Liverpool may be on the brink of a historic title-winning season, but a summer of sweeping change appears inevitable. One player who could be headed for the exit is now at the centre of a bold project – only it’s not on Merseyside. According to Anfield Watch, “According to the latest reports, Federico Chiesa is highly regarded, although his admirers are over at AC Milan rather than Liverpool. The San Siro based club are looking to hire a new manager and a new sporting director this summer and they have ambitious plans.”
Milan’s intent is clear: a return to domestic roots, a reset built around Italian talent, and a tactical evolution with new leadership at the helm. The forward in question, brought to Liverpool just six months ago, is now being targeted as a key figure in this strategy. Gazzetta reports that he’s high on Milan’s list as the Rossoneri aim to blend identity with competitiveness.
The forward’s arrival at Anfield was one of pragmatism rather than long-term planning. With limited availability in the final days of the summer window, Liverpool saw an opportunity to bring in a proven international with pedigree at a reduced price. His situation at Juventus had deteriorated, and the Reds seized the chance.
Despite his obvious talent, the move has yet to bear fruit. Injury setbacks have limited his impact, and when available, game-time has been sporadic. As Anfield Watch notes, “Now six months into his stay, it is clear that the move hasn’t quite worked out.” Still, he’s managed two goals and one assist in just under 400 minutes — a hint at what might be if rhythm and trust could be restored.
Arne Slot, still in the early months of his Liverpool tenure, has shown reluctance to rely heavily on him. This hesitation, combined with the player’s own ambitions — especially with the 2026 World Cup looming — has led to speculation over an early departure.
The player’s contract runs until 2028, but time is rarely on a footballer’s side, especially when national team places are on the line. A return to Serie A, particularly in a starring role for a club with Milan’s stature, would certainly appeal. Game-time, tactical fit, and visibility to the Italian national team manager would all improve — factors not lost on the player or his representatives.
From Liverpool’s point of view, the situation poses a dilemma. Cut their losses now, or give the move more time to flourish? As Anfield Watch highlights, “Liverpool only brought the Italian to Merseyside this summer… but the Reds’ senior officials might already want to cut their losses.”
In a squad already under scrutiny — with attacking roles uncertain for Luis Diaz, Diogo Jota and Darwin Núñez — this case reflects the broader questions Liverpool must answer ahead of 2024/25.
Milan’s reported intention to prioritise Italian players as part of their rebuild brings urgency to their approach. They’re not simply looking to reinforce — they’re reshaping an identity, and want ready-made stars to lead the project. The forward in question fits that brief and would be a significant statement in the Italian market.
For Liverpool, whose current forward line is still unbalanced, there’s a temptation to cash in — particularly if it aids further structural investment in defence or midfield. The decision, however, will need to be weighed carefully. Offloading a player with such quality, after such a short time, could either be prudent or premature.
For Liverpool, this one feels like a misfire — but not an unsalvageable one. Chiesa clearly has ability, and when fit, offers traits no one else in the squad truly replicates: direct running, intelligent movement, and a flair for the unpredictable. The problem? We’ve barely seen it. And with Arne Slot still finding his feet, there’s little time for passengers.
That said, letting him go now would sting. Six months is hardly a fair assessment window, and injuries have played a major role. With Diaz possibly heading out and Jota’s fitness concerns lingering, having depth — especially of this calibre — is essential.
If Milan do come knocking, fans would want to see Liverpool drive a hard bargain. Selling cheaply would feel like a mistake, especially with the player’s reputation still high on the continent. But if the deal brings in significant funds and frees up space for someone who suits Slot’s vision more precisely, there might be logic in making the move.
Still, most Reds would prefer the player gets a full pre-season and a real chance. Talent like his doesn’t come cheap — or often.
