Welcome to Calcio Square, an email newsletter dedicated to Serie A and Italian football. Every Thursday, I dedicate my entire post to one specific theme or trend. Today's issue focuses on the toxic and increasingly unpredictable environment at AC Milan.

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There's nothing to like about AC Milan these days. Their best players are under-performing, the fans want the owner to skip town, and management has inspired zero confidence in their ability to recruit players. San Siro has become toxic and the football has deteriorated. Three coaches have tried to shock the players back into rhythm. None have had success.

There really is no going back when you criticize your players for lacking the basics. Head coach Sergio Conceicao admitted as much after Wednesday's 2-1 loss to Dinamo Zagreb in the Champions League. Thankfully, the result didn't eliminate the Rossoneri. But it seems to have had consequences.

The purge has begun. Alvaro Morata is reportedly close to joining Galatasaray. Emerson Royal is surely gone in the summer. Strahinja Pavolvic also answered questions about his future and has interest abroad. All but one of the four players Milan signed permanently last summer are on the market.

It's better to admit mistakes early than to persist with them and hope they somehow get corrected. Morata is quite clearly not the striker Milan need. The team is used to playing with a target man up front who can hold up play and finish chances. Morata — and to an extent Tammy Abraham, who is only on loan — is a space invader who presses well and battles but fulfills little of the traditional role of the center-forward.

But then, why sign him in the first place? Why place nearly €40M in wagers on Emerson and Pavlovic, the former being clearly subpar and the latter ill-suited to playing in a high line? Pavlovic is a man marker, a defender who likes to tango, and here he is in a team that does not man-mark or like to tango.

So then you wonder whether management has any idea what they're trying to build. They've made plenty of bets all over the field and had more misses than hits. Think about it: Milan have spent nearly €200 million since January 2023 and have only gotten worse. Yunus Musah, Samuel Chukwueze, Ruben Loftus-Cheek, and Noah Okafor cost a combined €77 million. Milan could've spent that on a couple of higher-quality players and raised the overall level of the squad. They could've kept Sandro Tonali and preserved a bit of what it means to play for Milan. Instead, they established a lower floor for standard performance.

I fear the club could be gambling more of its future on Feyenoord forward Santiago Gimenez, who's expected to cost around €40 million and has not yet played in a top five league. Of course, there is potential here as he's only 23 and has scored 64 goals in 104 total appearances for Feyenoord. Gimenez also more closely fits the prototype of the traditional center-forward. But it's so hard to judge Eredvisie strikers. For every Robin van Persie, there is a Vincent Janssen or Ricky van Wolfswinkel or Klass-Jan Hunteelar.

Then you see other potential moves on the horizon. Milan could sign Udinese's giant of a striker Lorenzo Lucca and send Francesco Camarda out on loan. Fikayo Tomori could leave. Davide Calabria has interest. So many things could happen in just a few days. And we are days away from deadline day.

It's not especially reassuring to see a club change so much in January. But then, these changes may not even be enough to salvage the season.