AC Milan remain in the market for a new wing back before the summer transfer window closes, despite prioritizing other positions in recent weeks. Manager Ruben Amorim’s tactical blueprint, unveiled during a 2-2 preseason draw against Celtic, has placed fresh emphasis on the importance of versatile, minded players in wide defensive roles.
Amorim’s approach represents a significant departure from Milan’s recent tactical setup. Gone are the deep defensive blocks of previous seasons, replaced by an aggressive pressing system designed to win possession high up the pitch. The new manager demands verticality in and rapid transitions into space, placing the wing backs at the heart of his tactical vision. Early evidence from preseason suggests the Portuguese coach is already making progress in implementing his philosophy at San Siro.
Samuel Chukwueze’s future at the club has taken an unexpected turn under the new regime. When Fulham expressed interest in acquiring the Nigerian winger last spring, offering around 24 million euros, Milan appeared ready to sanction the sale. Amorim’s arrival ced everything. The former Sporting CP manager sees untapped potential in converting Chukwueze from a traditional winger into a modern wing back, capable of exploiting space in the opposition half while maintaining defensive discipline. An assist for Francesco Camarda in the Celtic friendly provided encouraging early returns on this tactical experiment, prompting Milan to reject subsequent interest from Turkish side Trabzonspor.
While Chukwueze and Alexis Saelemaekers offer the one on one dribbling ss Amorim values on one flank, the manager seeks greater balance on the opposite side. Defensive solidity during transition phases remains a priority, particularly as Milan adapt to a more adventurous tactical setup. Davide Bartesaghi has emerged as a reliable option who could feature regularly, with the versatility to operate as a left sided center back when required. More intriguingly, Pervis Estupinan’s proposed move to Aston Villa has been placed on hold while Amorim assesses whether the Ecuadorian, whom he knows from their time together at Sporting, fits his current plans.
Should Estupinan’s departure eventually materialize, Milan have identified two potential replacements. Manchester United’s Noussair Mazraoui has caught Amorim’s attention, though significant obstacles complicate any potential deal. Questions remain about the Moroccan international’s willingness to accept a wing back role, while United’s openness to selling a player they only recently acquired remains uncertain. Raphael Guerreiro presents a contrasting option. The seasoned defender became available on a free transfer after his contract with Bayern Munich expired, bringing remarkable offensive production from defensive positions. His record of 42 goals and 47 assists across 223 Bundesliga appearances demonstrates the ing threat Amorim craves from his wing backs, though his age may raise concerns about longevity.
As preseason continues, Amorim’s tactical assessment will determine whether Milan enter the market before the window closes. Chukwueze’s successful conversion to his new role could eliminate the need for reinforcements, while Estupinan’s adaptation may provide the balance the manager seeks. Either way, the coming weeks will reveal whether Milan’s wing back positions require additional investment or if Amorim can extract maximum value from his existing resources. For a club rebuilding under new management, these decisions carry weight far beyond a single transfer window.
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