A few years ago, Cherki's family visited Milanello to negotiate with AC Milan. An intermediary was involved at that time, and the agreement appeared to be nearly finalized since Cherki was without a contract and essentially a free agent. Milan would have only been required to pay a training compensation. However, the deal ultimately collapsed due to a commission request of approximately 2 million euros from Cherki's entourage, which caused hesitance among Milan's management, led by Paolo Maldini.