George Weah disclosed that his son, Timothy Weah, was on the verge of joining Milan during the period when Paolo Maldini was associated with the club. George had engaged in discussions regarding Timothy with Maldini; however, the transfer did not come to fruition. Upon Timothy's mention of an opportunity with Juventus, George advised him to seize it without delay. The family and his manager concurred that it was a rare opportunity, and they believed Juventus was the appropriate team for him.

Timothy Weah could have played for Milan. His father, George Weah, contacted Paolo Maldini, but the transfer did not proceed. It seems there was no budget available for the transfer or perhaps not for Maldini, who was dismissed shortly thereafter. In those months, Juventus secured Weah for 10 million euros, as the only acquisition during the austere summer of 2023.

Vlahovic is unavailable for Milan, so Juventus will have Timothy Weah play as a striker in the stadium that celebrated his father, Big George.