Jayden Oosterwolde

Roma's pursuit of Real Madrid forward Endrick remains at an impasse two months after a summer rejection, with the Spanish club offering neither discussion nor closure on a potential move. The international break has revived interest in the 20-year-old, who has made only four minutes of league action and no Champions League appearances under Carlo Ancelotti and remains keen to leave in search of regular playing time. Endrick has repeatedly told Real Madrid he wants to join Roma and wear the giallorosso, most recently reiterating this to José Mourinho before reporting to the Brazilian national team two weeks ago. Ancelotti has publicly acknowledged the forward needs consistent minutes to develop. Head coach Gian Piero Gasperini has not prioritised the signing, concentrating instead on upcoming fixtures rather than transfer activity—a perspective that makes sense given the January window lies three months away. Roma's primary target remains a winger with specific qualities: physically strong and capable of explosive pace. Endrick is not that profile, though Gasperini would accept him as a secondary option, potentially deploying him on the right wing or as a second striker. The first-choice targets remain Chelsea's Gittens, Stuttgart's Lewelling and Zenit's Luiz Henrique, all of whom were discussed in the closing stages of the summer market and remain on Roma's radar. Only Henrique received significant playing time after negotiations halted in August. Another barrier exists: the Friedkin family's likely demands for departures before any arrival. Soulé has been repeatedly pursued—both in summer and now through the winter window—while a possible move for defender Oosterwolde could mean Rensch or Ghilardi leaving. Oosterwolde was abandoned at the end of August due to physical problems, which are reportedly now resolved. For any Endrick deal to progress, Real Madrid must break its silence, the player must remain committed despite minimal minutes, and Roma must find clarity on squad-trimming priorities.

Roma could reopen talks with Jayden Oosterwolde during the winter transfer window after a summer move collapsed over medical concerns. The club had scheduled the defender's medical examinations before completing the deal, but assessments revealed a significant muscle tear that required surgery and an estimated three-month recovery. Roma chose not to proceed at that point, but have kept the 2001-born left-back on their radar. Director of sport Massimo D'Amico continues to monitor Oosterwolde's progress, and head coach Gian Piero Gasperini had already approved the move when it was being considered in summer, signalling how highly the former Parma player was valued for the project. The failed summer operation has not damaged relations between the parties. Roma will reassess Oosterwolde once he returns to full fitness and provides sufficient physical guarantees, with the January window offering a chance to revive negotiations that seemed all but done before the injury setback. A recent sign of sustained interest came during Roma's Champions League fixture against Istanbul, when Oosterwolde greeted several Roma players and subsequently held talks with Gasperini and his staff. Much will depend on the Dutch defender's recovery and Roma's own evaluation, but he remains a profile to watch for the giallorossi's left flank.

Roma's interest in Jayden Oosterwolde has not ended despite the dramatic collapse of negotiations last summer. The Dutch player arrived in the capital for medical examinations, but concerns emerged over his muscle injury during those tests. In early September, he underwent surgery with a recovery period estimated at around three months. Director Tony D'Amico and head coach Gian Piero Gasperini have kept Oosterwolde on their radar, with January potentially offering a second opportunity to complete the deal. Gasperini had already approved the move in summer, and both he and D'Amico continue to monitor the player's rehabilitation. The club has not crossed Oosterwolde off their list and remain interested in the former Parma player once he returns to full fitness. A recent encounter in Istanbul before Roma's match against Fenerbahçe showed the relationship remains intact: Oosterwolde greeted several Roma players and met with Gasperini, the medical staff and the fitness team. Roma are watching the progress of his recovery without urgency but without having closed the door either. If his physical condition provides adequate assurances, January could bring Oosterwolde back to the centre of Roma's transfer activity. The summer halt to negotiations need not mark the end of the story.

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.