Ajax will look to sign 29-year-old Jamaican international Leon Bailey from Aston Villa in the final weeks of the summer transfer window.
According to a report by Sky Sports journalists Anthony Joseph and Tim Thornton, Leon Bailey is the subject of interest from Ajax. The Eredivisie heavyweights are eager to bolster their offensive unit by signing a wide attacker in the coming days, and they have set their sights on the 29-year-old Aston Villa winger.
Per Anthony Joseph and Tim Thornton, Ajax and Aston Villa have held initial talks to discuss a possible move for the former Bayer Leverkusen winger. The report adds that the Dutch giants are “exploring the conditions of a deal” and considering making an “official offer” to sign Bailey in the final weeks of the ongoing transfer window.
Leon Bailey and his Aston Villa journey so far
Leon Bailey has been at a crossroads in his career since struggling for regular starts in the 2024/25 season. The Kingston native would have hoped to resurrect his fortunes after joining AS Roma on loan last summer, but managed only 318 minutes of game time in 11 appearances for the Serie A outfit, chipping in with two assists.
The 29-year-old returned to Aston Villa midway through the 2025/26 season, and he enjoyed a slightly more prominent role, making 19 appearances while chipping in with a goal and an assist. However, the Villans, who paid £25 million to sign the player, are ready to part ways with him in the ongoing transfer window, and an adventure in the Netherlands may be on the cards.
Eredivisie adventure beckoning?
Ajax’s interest in Leon Bailey is understandable. The Eredivisie giants have been scouring the market for a wide attacker, as Michel’s squad is short of options for the right flanks. While Steven Berghuis is the first-choice starter on the wing, he is on the wrong side of 30 and approaching the twilight of his career.
So, Ajax must invest in a new wide attacker, with Bailey emerging as a viable target. The situation also explains the Dutch club’s readiness to submit an offer to Aston Villa, and they will hope to take advantage of Hull City’s decision to call off a move.
The Tigers were once close to signing the Jamaican winger, but talks over a summer deal recently collapsed. With Ajax having a clear run at Bailey, a summer move to the Eredivisie may be on the cards for the out-of-favour Aston Villa forward.
