Milan risk missing out on Bennacer, Theo Hernandez and Chukwueze cash

Milan is experiencing a challenging transfer window, as Olympique Marseille is unwilling to trigger the €12m buy option for Ismael Bennacer, while Atletico Madrid's €15m offer for Theo Hernandez is significantly lower than expected. This situation could lead punters to consider betting against Milan's ability to strengthen their squad effectively during this transfer period, potentially influencing their performance in the upcoming season.

Milan are facing problems, as Olympique Marseille won’t pay the Ismael Bennacer option, while Atletico Madrid offers for Theo Hernandez and Betis for Samuel Chukwueze are too low.

The Rossoneri have failed to qualify for any European competition this season after finishing eighth in the Serie A table, which means they will have to tighten their belts a little.

Though Tijjani Reijnders is on his way to Manchester City, they were still hoping to bring in some fresh revenue with other player sales.

Milan had hoped to cash in on players.

MILAN, ITALY – APRIL 02: Theo Hernandez reacts during the Coppa Italia Semi Final match between AC Milan and FC Internazionale at Stadio Giuseppe Meazza on April 02, 2025 in Italy. (Photo by Marco Luzzani/Getty Images)

The first was Bennacer, who had an option to buy for €12m which Olympique Marseille are not prepared to pay.

Because the midfielder made only 12 appearances in his six-month loan, Calciomercato.com argue Marseille are hoping to negotiate another loan experience instead.

On top of that, Sky Sport Italia transfer pundit Gianluca Di Marzio warns that the opening Atletico Madrid offer for Theo Hernandez is only €15m, considerably lower than they were hoping for.

It’s a blow after the player rejected a far more lucrative proposal from Al-Hilal.

MILAN, ITALY – OCTOBER 19: Samuel Chukwueze scores the opening goal during the Serie A match between AC Milan and Udinese Calcio at Stadio Giuseppe Meazza on October 19, 2024 in Italy. (Photo by Marco Luzzani/Getty Images)

Chukwueze is also on his way out, but negotiations with Real Betis are still at very early stages.

It is unlikely to match the €21.1m plus up to €7m in add-ons that the Rossoneri paid to sign him from Villarreal in 2023.

Milan are facing problems, as Olympique Marseille won’t pay the Ismael Bennacer option, while Atletico...

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