Arrigo Sacchi, the former coach, outlined Milan’s “three reasons for regret” arising from their recent activities in the transfer market. Since clinching the Scudetto in the 2021-22 season, Milan has struggled to regain their former prowess. Their transfer dealings have left supporters disenchanted, leading to widespread frustration with owner Gerry Cardinale and RedBird.

Last summer, Milan surprisingly offloaded local favourite Sandro Tonali to Newcastle United, and the decision to part ways with Paolo Maldini also stirred concern among fans. Many felt Maldini advocated for a more ambitious and less financially driven project.

Although Milan made significant investments in the summer transfer window, their activity in the recent market was relatively subdued, failing to secure a new center-back or striker despite expectations.

In his analysis for La Gazzetta dello Sport, Sacchi scrutinized Milan’s transfer strategies, pinpointing three specific instances where they faltered.

“The impressive performances of Brahim Diaz with Real Madrid in the Champions League, Charles De Ketelaere’s consistent growth at Atalanta, and Calhanoglu’s pivotal role at league leaders Inter represent three undeniable regrets for Milan. These players, once donning the Rossoneri jersey, departed for various reasons. Additionally, Kessie, who recently triumphed in the Africa Cup of Nations, and Paqueta, a permanent fixture for Brazil, could be added to the list.”

“However, Kessie, while contributing significantly during Milan’s Scudetto-winning campaign, may not warrant the same level of acclaim. His desired move to Barcelona hasn’t lived up to expectations.”

“The situation with Diaz is straightforward. When Real Madrid sees potential in a loaned player, it’s only natural for them to recall him. Ancelotti noted Diaz’s substantial growth during his time in Italy.”

“De Ketelaere’s case requires a different perspective. Despite struggling initially with Milan, he has thrived at Atalanta, validating Maldini’s belief in his potential.”

“We must exercise patience with foreign talents, as integration takes time. Italian expectations often demand immediate results.”

“Lastly, Calhanoglu represents perhaps the most significant regret. He has evolved into an exceptional playmaker at Inter, showcasing character, vision, and a formidable shot. His contributions for Milan are undoubtedly regrettable.”