In the summer of 2023, Bernardeschi was on the verge of leaving Toronto FC to join Besiktas. The Turkish club proposed a 3-year contract worth 4.5 million net per year, along with bonuses, and also offered an extra 1 million as a solidarity contribution to address tax issues. At the time, Bernardeschi held a 4-year contract with Toronto valued at 5 million per year, with an option to extend for 2 additional years contingent on appearances. The substantial financial disparity and tax complications ultimately led to the collapse of the transfer. Bernardeschi would have needed to relinquish a total of 1.5 million to resolve tax liabilities and an additional 6.5 million from his remaining contract with Toronto, rendering the move financially impractical and resulting in his continued stay in Major League Soccer.