Former coach Arrigo Sacchi explained why Milan have ‘three reasons for regret’ following their recent work in the transfer market.

The Rossoneri have struggled to recapture the magic since winning the Scudetto in the 2021-22 season, with their work in the transfer market upsetting the supporters, leading to much frustration with owner Gerry Cardinale and RedBird.

Milan unexpectedly cashed in on local hero Sandro Tonali last summer, selling him to Newcastle United, and their decision to sack Paolo Maldini also generated concern amongst fans, with many believing the former defender was pushing for a more ambitious and less financially focused project.

The Rossoneri did spend fairly heavily in the summer transfer window but were far quieter in last month’s market, not bringing in a new centre back or striker despite hopes.

Writing for La Gazzetta dello Sport, Sacchi analysed Milan’s work in the transfer market, highlighting three specific examples where they went wrong.

“The wonder of Brahim Diaz with Real Madrid in the Champions League, the constant growth of Charles De Ketelaere with Atalanta, the increasingly decisive role of Calhanoglu with league leaders Inter.

“These are three reasons for regret for Milan, there’s no doubts about that, because they were Rossoneri players who, for one reason or another, left. To these, if desired, we could also add Kessie, who has just won the Africa Cup of Nations, and Paqueta, who plays permanently with Brazil.

“The last two elements mentioned, however, in my opinion don’t belong to the larger category. Kessie has a lot of strength, a lot of determination, he was useful to Milan in the Scudetto season, but he doesn’t seem like a phenomenon to me and at Barcelona, where he wanted to go at all costs, I don’t think he’s enchanted me.

“On Diaz the matter is quite simple. If Real Madrid lend you a player and see that he is improving and can be useful to them, it’s logical that they’ll take him back. Ancelotti explained to me that he has grown a lot in Italy, also from a physical point of view.

“It means that at Milan they worked well on him. The reasoning to be made about De Ketelaere is different. He is playing very well for Atalanta, after a difficult season with the Rossoneri. This means that Maldini was right, he had wanted him at all costs and considered him a potential champion.

“The fact is that you need to be patient with foreigners, and instead us Italians always demand the best without giving them time to integrate.

“Finally, Calhanoglu is a real regret, perhaps the biggest. He’s proving to be a regista of the highest level. At Milan he played as an attacking midfielder, at Inter he is the playmaker and is at the centre of the move.

“He has character, vision of the game and a precise and powerful shot. Yes, for Milan he is to be included in the list of regrets as well.”

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