BAILEY’S GREEK ODYSSEY

With Reggae Boyz winger Leon Bailey moving to multiple-time Greek champions Olympiacos FC, Greece-based sports writer Nikos Kotsis says his pedigree makes him a needed addition to the squad. Bailey, who successfully completed his medical, was presented by Olympiacos on Wednesday. He moves to Super League Greece on a permanent deal, signing a three-year contract which ends a five-year stint with reigning Europa League champions Aston Villa. “I’m very happy to wear the red and white shirt and I can’t wait to experience the atmosphere at the Karaiskakis Stadium,” he said in a video on the club’s social media. Olympiacos have won the Greek top flight 48 times in their history, although they finished runners-up to AEK Athens last season. The club, who will compete in the UEFA Europa League season, made the knockout phase play-offs of the UEFA Champions League last season and won the UEFA Conference League title in 2024.

Reggae Boyz winger Leon Bailey smiling with the Olympiakos FC scarf after joining the 48-time Greek champions from English Premier League club Aston Villa on Wednesday, September 2, 2026.

Olympiacos have been busy this transfer window, signing close to 20 players. Kotsis, who writes for several Greek outlets, including Sports 24, says Bailey’s arrival is among the top and believes he can make a real impact. “Bailey’s arrival in Greece is a move that improves the attacking midfield of Piraeus,” Kotsis said. “If the Jamaican is healthy and has no problems, he will be a player who can make a difference. A winger with rich performances at the top level and a career full of brilliance. “At 29 years old, the absolute leader of the Jamaican national team, Bailey is in the most mature phase of his career. Olympiacos adds to its roster a pure-blooded killer of the wings, capable of breaking down any defense in one-on-one. And now we are counting down to his arrival in Athens.” Greek Sports Journalist Kostas Lianos reported that the deal is worth £2million ($427 million) and Bailey is set to earn £1.6 million ($342 million) per year until 2029.

Jamaica’s Leon Bailey (left) and New Caledonia’s Jekob Jeno fight for the ball during the 2026 FIFA World Cup qualifiers semi-final play-off match at Akron Stadium in Zapopan, Mexico, on March 26, 2026. (Photo: AFP)

Bailey was thought to be staying in the English Premier League with newly promoted Hull City on the verge of securing his signature. However, the move ultimately broke down with manager Sergej Jakirovic calling it “a mess” while Bailey’s representative Craig Butler told the Jamaica Observer that they were weighing up their options with several clubs interested. Bailey failed to secure a move before the close of the English transfer deadline on Tuesday, with reports saying that he could be off to Saudi Arabia with Al Diriyah and Al Ittihad among the clubs interested given their transfer window closes on Saturday. Although he had another year left on his contract with Aston Villa, Bailey was told by manager Unai Emery that he wouldn’t be part of his plans for the season, despite being an active part of their preseason. Bailey joined Serie A club AS Roma on loan last summer but cut his loan deal short after limited game time and injuries and rejoined Villa in January where he went on to make 19 appearances. He won the Europa League title and saw Villa finish fourth in the league to secure a spot in this season’s Champions League. Bailey, who joined from German club Bayer Leverkusen for £30 million in 2021, made 163 appearances and scored 23 times in all competitions. His best season came in the 2023-24 campaign where he registered 10 goals and 10 assists in the Premier League, one of the few players to hit double digits in both categories. Bailey’s departure means only four Jamaican internationals will be in the Premier League this season. They are Coventry City’s trio of Ethan Pinnock, Joel Latibeaudiere and Ephron Mason-Clark, and Brentford left back Rico Henry.