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Ruben Amorim has taken charge of three friendlies with AC Milan, and the work that remains to be done now seems obvious. La Gazzetta dello Sport write that Milan ‘suddenly themselves in deep trouble two weeks before their first competitive match’, with a squad to trim, reinforcements to identify and a playing philosophy to develop. In particular, in the game against Chelsea there were very few encouraging signs. Read SempreMilan ad-free and get access to exclusive news. Click here for a free trial! Pressing In the first three friendlies, everything has been pretty clear (at least, in intentions): compared to Milan under Allegri in 2025-26, this team has a higher centre of gravity by several metres and has one of its tasks being to win the ball back in the opponent’s half. The first 20 minutes against Inter showed what that can look like. Now, that’s the Milan that Amorim wants and seeks. At the beginning of August, against a strong opponent like the Nerazzurri, it’s not a given that it would succeed, especially for the entire match. Against Chelsea, it felt as though Milan’s press was disjointed and then evaporated completely. Even in the first half, against an opponent far from transcendental in ball movement, the Rossoneri never managed to get up the field and cause problems for the Blues. The attack Not that the derby had been a spectacular display, but at least some interesting plots from the defence forwards had been seen. This time, the Diavolo were nowhere to be found. Against their Premier League opponents they registered no shots on target, showing a complete inability to serve Francesco Camarda in the first half, and very little changed even with the introduction of Nkunku and Ramos in the second half. The team were more stretched this time than in the derby and took longer to make decisions on the ball. The attacking midfielders were never able to create, which is a worry. The defence Shivers of fear ran down the spines of fans tuning in to the match in Jakarta. It felt like we were back in May, or even worse, in the Milan of Fonseca and Conceiçao. The Rossoneri continued to concede goals largely through their own fault: individual errors, poor positioning, and poor runs. Anyone who attacks the Rossoneri’s rearguard, right now, has an excellent chance of creating a goal-scoring opportunity. Amorim is obviously giving the defenders new tasks, but – aside from the tragic final month and a half of last season – how is it possible everyone has forgotten Allegri’s wise teachings? The wings It’s been known since Amorim was announced that the Portuguese coach loves to play through the flanks, which are essential to his tactical plan. The problem is that with the current squad, the flanks lack suitable players. The only player capable of ensuring quality in both phases is Alexis Saelemaekers. Otherwise, Samuel Chukwueze is showing all the (predictable) difficulties involved and Zachary Athekame wasn’t even considered. Then on the other side Pervis Estupinan has reiterated his usual shortcomings when out of possession, and Davide Bartesaghi lacks the pace the coach requires to be direct. Mentality While the team had shown significant signs of a reaction up to this point (from 0-2 to 2-2 against Celtic, from 0-1 to 1-1 in the derby) this time, there was no response. Indeed, the first goal, scored in first-half stoppage time, was followed by five more in the second half. A flat line then followed after half-time and – even more seriously – a flat line for the rest of the second half. In essence, Milan never attempted to come back, or, more likely, were never capable of doing so.