Olympiacos is considering acquiring Leon Bailey to reinforce its attack on the wings, a reinforcement manager José Luis Mendilibar views as necessary. According to reports, the 29-year-old Jamaican winger is a new name being considered, and he is said to be high on a list of targets that also includes Tiago Nus. It is believed that the club will certainly acquire one of the two players, and a scenario exists in which both could be signed if Gelson Martins departs. Bailey has 41 caps and 7 goals for Jamaica and is contracted with Aston Villa until the summer of 2027. In the preceding season, which he divided between Aston Villa and Roma, Bailey made 30 appearances, recording one goal and one assist in approximately 900 minutes of play. His current market value on Transfermarkt is €14.00m. Al Ittihad, Sevilla, and Ajax are other clubs that have recently been linked with him. Reports from August 2026 indicate that Aston Villa's asking price is between €9 million and €10 million. This is lower than his transfer fee from August 2021, which was reported to be €32 million.