Amorim’s Evaluation Period Lands AC Milan in a Late-Window Mess: The Cost of Buying Time

FolioPitch.com – 14 August 2026 | As the summer transfer window draws to a close, AC Milan finds itself in a precarious situation. The cost of buying time, as described by the club’s evaluation period under new head coach Ruben Amorim, has landed the Rossoneri in a late-window mess. With less than two weeks to go before the season opener, Milan’s mercato has come screeching to a standstill, leaving fans and players alike in a state of unease.

The evaluation period, which began with the signing of Mario Gila from SS Lazio on July 10, was meant to give Amorim a chance to assess the players currently part of the squad. However, it has now become clear that the Portuguese coach’s doubts centered around players who were all too predictable. Amorim wanted to study the likes of Pervis Estupinan, Yunus Musah, Ruben Loftus-Cheek, and Fikayo Tomori, rather than Strahinja Pavlovic and Alexis Saelemaekers, who were expected to be cast-offs.

The issue lies in the fact that the players deemed surplus to requirements are those who have routinely failed to impress over the past few months or even years. It is surprising that Amorim, who is known for his studious preparation, could not see what was coming, especially with a more demanding style. The old saying that a new manager brings a clean slate for everyone is perhaps fair to a degree, but it means that Amorim needs to form a complete picture with limited time available.

The experimental sides fielded in the first three preseason friendlies jeopardized the performances and results, and after the Celtic, Inter, and Chelsea games, Amorim has arrived at a very obvious conclusion. 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. There are some omissions from that list which might have seemed obvious candidates, like Yunus Musah and Ruben Loftus-Cheek.

The list of players to be sold is a clear indication that Milan’s summer window has come to a standstill. The club now has just one preseason friendly left, against Manchester United in Poland on Saturday, and it seems that the time for experimentation is over. Ruben Amorim will send out a strong side to face his former club, but 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.

There are a couple of emblematic cases that stand out. The first is Estupinan, who had a concrete offer from Aston Villa a few weeks ago, but Amorim vetoed the sale. That money has now vanished, all while the Ecuadorian has been deemed inadequate after all. The other is Nkunku, who was expected to be a good match for what Amorim wants, given that he showed his best in a high-pressing RB Leipzig team. Only now, 10 days before the Torino game, he is not a fit.

The mass cull of players is a key motive behind 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. 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.

The time for experimentation is over, and it is time for Milan to get back to business. The cost of buying time has been high, but it is not too late to turn things around. The question is, can Amorim and the Milan hierarchy deliver a late-window mess that will propel the team to success?