Milan are preparing for the winter window with the intention of strengthening a squad built to return to the Champions League places and, in the shorter term, to compete for silverware this season. The club can register new players from 28 December and, unlike last January, expects to have funds available for targeted additions.
Last winter, with little room for investment, Milan addressed an attacking shortage by taking Füllkrug on a free loan. The approach has changed since then. In the summer, the club committed €150 million in transfer fees, excluding bonuses, on Ramos, Gila and Moreira, and the same principle is expected to guide the next window: players considered ready for Milan’s demands, with experience of major objectives and the character to become leaders.
Gerry Cardinale wants the club back among Europe’s leading sides after two consecutive seasons outside the continent’s elite competition. January will not be treated as an opportunity for indiscriminate spending, particularly because leading clubs are reluctant to lose key players midway through a campaign, but Milan believe the group still needs work.
The defence did not receive another signing after the arrivals of Gila and Diawara in the summer, while Tomori was brought back into the fold. Saelemaekers’ injury, which will keep him out for several months, has added another issue for the coaching staff and directors to address.
Inacio remains the leading defensive objective
Gonçalo Inacio is again at the centre of Milan’s planning. The Sporting defender was among the club’s preferred summer targets, in an operation examined by the hierarchy and approved internally.
Amorim knows Inacio well from their time together at Sporting, where the coach helped establish him in the first team. The 25-year-old has since become club captain following Hjulmand’s departure, and he has started every match this season despite extending his contract until 2030 last December on improved terms.
Sporting did not reject the possibility of a sale when Milan made an offer worth more than €40 million near the end of the summer window. The Portuguese club’s position was that a replacement of the required level had to be found before any deal could proceed. That condition prevented an agreement then, but Milan believe the discussion could reopen in January.
Inacio is receptive to the prospect of Serie A. He has shown frustration at times this season, a period that included an own goal in the Champions League and another in domestic competition. He is also dissatisfied with his standing in Portugal’s national team: he continues to be selected, including for the most recent World Cup, but has not played since the beginning of June.
A left-footed centre-back, Inacio is valued for his work in possession and ability to start moves from the back, qualities Milan consider particularly useful. There are reservations over his aerial duels. He played in a back three under Amorim and is now being used in a four-man defence by Borges, where he appears less comfortable.
The outstanding question is Sporting’s timing. The Lisbon club could consider a January departure, but may instead prefer to keep their captain until the end of the season.
Brazilian option depends on Real terms
Milan are also monitoring a Brazilian player at Real, although that route would be shaped by the Spanish club’s preferred formula. Real would only consider a loan, potentially accompanied by a very high purchase option and a buy-back clause, along the lines of the arrangement used for Nico Paz’s move to Como.
The player has informed his representatives that he would welcome an experience in Serie A if he does not receive sufficient opportunities under Mourinho over the coming months. Cardinale’s relationship with Roc Nation is regarded as an advantage for Milan as they assess whether that opening develops.
The coming weeks will determine whether either situation can move from preliminary work to a deal. Milan’s winter strategy is clear: add quality rather than simply numbers, and make the squad more capable of carrying the pressure of a season in which a return to the top table of European football remains the wider objective.
