Italian forward Federico Chiesa’s time at Liverpool could be approaching its conclusion, with reports in Italy suggesting that AC Milan are plotting a surprise reunion between the winger and Massimiliano Allegri. According to SempreMilan, Milan are considering a €5 million move for Chiesa, who has struggled to cement a regular place in Liverpool’s starting lineup since his high-profile switch from Juventus.

 

Chiesa, 27, arrived at Anfield with high expectations following a stellar Euro 2020 campaign and several impressive seasons in Serie A. His pace, directness, and ability to produce match-winning moments made him one of the most sought-after forwards in Europe. However, his time in England has been mixed. While flashes of brilliance have reminded Liverpool fans of his talent, persistent injury setbacks and tactical rotations under manager Arne Slot have limited his impact.

 

This lack of consistent game time has sparked speculation about his future. With Liverpool boasting an attacking lineup featuring Mohamed Salah, Luis Díaz, Darwin Núñez, and Cody Gakpo, Chiesa has often been used as a rotational option rather than an automatic starter. The situation has reportedly caught the attention of Milan, who are eager to strengthen their wide options and inject more experience into their squad.

 

The Rossoneri’s interest is said to be driven by Allegri, who returned to Milan this summer after departing Juventus for the second time. Allegri knows Chiesa well from their shared time in Turin and is believed to be confident that he can help the forward rediscover his best form. A €5 million deal would represent a bargain price for a player of Chiesa’s pedigree, though Liverpool would likely want assurances regarding add-ons or a sell-on clause before sanctioning the move.

 

From a tactical perspective, Chiesa could fit seamlessly into Milan’s 4-2-3-1 system, offering width and creativity from the right flank. His ability to cut inside, press aggressively, and contribute defensively would make him an ideal addition to Allegri’s plans. For Chiesa, the move would represent a chance to return to Italy, where he might enjoy more consistent minutes and re-establish himself as a key figure for the Azzurri ahead of Euro 2028 qualifiers.

 

Liverpool’s decision will depend largely on their long-term vision for Chiesa and whether they view him as an important squad player or as someone they are prepared to move on from. With the club in transition following the departure of Jürgen Klopp earlier this year, there is still uncertainty about which players will form the core of Arne Slot’s project.

 

For now, the speculation surrounding Chiesa adds an intriguing subplot to Liverpool’s season. If Milan succeed in their pursuit, it could mark one of the most interesting transfers of the January window – a move that might give Chiesa the platform he needs to reignite his career and once again become one of Europe’s most exciting wide players.