The cost of buying time: Amorim’s evaluation period lands Milan in a late-window mess

Thursday August 13 is being billed as a kind of ‘D-Day’ for AC Milan’s 2026 summer transfer window, with the ‘D’ meaning decision.

Rewinding just over one month to July 10, Milan had just announced the signing of Mario Gila from SS Lazio. It was their second acquisition of the summer after the club-record deal for Goncalo Ramos from Paris Saint-Germain, and took the spending to around €100m just a few days into the window.

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At the time there was talk of ‘more to come’, with Gerry Cardinale having finally put his foot down on the accelerator, both to back the head coach he chose – Ruben Amorim – and also to mark the fact that RedBird Capital were sole proprietors, after the Elliott Management vendor loan was paid off.

Fast-forward from there to today, and not a lot has happened since. A quiet period was natural as the World Cup concluded, but we now sit 10 days away from the season opener and only the young Sankhoun Diawara has arrived since.

Part of the reason for this is Milan’s complete inability to sell players that are not part of the plans, and part of the reason for that is also down to the coach needing to decide who actually has a role in the project. All this has seen concern evolve into frustration and worry over a four-week period.

Asking for time

On the face of things, there is categorically nothing wrong with a new head coach wanting a period of evaluation to assess the players currently part of the squad. Only up close can a manager truly see what he is working with, so that aspect is fair enough.

It’s not like this was ever going to be a hand-in-glove fit, either. Milan last season did play with three centre-backs and wing-backs last season, but Massimiliano Allegri’s 3-5-2 could not be further from Amorim’s 3-4-2-1 from a philosophical point of view.

So, while there are players that many fans instantly presumed would become deadwood, it is probably right that Amorim applied the handbrake and chose to study a bit more carefully. After all, a new internal resource means less money needing to be invested in that particular spot.

The issue is two-fold: personnel and time. Regarding the former, the concerning thing to many fans is that the Portuguese’s doubts seemed to centre around players that were all too predictable. Amorim wanted not to assess Strahinja Pavlovic and Alexis Saelemaekers, but Pervis Estupinan, Yunus Musah, Ruben Loftus-Cheek and Fikayo Tomori.

The ones that needed to pass an audition were players that had routinely failed to do so over the past few months or even years. Surely Amorim – who is very studious in his preparation and reportedly watched a lot of Milan games from last season – could have seen what was coming, especially with a more demanding style.

The old saying is that a new manager brings a clean slate for everyone, and that is perhaps fair to a degree. Yet, what that means is the need to try and form a complete picture when there is far from infinite time available.

So, Amorim fielded experimental sides in the first three preseason friendlies, which in itself jeopardised the performances (there is a need to assimilate his ideas and build chemistry quickly) and the results. Moreover, after the Celtic, Inter and Chelsea games, he has arrived at a very obvious conclusion.

Indeed, according to the latest from Sky, the players that are outside of the coach’s plans and that Milan aim to sell this window are as follows: Tomori, Youssouf Fofana, David Odogu, Christopher Nkunku, Filippo Terracciano, Santiago Gimenez and Pervis Estupinan. Are there any shocks there?

Now, of course there are some omissions from that list which might have seemed obvious candidates, like Yunus Musah and Ruben Loftus-Cheek. Opinions on those players aside, it can potentially be argued that Amorim has achieved what he set out to: he has two added options that might have otherwise ended up on the scrap heap.

As we stand at present, though, there is an understandably uneasy feeling that there is an almost deliberate force behind the fact that Milan’s summer window came screeching to a standstill.

Running out of runway

Milan now have just one preseason friendly left, against Manchester United in Poland on Saturday. It seems that the time for experimentation is over, and that Ruben Amorim will send out a strong side to face his former club. It’s about time, too.

While that game goes on, that aforementioned list of players will be glued to their phones waiting for potential news from their agents. They may well even be left out of the fixture altogether, leaving a reduced travelling squad.

Here the calendar becomes Milan’s enemy once again. Selling players is difficult at the best of times, especially when it has become public knowledge that these are cast-offs not deemed good enough for a club that collapsed in dramatic fashion last season.

Things do tend to accelerate as deadline day draws closer, but let’s be honest here: the chances of Milan offloading every single name out of the seven mentioned is virtually zero. To secure landing spots for even some of them it is likely that loan formulas with deferred or even non-guaranteed buy-outs will be needed.

There are a couple of emblematic cases that stand out. The first is Estupinan: Aston Villa came in for him a few weeks ago, with Unai Emery keen on a reunion. A concrete offer was made, Amorim vetoed the sale, and so they have turned elsewhere. That money has now vanished, all while the Ecuadorian has been deemed inadequate after all.

The other is Nkunku. All preseason we have heard about how the Frenchman should actually be a good match for what Amorim wants, given that he showed his best in a high-pressing RB Leipzig team, and in theory is perfect for one of the playmaker roles. Only now, 10 days before the Torino game, he now isn’t a fit.

Then there are the ‘other’ cases to resolve, above all the Rafael Leao saga that has rumbled on in the background since those comments before the World Cup. The Portuguese’s fate has gone from certain departure to a potential mission to rebuild the bridges that were burned. From a tactical perspective he is factually less suited to Amorim’s style than Nkunku, so what exactly is going on?

One of the key motives behind the mass cull one presumes is the desire to welcome further reinforcements to the squad. Another centre-back, wing-back, attacking midfielder and maybe even central midfielder are being targeted. Just like with the sales, that is a lot of business to do in less than three weeks.

So, while it might feel as though the handbrake has finally been released and Milan’s mercato can spring back into life, the hourglass never stopped and the time kept ticking buy. Without a late flurry of sensible business, there is a real risk of Amorim going into an already-challenging role with a bloated yet incomplete squad.