admitted: Milan lose the ball in dangerous positions, and that is a rest-defence problem — how a team organises the moment it loses possession.

This is the nuance most commentary skips. When a side trails by two goals in consecutive matches, the reflex is to blame the defence. But look closely at how Milan concede: the goals originate from turnovers in midfield, with the back three already high and the midfield not yet dropped. That is a fault of the attacking structure, not the defensive line.

Amorim says he is willing to change. He says the team needs to "create an idea" but also needs to win. The tension between those two statements is the current weakness: Amorim's adaptation is reactive, not yet designed.

The clearest evidence is Diego Moreira. Against Lazio, Moreira came off the bench at half-time and scored a brace, rescuing a point. That is a positive signal about bench impact. It also raises an uncomfortable question: why is the best option always on the bench?

Bucharest did not collapse; it cracked open to reveal the human part the scoreline never records. I wrote that after France lost to Switzerland at Euro 2026, and I think it applies to Milan now. Three winless games do not destroy a project. They expose the parts not yet welded.

Christian Pulisic came on as a substitute against Benfica. No official reason was given — fitness management, rotation, or a tactical call. But if Milan keep lacking creativity near the box, Pulisic's status becomes a flashpoint. He is the profile who can receive between the lines, turn and open space — exactly the missing link.

Slow starts are becoming a pattern. Amorim admitted the first half against Benfica was not "in the game," and that it was the second consecutive match with first-half problems. That is mental preparation and game-plan territory, not just tactics.

Contrarian angle

The media narrative is running in an easy direction: Amorim is rigid with 3-4-2-1, repeating his Old Trafford mistake. I think that reading misses the core.

Reality is moving the other way. Amorim is not rigid — he is changing too often, too late, and too dependent on half-time. Moreira's brace against Lazio proves he can swing a match from the bench. But needing to swing it from the bench every week proves the starting plan is not working.

The insult from 2026 still echoes, but now I hear it as a sad song that needs rewriting. Back then they told me to go outside the press box and record fan reactions, leaving tactics to others. Eight years later I sit at San Siro and realise the stands are the earliest indicator of what the analytics will say three weeks later.

The bigger worry for Amorim is not the shape. It is that he is being judged by a yardstick he does not control: the player profiles at his disposal.

Transfer season is a rhythm check: who keeps the beat, who loses it, who changes it for a shirt. Milan are currently in the second group. When you need a No.10 who can hold the rhythm in the inside channel and you have nobody of that profile, changing shape only moves the fault from one position to another.

It also needs saying: three winless games against Juventus, Lazio and Benfica is not a disaster. Those are strong opponents. The problem is the manner. A 2-0 home defeat in Europe, after trailing by two for the second straight match, after losing first-half control entirely — that is what raises pressure.

What to watch

A familiar stand never sings the same song; be patient enough to hear the new rhythm. San Siro whistled this week; next week it may applaud. What interests me is not the volume but the beat.

Three signals over the coming rounds. First, the starting XI: does Amorim stay with 3-4-2-1 or shift to 3-5-2, or even a back four in-game? Second, the timing of concessions: if Milan concede in the first half again, the problem has left the tactical realm. Third, Pulisic's minutes: if he starts and plays beyond sixty minutes, box creativity changes significantly.

Amorim still has time. He has been in the job two months. But at Milan, two months can feel like two years elsewhere.

If the next result does not improve, the narrative shifts from "adaptation period" to "early crisis" within a week. And when that happens, nobody will remember that Milan paid for a Europa League place with the very lack of squad depth they now complain about.

I will be there next match, still in row eleven. And I will record the first half, because at San Siro the first half always tells the truth better than the final score.