"If Not Now, When?" Primo Levi asked himself in a well-known novel. Ruben Amorim’s aim may not be as noble as that of the famous Turin-born writer, but there is a reason behind it. On the day he took charge of Milan, the Portuguese coach announced that he wanted an attack-minded team, one always eager to dictate play and dominate matches. In Serie A, however, the need to maintain balance has often clipped the wings of even the most attack-minded coaches.
For example, Amorim himself has never started a match with two out-and-out attacking wingers such as Chukwueze and Moreira. The Belgian, who has scored three goals in his last two league appearances, has instead been used as a (deadly) weapon off the bench, as pointed out via 'La Gazzetta dello Sport'.
Alexis Saelemaekers’ injury now forces the former Sporting and Manchester United coach to face a difficult dilemma as early as the next match against Sassuolo, on Sunday at 6 p.m.: should he really start Moreira or Cisse and field four attacking players, with Modric and Rabiot in central midfield, or should he devise a more cautious solution, perhaps moving the Frenchman out to the left and bringing either Jashari or Musah into midfield?
Milan, back to training...
As early as today, when Milan regroup at Milanello following the day off granted by Amorim, we may get a clue as to the answer. The last players returning from international duty, including Modric, Jashari and Musah, will also be back, bringing the squad up to full strength apart from Saelemaekers and possibly Estupinan.
The medical staff, however, remain fairly optimistic about the latter. Despite the injury he sustained while on international duty (a mild knee sprain), there is hope that the Ecuadorian can recover in time. If Amorim does not want to risk him, Davide Bartesaghi is ready to step in.
Barring any surprises, the Rossoneri coach should continue along the path he took in the final match before the international break against Lecce. That means moving away from his trademark 3-4-2-1 formation in favour of the 4-2-3-1, which allows Chukwueze to track back a little less defensively.
As mentioned, the gap to fill compared with the victory over Lecce is on the left wing. Saelemaekers provided versatility in both attacking and defensive phases, but Milan do not have a similar player in their squad.
Based on his characteristics and current form, the choice should therefore fall on Moreira, who has started just once, away to Juventus in Turin. Not coincidentally, that was the only match in which Chukwueze was not included in the starting lineup.
That is why, if Amorim were to field an attacking midfield trio of the Nigerian, Pulisic and Moreira behind Gonçalo Ramos, we would be looking at the most attack-minded version of Milan in the 2026–27 season. And the situation would be no different (quite the opposite, in fact...) if Cisse were preferred to the Belgian.
Risks and Caution
It would be an intriguing, and perhaps dangerous, gamble to use this lineup against a team as adept at counterattacking as Sassuolo. Juventus know something about that, having left the Mapei Stadium badly bruised a few weeks ago.
The injury situation, however, does not leave Amorim with many alternatives, apart from completely reshaping the midfield by starting Jashari alongside Modric, or Musah alongside Modric.
The Swiss midfielder has started all four of his national team's last four matches. He has not played this much since his time at Club Brugge.
The American, meanwhile, is the Milan player who has covered the greatest distance by air during the international break, which is why his physical condition will need to be assessed in the days leading up to the match.
In that case, if Milan stick with the 4-2-3-1, Rabiot would operate on the left flank, a position he has already played under Massimiliano Allegri at Juventus. Alternatively, he could occupy one of the two attacking midfield positions if Amorim decided to return to the 3-4-2-1.
Loftus-Cheek also remains an option in the background...
Of all the possibilities, however, the ultra-attacking version featuring four attacking players is the most enticing.
If not now, when?
