Amorim's Milan: The Crack Sits in the First Phase of Possession

Europa League night at San Siro, and Milan lose 2-0 at home to Benfica. It is the third match in a row without a win for Ruben Amorim's side, and the second consecutive match in which they have fallen two goals behind. The stands went quiet from the middle of the first half, as the home side's build-up kept circling in front of the box before being snapped off. Benfica goalkeeper Trubin did not have to empty his tank, and that detail is what kept me in my seat longer than usual after the final whistle.

I have followed Milan since the years I spent in Madrid writing for Báo Thể thao Thế giới, long enough to be used to a big club losing because of missing players, a loss of form, or a referee's call. This was different. This team lost while holding the ball.

The setting: a two-month project and a fixture list that was never easy

Amorim took the Milan job in June, at a point when the club returned to European competition after a season away. That return is a plus in broadcast revenue, matchday income and media pull. It also creates double pressure: a club back on the continental stage is expected to hold a Champions League place in Serie A while also going deep in the Europa League.

Milan's last three matches read: draw with Juventus, draw with Lazio, defeat to Benfica. Look at the names and nothing looks alarming. Juventus and Lazio both belong to the group competing for European places in Serie A, and Benfica are a familiar Portuguese representative. What is alarming is the way those matches unfolded. Two matches in a row, Milan fell two goals behind. In both, their first half barely existed as a shape.

Amorim himself admitted it after Benfica: his team in the first half was not really in the game. He said plainly that this was the second consecutive match with first-half problems. For a coach heavily criticised in England for being seen as too rigid with the 3-4-2-1, raising mental preparation and match-planning as the issue is a calculated move: it shifts the story away from the shape and towards the opening phase.

Core analysis: the problem sits in the first possession phase and in the turnover phase

The line that stopped me longest was Amorim's remark that Milan create more problems for themselves when they have the ball than when the opponent does, and that their turnovers happen in positions dangerous to their own goal.

To me that is a precise description of a structural fault, and the fault lives at two specific moments in the passing chain. The first is the initial build-up from the back three. When the midfield does not create a clean triangle to escape through, the centre-back is forced to go long or push the ball wide to a wing-back already marked. The second is the reaction after losing the ball. The space behind the two central midfielders in a back-three system is wide, and if the two inside number tens do not drop in time, one vertical pass is enough to reach the opponent's build-up zone.

Then comes the third issue, the heaviest of the three: creativity near the box. Amorim admitted the team lack creativity around the penalty area and are not creating enough, even though the staff have tried to build routines aimed at getting the ball into the box more often.

Two things need separating. Poor finishing can be a consequence of creating few chances, but a team that creates chances always leaves data to analyse. Milan are not giving me that kind of data yet, so I cannot push this onto finishing. This is a coaching problem and a personnel problem.

The 3-4-2-1 demands two wing-backs with the engine to run the flank continuously, and two inside number tens who know how to open space through off-ball movement. In that system, creativity does not come from one player beating a man; it comes from several players being in the right place at the same time. Miss one of those two groups and the whole structure goes dark in the final thirty metres.

Based on my experience watching matches live in Serie A and the Europa League this season, the clearest signal is not the number of goals conceded but the tempo of the escape. The team is moving the ball a beat slower than the system requires, and that slow beat turns every sideways pass into a counter-attacking chance for the opponent.

That is why Christian Pulisic's place on the bench deserves attention. I do not have enough data to conclude whether it is a tactical decision, fitness management or simple rotation. But when a side short of creativity near the box starts a match with one of its most creative players on the bench, that fact has to be laid next to the technical problem above. Since the 2026 data rebellion, I stopped trusting numbers and started trusting the way they are placed next to each other.

The rare bright spot came from the bench. Diego Moreira came on at half-time and scored a brace in the draw with Lazio. Credit where it is due: it shows Amorim can influence a match from the technical area, and that this squad has a substitute who knows where the goal is.

But a player scoring twice after coming off the bench is also a reminder: the first-half problem remains unsolved. You can win one match with a half-time correction. You cannot win a season that way.

The contrarian angle: the official story is hiding a blind spot

The prevailing narrative in Italy is easy to guess: rigid back three, conservative coach, team not yet adapted. I think that explanation is convenient and wrong.

First, a back three does not by itself produce turnovers in dangerous areas. Plenty of teams play with three centre-backs and still control the ball safely. The issue is the distance between the lines and the ability to defend forward immediately after losing the ball.

Second, the comeback against Lazio is being told as proof of character. To me it is also proof that the starting eleven was chosen wrongly. A coach who fixes a match at half-time is usually a coach who set it up wrong from the start. And you cannot spend a substitution every match to rescue a first half.

Third, and this is the least discussed part: in the transfer market, a club switching to a back three has to buy the right profiles — wing-backs, inside number tens, a striker who can hold the ball. Those profiles are scarce and expensive, and their prices tend to be pushed up precisely when a big club is in a hurry. In 2026, when PSG triggered Neymar's €222 million release clause and split the payment across instalments, the whole market understood that the sticker price is only the visible layer of the story. In the data I hold on Milan right now, there is nothing on budget, wage bill or contract length. When data is missing, the right move is to record the dates that need verifying, not to construct a plausible-sounding conclusion.

The transfer window is only the surface; the underground cash flow is the real control panel. And a contract does not create an era; an era creates the contract.

There is one more detail worth placing alongside the rest. Amorim has been in the job two months. He reminds people of it when he talks about the work done so far. That two-month window is real, and it belongs to the case defending him. But two months is also long enough for a squad to show a structural problem. Time is a valid shield with the media; with the league table it carries no weight.

For a club just back in Europe, the most damaging thing is not the two goals conceded. It is conceding first in two consecutive matches, because that forces the team to play a kind of football they have not finished training for.

What to watch

I am not making a prediction here, only recording the markers to check. The first thirty minutes of the next match will show whether Milan have fixed their entry into games. The starting shape and the ability to shift to a 3-5-2 or a back four mid-match will show whether Amorim's adaptation is real or rhetorical. Pulisic's minutes will show how the creativity problem near the box is being handled. And Moreira's role — start or bench — will show whether the bench is a tactical solution or a blanket over a hole.

I have watched more projects than I can count begin with the phrase we need more time. Some succeeded. Most of those succeeded because the club fixed the structure, not because time passed on its own. Age 59 taught me one thing: every summer there is a truth buried under hundreds of headlines. With Milan, that truth is sitting in the very first touches of each half.