Who planned this? [Newsletter]

Did Milan wait too long? This has been one of the main questions since the Chelsea friendly at the weekend. While it was always going to look a certain way against a Premier League side (sadly), some players certainly failed to make the most of the opportunity, specifically those already on the brink.

Terracciano, Estupinan, and Loftus-Cheek fell into that category, to name a few, and we were simply reminded of why Milan have been unable to rely on them in the past. That brings us on to the dilemma at hand: the start of the season is now less than two weeks away, so why haven’t they been sold already?

It doesn’t have anything to do with a lack of interest, or an unwillingness to meet a high price tag for that matter, as Milan decided to keep them at Amorim’s disposal for the pre-season. The manager expressed a desire to test them all before making his final decisions and the Rossoneri obeyed.

That might sound like a reasonable plan on paper, but the reality is that you need to decide a lot earlier than August 10. Why? Because negotiations tend to take time, even if not always, and potentially selling more than ten players in just three weeks is a very difficult task. Especially since you also need replacements.

There might be the odd late-window opportunity, securing a player on a better deal than would have been possible earlier in the summer, but you can’t really do that over and over again. In other words, the Rossoneri could struggle with finding reasonable replacements even if the sales are completed. Perhaps they did wait too long…

My initial plan was to only discuss the season opener against Torino, scheduled for August 23, but that would have left out a pretty big piece of the story. After three friendlies without a win, Milan will have their final chance at clinching one against Man Utd on Saturday.

As said above, it’s never ideal to face top Premier League clubs if you want a near-enough guaranteed pre-season win, not to mention that Man Utd have found form under Carrick’s guidance. However, this takes the (negative) prize for a very obvious reason: Amorim’s past at the club.

He was ridiculed by the end of his tenure at Old Trafford, perhaps rightfully so, and it certainly put a blemish on his reputation (which was very good after the success with Sporting). I can only imagine that he wants revenge, even if a pre-season friendly doesn’t hold much pedigree, but that could easily backfire.

A defeat would not only lower Milan’s confidence ahead of the season opener, but it would also open the floodgates for Man Utd fans to voice their opinions. They have already said a lot about the Rossoneri’s pre-season, so there could be a lot more fuel come Saturday evening.

In short, I would describe this as potentially the worst possible pre-season finale for Milan. Mike Maignan and Adrien Rabiot won’t be there to help either as they have been granted additional leave, set to return on August 16 instead (what is that all about?!). The season hasn’t started yet, but we already need a break…

Below, we have collected the most important Milan news from the last week, including our longer reads and newspaper reports.

Last week, Milan Futuro faced Monza as part of their preseason preparations in a behind-closed-doors friendly, and it was quite a close game in the end. Sergio Navarro’s men can take great encouragement from the fact they twice led against the newly-promoted Serie A side, but ultimately they were beaten in a six-goal thriller.

Mike Maignan has found himself at the centre of a storm for a few reasons. Firstly, the captain was criticised for not attending the funeral of Franco Baresi. Then, the announcement that he and Adrien Rabiot have delayed their return to Milanello in order to extend their vacation did not go down too well either. It has led to talk Maignan could be sold, though there have already been denials.

As mentioned above, there are plenty of other doubts for Amorim to resolve in the final part of preseason before the 2026-27 campaign properly kicks off. It is expected he will name a strong XI for the final friendly to fully take stock of what he has, while also ironing out some obvious deficiencies and getting a further idea on what the squad needs.

Mercato round-up: an Atalanta wing-back is on Milan’s radar; there is competition to land Alphadjo Cisse on loan; Santiago Gimenez is getting closer to joining Porto; a Genoa defender has been offered to the management; Athekame is on the move and a Genk star has been named as a potential replacement; a mass exodus is being sought in the final three weeks of the window.

Our longer reads from over the past week include a look into the Rabiot-Maignan issue and what their delayed return really means, as well as three conclusions from the defeat to Chelsea, plus the tactical breakdown of that game and the one against Inter a few days prior.

Below, we have collected the bonus content from the last week. Remember, you can try seven days completely for free!