Milan at Crossroads After Season of Domestic and International Setbacks | OneFootball

Despite being one of the most proactive Serie A teams in recent transfer windows, on-field success has eluded Milan this term. A season of frustration and upsets hit a new low last week.

First, Feyenoord crashed Sergio Conceicao’s side out of the Champions League knockout playoff round. Theo Hernandez’s brainless red card was Milan’s scourge at Europe’s top table, prompting the club to consider offloading him in the summer.

Second, Milan slumped to a dismal 2-1 loss at bottom-half Torino on Saturday. Another underwhelming league result forced an emergency meeting between the Rossoneri directors and Conceicao to address the team’s self-destructive performances.

With six points separating Milan from fourth-placed Lazio heading into Thursday’s away clash against Bologna, there’s no room for error. Adding to this sentiment, a quick peek into Betzillion’s list of best offshore sportsbooks shows Milan’s dire situation in Serie A.

Many leading bookmakers give the 19-time Italian champions slim chances of securing a fifth consecutive top-four finish. Failing to beat the odds would likely trigger a chain reaction that could culminate with several first-team stalwarts leaving the San Siro at the end of the season.

Left Side on Its Way Out

After Milan’s renewal talks with Hernandez hit a brick wall, the Frenchman’s summer exit has become a distinct possibility. The 27-year-old’s contract runs out in 2026, meaning Milan must sort out his future in the coming months.

Despite his woeful form in 2024/25, Hernandez remains among the world’s most highly-rated left-backs. In addition to long-term admirers Bayern Munich and Real Madrid, Manchester City have recently shown interest in the ex-Atletico Madrid star.

Milan will likely listen to offers for their long-serving ace. Furthermore, Rafael Leao could wave goodbye to Lombardy after five years. His inconsistent showings have failed to convince Conceicao, making the club contemplate his summer sale.

Like Hernandez, Leao boasts numerous high-profile suitors abroad, including La Liga powerhouse Barcelona. His departure would significantly boost Milan’s bank accounts and allow the club to finance incoming deals.

Other Potential Departures

Based on Conceicao’s early regime, there’s a feeling Samuel Chukwueze and Ruben Loftus-Cheek have no place in Milan’s new system. In the latter’s defense, he has been out with a long-term injury, though he was also on the fringes during Paulo Fonseca’s tenure.

As for Chukwueze, he has never found his feet in Serie A. Once a menace in Villarreal’s shirt, the Nigerian has flopped in Italy. Therefore, Milan could put him up for sale in the summer, irrespective of Riccardo Sottil’s future at the club.

Sottil joined Milan on loan from Fiorentina in January and has quickly leapfrogged Chukwueze in the pecking order. Though they operate on the opposite wings, Conceicao has often trusted him more than the 25-year-old.

Needless to say, Luka Jovic will depart the San Siro as a free agent.

Crucial Signing

Even without the lure of Champions League football, Milan should go all-out to sign Torino midfielder Samuele Ricci. Recently followed by Inter, Ricci is one of Italy’s finest talents and could be an ideal long-term replacement for Sandro Tonali.

Though Youssouf Fofana has enjoyed a decent maiden season in Serie A, Milan could use a leader in the engine room. Ricci ticks all the boxes. He’s Italian and only 23 years old, not to mention his vast experience in domestic football.