Voetbalnieuws.be reports that Club Brugge is interested in Leon Bailey as a potential winter transfer target. The club is considering the player, who is under contract at Aston Villa and on loan at AS Roma, for an attacking reinforcement. Club Brugge views Bailey as a player profile that is both intriguing and risky, with a notable past and a fluctuating present. The financial aspect of the deal is complex; Bailey originally joined Aston Villa for a fee of more than 30 million euros, but his market value has now decreased to around 20 million euros due to his age, contract length, and injury history. This amount is generally beyond Club Brugge's financial capacity, unless alternative arrangements such as a loan with an option to buy, a shared salary burden, or a structure where Aston Villa retains some risk are used. Bailey's salary is above Club Brugge's typical range, but it is suggested that players in his situation may sometimes make concessions to become important again.

Leon Bailey, who is on loan at AS Roma from Aston Villa, is expected to leave the Italian club due to a lack of playing time, but Aston Villa does not have a position for him in their squad, necessitating a move to a new club. The Spanish lower-table team Girona is reportedly a candidate to take over his loan. It is also suggested that Belgian top clubs such as Club Brugge and Anderlecht might be interested, as both are looking to add players to their wing positions and are seeking a left-footed player who can play on the right, a profile that matches the Jamaican international. However, a return to the Jupiler Pro League for the 28-year-old is considered unlikely and would only be feasible as a loan, with any Belgian top club only having to partially cover his significant Premier League salary. The winger has made 7 appearances for Roma in Serie A this season without providing a goal or an assist. For his country, Bailey has 39 caps and 7 goals. His loan to Roma in August 2025 included a reported fee of €2-3 million with an option to buy between €20 million and €25 million. His last permanent transfer was from Bayer Leverkusen to Aston Villa in August 2021 for a reported €32 million. His current market value is estimated by Transfermarkt to be €18 million.