Olympiacos officially announce the signing of Aston Villa's Jamaica international winger Leon Bailey..

Olympiacos announced on their official website on Thursday that they have signed Aston Villa's Jamaica international winger Leon Bailey.

According to the Greek Super League giants' official statement, Bailey has signed on a three-year deal with the club which runs until the summer of 2029. He will also wear the number 17 jersey.

About Leon Bailey

The 29-year-old Leon Bailey was born on August 9, 1997, in Kingston, Jamaica. He is 1.78 meters tall and primarily plays as a right winger, but can also play as a left winger.

Bailey played for his adoptive father's football academy in Jamaica during his childhood. In 2011, he went to Europe for trials with his adoptive brother Kyle Butler, and his outstanding performances attracted interest from Genk, Standard Liège, and Ajax.

However, due to Bailey's young age, which violated FIFA transfer regulations, he had to wait until he was 13 to be allowed to join the youth academy of RB Leipzig's satellite club, Liefering.

In 2013, Bailey moved to the Trenčín youth academy, but in 2015 he joined Genk, reuniting with Kyle.

In August of the same year, Bailey completed his Genk his first-team by coming on as a substitute.

During his two-year spell with Genk, Bailey won the Belgian Young Player of the Year award once and received the UEFA Europa League Goal of the Year award for his goal against Rapid Vienna in September 2016.

In January 2017, Bayer Leverkusen beat out numerous Premier League giants, including Manchester United, Chelsea, and Liverpool, to sign Bailey for €20 million.

During his five-year spell with Die Werkself, Bailey's outstanding performances often led to speculation that he could be naturalized as an England international, but all that came to an abrupt end in 2019 when he agreed to represent Jamaica.

In August 2021, Bailey joined Aston Villa for £30 million.

Since joining the Villans, Bailey has participated in the Champions League once, even breaking the tournament's record by becoming the first Jamaican player to score and assist in the competition.

In August 2025, Bailey joined Roma on-loan with an option to buy.

However, plagued by injuries, Bailey only made a few appearances for the Serie A giants in the first half of the season before being recalled early.

After his loan spell ended in January 2026, Bailey returned to the club, having recovered from his injury, and once again played for Villa's first team.

During his time at Villa, Bailey made 163 appearances for the Premier League club in all competitions, scored 23 goals and provided 25 assists. During which he won the UEFA Europa League once with the team and broke the record to become the first Jamaican player to score and assist in a Champions League match. 

Image source: Internet / Olympiacos official website