Sunderland are exploring a major opportunity to sign a high-profile forward from AC Milan, as the Italian club face a crucial decision going into the January transfer window. Despite recently lifting morale with a derby victory, Milan remain troubled by uncertainty over their striking options — most notably the status of Santiago Gimenez, whose trajectory at the club has shifted dramatically from initial excitement to deep concern. Returning to Milanello, the squad began preparations for facing Lazio, but once again the conversation turned to Gimenez’s prolonged absence and declining condition.
This situation reflects a broader conflict: Milan urgently require reliable performances, yet they must also contend with a player hindered by recurring fitness issues and fading confidence. January could very well become the defining moment in determining how Milan reshape their attacking department.
Lingering Injury Troubles
Gimenez has been dealing with persistent swelling and pain in his right ankle for months, forcing him to step away from play and concentrate solely on recovery. In November 2025, he publicly acknowledged that he had been playing through serious discomfort for the sake of the team, until the pain reached a level he could no longer withstand.
He remains away from normal training routines, missing matches against Roma, Parma and Inter. His chances of appearing versus Lazio are slim, as he continues with a tailored rehabilitation plan. As more time passes, speculation over his future intensifies. Joining Milan in January 2025 brought big expectations, but sustained fitness and form never fully materialised.
A Career at the Crossroads
Sources such as Calciomercato point out that Gimenez’s difficulties extend beyond the physical realm. The psychological fatigue — frustration over missed goals and the burden of under-performance — has taken its toll. With Milan pushing for a Scudetto challenge, patience is thin: a dependable goalscorer is essential, and Gimenez hasn’t been able to deliver consistently.
Despite vocal support from Massimiliano Allegri, optimism has not translated into improvement. Milan must now determine whether waiting longer is sensible, or whether the moment has come to move on. For Gimenez, the ambition to break through remains, but the pressure is reaching breaking point — what insiders describe as “a point of no return.”
Sunderland and Brentford Enter the Contest
Now, his agent Rafaela Pimenta — who was instrumental in his Feyenoord departure — is again leading discussions. Her strong connections with Premier League clubs put England at the forefront of possible destinations.
Sunderland are stepping forward as a serious suitor, with Florent Ghisolfi having already investigated the possibility last summer. Their newfound ambition and stature make them an appealing option. Brentford are also closely tracking developments, while interest from elsewhere in Europe, including Turkish sides, continues to emerge.
However, Milan’s terms are firm: they want to recover the €30m investment made a year ago. His sale would directly shape their next move in the market, as finding a fresh No.9 becomes the top priority for executives Tare and Furlani.
Milan’s January Reconfiguration
This winter window may mark a tactical reset at Milan. Should Gimenez depart, their tactical structure and predicted lineup will naturally shift accordingly. Their title aspirations hinge on sharper attacking edge, and the full forward reassessment appears unavoidable.
EPL Index Perspective
For Sunderland fans, the prospect of landing Gimenez is both exhilarating and nerve-racking. The club’s identity has shifted dramatically under Ghisolfi, and the mere fact that Sunderland are even negotiating at this level — alongside AC Milan and other European forces — reflects how far they’ve progressed.
Gimenez offers a compelling profile: young, physically imposing, seasoned in European football, and previously a proven scorer before injury setbacks. Supporters have long argued the team needs a central striker capable of turning dominance into end product. In that regard, he feels like a perfect tactical fit.
But there is justified caution. Sunderland know all too well the dangers of costly gambles and rehabilitation-dependent transfers. There is emotional and psychological weight here as well — not just athletic rehabilitation.
However, the Premier League rewards bold recruitment — not timidity. If Sunderland intend to fast-track their evolution, these are precisely the types of opportunities they must be prepared to pursue. Even if the deal does not materialize, being seriously involved in this level of negotiation signals a revamped identity: ambitious, confident, and forward-driven.