Milan underwent a major revamp over the summer following a troubling defensive performance in the 2022/23 season. The club welcomed a wave of new signings aimed at rejuvenating their chances for the Scudetto, marking one of the liveliest transfer windows in the post-Silvio Berlusconi era at the San Siro.
What initially seemed like a setback when Milan reluctantly sold Sandro Tonali to Newcastle United turned into one of the most exhilarating recruitment periods in the club’s recent memory. A total of ten new players joined the Lombardy side, sparking hope among Rossoneri fans for a potential comeback season.
While some fresh faces, such as Tijjani Reijnders, Christian Pulisic, and Ruben Loftus-Cheek, swiftly adapted and made an impact, others have struggled to meet the high expectations. Luka Romero and Marco Pellegrini are still in the early stages of their development, resulting in limited utilization by Milan coach Stefano Pioli.
Noah Okafor has displayed glimpses of his talent, yet injuries have disrupted his momentum. Aside from a disappointing performance against Lecce, Yunus Musah has had a relatively promising start in Serie A. These two players seem poised to be part of Milan’s future.
However, Milan may already be experiencing regret over two specific deals.
Samuel Chukwueze
Samuel Chukwueze’s future was a hot topic during the summer, drawing interest from several top clubs across Europe’s major leagues. Despite this attention, he opted to reject all offers and join Milan after an impressive five-year spell at Villarreal.
However, thirteen games into the new season, the 24-year-old winger has yet to contribute a goal or an assist. Is this reminiscent of Charles De Ketelaere’s situation? Milan invested significant time and resources in bringing Chukwueze to San Siro, much like they did with the Belgian forward.
Having dismantled defenses in La Liga for years, the left-footed winger arrived at Milan amid high expectations. Yet, his early days in Serie A have been far from successful. Whether it’s struggling with the language or coping with the pressure of playing for a top-tier team, Chukwueze’s initial performances have been disappointing.
Milan had high hopes for him, especially in the absence of Rafael Leao due to injury and Olivier Giroud’s suspension. Coach Pioli anticipated Chukwueze would showcase shades of his stellar La Liga form. Instead, he repeatedly lost possession, causing more harm than good against Fiorentina.
While there’s still room for a turnaround, his start at Milan hasn’t shown much promise.
Luka Jovic
Chukwueze is showing effort, unlike Luka Jovic, who played a role in Milan’s first-half victory on Saturday by setting up Theo Hernandez for the move that led to a crucial penalty. However, Jovic’s lackluster approach nearly became a setback for Milan when he missed a huge opportunity to secure a 2-0 lead, highlighting his poor finishing once more.
Let’s be honest—Jovic was brought in as a last-minute solution. As the transfer window neared its end, Milan couldn’t secure alternatives to Giroud; Mehdi Taremi wasn’t attainable, Jonathan David was too costly, and Divock Origi was already part of the club’s past.
Under the pressure of time, Milan hurriedly sealed Jovic’s arrival, an almost panicked decision. It felt off from the beginning, especially considering the Serbian’s struggles at Real Madrid and his similarly disappointing stint at Fiorentina. Perhaps loaning out Lorenzo Colombo was a misstep.
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