GdS: Donnarumma, Calhanoglu, Kessie – Maignan could join list of painful free transfers

Mike Maignan could become the latest player to leave AC Milan on a free transfer, and there have been some painful cases.

As La Gazzetta dello Sport (seen below) write this morning, Maignan is more likely to depart Milan before the start of next season than he is to renew. Chelsea and Bayern Munich are apparently interested, but Juventus have come forward too.

Going to a direct rival is a painful possibility for the fans to consider. Recent free transfers like Davide Calabria, Alessandro Florenzi and Olivier Giroud have been far less controversial, given their respective times had come to try something new.

The ones that sting

Let’s go back to 2021, for example. Milan had just secured Champions League qualification on the pitch after a seven-year absence, but the newspapers were preoccupied with the issues surrounding Donnarumma and Calhanoglu.

Both were key starters, and their contracts are expiring. Discussions over Gigio’s contract renewal had been ongoing for some time, until the Rossoneri surprisingly made the signing of Maignan.

The Frenchman unexpectedly showed up in Milan for a medical, on May 27 his signing was already official, completely surprising Donnarumma. Negotiations for a new contract broke down, with Gigio first winning the European Championship as the tournament’s MVP and then signing for PSG.

Even more surprising was Calhanoglu’s departure on a free transfer, for whom Milan had submitted an offer and were expecting a yes. The Turk, however, declined and accepted Inter’s offer, which came after Eriksen’s heart problem. He went from one side of the Navigli to the other as if it were nothing.

In 2022, however, it was the turn of Romagnoli – who in the meantime had lost his starting spot – and especially Kessie. The Ivorian was presented an offer from Barcelona and departed, leaving a void in midfield that Milan would struggle to fill. Three years later, it could be Maignan’s turn.