Oosterwolde back in focus as Roma assess fitness condition

AC Milan are emerging as frontrunners ahead of Roma in the race to sign Real Madrid's Endrick, with signs increasingly pointing towards the Rossoneri as favourites for the deal. Both Serie A clubs showed interest in the attacker during the summer, but Milan's position appears to have strengthened significantly in recent weeks. Roma may have an opportunity to discuss a potential deal with Real Madrid when the two clubs meet in the Champions League later in the month. However, La Gazzetta dello Sport report that Milan have strong structural advantages in their pursuit. The club's RedBird ownership maintains a good relationship with Endrick's representatives at RocNation, with Gerry Cardinale himself close to the agency that would facilitate any transfer. AC Milan and Roc Nation have been united since 2020 in what was described as a "unique partnership, driven by innovation, community, integrity, and inclusion", according to the official announcement of that deal. Milan and Real Madrid have also demonstrated a friendly working relationship in the past, having previously completed a move for Brahim Diaz. Should Los Blancos require assistance with Endrick's further development, circumstances could prove favourable for the Rossoneri. Milan may also soon face challenging news regarding the fitness of Alexis Saelemaekers.

Manu Koné could have left Roma in the summer transfer window after Chelsea made a late move for the French midfielder, but head coach Gian Piero Gasperini blocked the transfer. Arsenal and Manchester United had also shown initial interest, but Gasperini was determined to keep Koné as a key part of his squad. The midfielder has since justified that decision with strong performances in the opening weeks of the season, including a brace against Inter and recent appearances for France. Gasperini has now spoken publicly about why the Chelsea deal did not materialise. "There wasn't enough time. Also because these transfers involve bringing in a lot of people, even just to draft contracts," he said. The coach backed Koné to improve further, which he believes will raise his value in the coming months. "He'll have plenty of time to increase his value, even if he's already done so." Gasperini also acknowledged the backing of the Friedkin Group, Roma's owners, in keeping Koné at the club despite the opportunity to sell. "I feel the Friedkins' support, even though they're far away and rarely come to Rome. Galantic is here, but my goal is to bring them closer together." The midfielder's form suggests Koné will prove crucial to Roma's Serie A title challenge this season.

Endrick is among Roma's priority targets for the January transfer window after lengthy speculation over him during the summer. The Brazilian striker remains deeply unhappy with his situation at Real Madrid despite choosing to stay with the club, having received only four minutes of action against Elche under Mourinho's management. During the international break, Endrick's representatives held talks with Real Madrid's hierarchy to reiterate their frustration, but the club has made its position clear: no permanent sale will be entertained. Roma and AC Milan are both positioned to pursue a loan deal, the only avenue currently available. Several Premier League clubs, including Arsenal and Tottenham, have registered interest but are unwilling to consider a loan arrangement. AC Milan already attempted to bring Endrick to Italy during the summer, a fact confirmed by Pato in an interview at the Festival dello Sport. The Serie A remains one of the most concrete and attractive destinations for the player in January, and Roma have the strongest chance of securing him on loan. Gasperini is pushing for Endrick's arrival, and Roma's director D'Amico is actively working the deal. The coming weeks are expected to bring significant developments in the pursuit of the 17-year-old forward.

Gian Piero Gasperini is already planning Roma's January window despite the club sitting top of the table with a functioning attack led by Dybala and Malen. Between appearances at the Trento Festival and work at Trigoria, Roma are targeting reinforcements in the attacking department, focusing on players currently struggling for minutes at their clubs. A conversation between CEO Galantic and Gasperini at the festival underscores Roma's philosophy of planning winter moves in advance. Roma's priority remains a quality wide forward, with evaluation also ongoing into a more complete profile like Oosterwolde. Four players already tracked in the summer transfer window remain in the club's sights: Gittens, Leweling, Luiz Henrique and Endrick. The common thread linking them is a shortage of regular playing time. Gittens, a Gasperini favourite, has yet to debut in the Premier League. Leweling plays only sporadic minutes at Stuttgart and was excluded from the initial squad list under new national team coach Klopp. Luiz Henrique remains blocked in Russia by bureaucratic issues that have also cost him national team call-ups. Endrick's situation is the most delicate. Mourinho secured him at Real Madrid over the summer, but the Brazilian has virtually disappeared: just four minutes across La Liga and the Champions League combined. That picture of underuse could shift as soon as November, when UEFA will make decisions on the Settlement Agreement, opening new scenarios potentially favourable to Roma heading into the winter market.

Head coach Gian Piero Gasperini is pressing Roma to strengthen their attacking ranks in the January transfer window, a priority that remained unmet during the summer. At the Festival dello Sport in Trento, CEO John Galantic was asked about a possible January arrival and responded: "Nice question." Gasperini immediately added: "Very nice." While the comment was partly tongue-in-cheek, it underscores the coach's determination to add an attacking winger, a position he had already requested in the summer window. Roma's focus remains on securing an attacking wide player, though the club has also considered a full-back option in Jayden Oosterwolde. Four names dominate the shortlist: Jamie Gittens, Jamie Leweling, Luiz Henrique and Endrick. A common thread links most of them — they are struggling for minutes at their current clubs. Gittens, reportedly among Gasperini's preferred targets, has not yet made a Premier League appearance. Leweling has accumulated only 146 minutes across Bundesliga, German Cup and Champions League competition for Stuttgart without starting a match, a lack of game time that also cost him a place in Jürgen Klopp's initial squad list as Germany's new national team coach. Luiz Henrique remains in Russia following bureaucratic obstacles that delayed Roma's pursuit last summer; the Brazilian has also lost ground in the national team setup, making a January reopening of talks less straightforward. Endrick represents a different scenario. The Brazilian was close to Roma in the summer before José Mourinho chose to retain him at Real Madrid. The Portuguese manager had praised him publicly, but has given him only four minutes across league and Champions League fixtures so far. Should his situation remain unchanged, a loan move could become realistic in January. Financial constraints will prove decisive. UEFA's ruling on Roma's Settlement Agreement breach is due in November, and that verdict may constrain the club's negotiating room. Gasperini's technical priority is unmistakable — an attacking wide player — but the scope for converting that request into a concrete deal remains to be determined by the financial outlook.

Roma remain fixed on an attacking winger for the January transfer window, with four candidates dominating discussion at Trigoria: Leweling, Gittens, Luiz Henrique and Endrick. Head coach Gasperini is methodical in his approach—this is his familiar pattern, reshaping the squad when the window reopens. The club also has a full-back slot in mind, though a potential return to Oosterwolde cannot be ruled out. The winger target, however, commands the focus of sporting director D'Amico and Roma's recruitment team. Each of the four front-runners faces obstacles at their current clubs. Gittens, reportedly Gasperini's preference, has yet to debut in the Premier League and suffered an injury while on U21 duty. Leweling has accumulated only 146 minutes of action and missed selection in the new national team coach Klopp's initial squad of 44 players during a difficult phase at his club. Luiz Henrique remained in Russia due to bureaucratic issues and lost his international call-up, making a January move appear unlikely. Endrick, protected and blocked by Mourinho in summer, has been sidelined at Real Madrid with just four minutes of playing time granted. Much hinges on November, when UEFA will rule on Roma's alleged breach of the Settlement Agreement. The expectation is that a loan deal with a purchase option—a formula rejected by the club in summer—may now gain traction and suit Gasperini's requirements.