According to Portuguese media outlet Record, Benfica attempted to sign Estupiñán at the end of the summer transfer window, but Amorim refused.
During the summer transfer window that just closed, Estupiñán was at the center of transfer speculation. Aston Villa came close to signing him from AC Milan in mid-July, but Amorim halted the move because he wanted to assess the player during the preseason tour before deciding whether to allow his departure.
Reports from Portugal indicate that this South American full-back attracted interest from more than just English clubs throughout the summer. Benfica also made their move. Record reported that, especially in the final weeks of August, Benfica's management made several attempts to bring Estupiñán to Lisbon, but Amorim also refused. Amorim was unwilling to let Estupiñán leave because he considered the player crucial to his tactical system. Faced with the Milan coach's resistance, Benfica adjusted their left-back recruitment strategy and finalized the loan signing of Caruani with an option to buy before the transfer deadline.
Although Estupiñán was initially made available for transfer after a disappointing first season at Milan—with his winning goal in the second leg of the derby being one of the few bright spots—after working with him for several weeks, Amorim changed his mind and decided to keep him, believing the player fit his tactical requirements.
This is reflected in Estupiñán's involvement so far this season: the former Brighton player has started in 2 of Milan's 3 official matches, against Torino and Juventus respectively.
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