Aston Villa made two attempts to sign Pervis Estupiñán from AC Milan before the summer transfer window closed on 1 September, according to Sport Witness. Both approaches were ultimately blocked by Milan head coach Ruben Amorim, who preferred to keep the Ecuador international for his own tactical plans.
The outlet reports that Villa appeared close to an agreement early in the window, with Estupiñán keen on a move to the Premier League. Amorim intervened, however, wanting to test the former Brighton player within his back-three system during pre-season. A second attempt later in the window met the same resistance, with Milan also turning down interest from Benfica.
With the Estupiñán route closed, Villa moved for Matteo Ruggeri instead. The new arrival has already made his debut under Unai Emery, settling the left-back position that the club had sought to strengthen throughout the summer.
Italian commentators have since questioned Amorim's stance. Journalist Alfredo Pedulla described the decision to retain Estupiñán as reckless after the defender was caught out during Milan's recent 2-2 draw with Lazio. Pedulla noted that the South American appeared unaware of runners behind him, a recurring issue in Serie A.
Francesco Letizia added that blocking the Villa transfer made little financial sense for Milan, given the club's broader strategy of mixing established stars with younger players. She argued that Estupiñán fits neither category, suggesting a sale would have freed funds for a more suitable replacement.
Estupiñán has started two league matches for Milan this season but is yet to look comfortable in Amorim's structured setup. His most effective football came previously under Roberto De Zerbi at Brighton, where he was encouraged to attack open spaces rather than hold rigid positions.
No Premier League club can now complete a signing until the January 2027 window opens. Villa's focus remains on integrating Ruggeri, whose arrival rendered the Estupiñán pursuit a closed chapter of the summer business.
