Leon Bailey Joins Greek Giants Olympiacos After Five Years at Villa

Leon Bailey’s search for a new club has ended with a move to Greek giants Olympiacos, where he has secured a long-term contract reportedly making him one of the best-paid players in Greek football.

The Jamaican winger has signed until June 2029, with Aston Villa reportedly receiving around €4 million for the transfer. Earlier claims in Greek media placed the figure at €8.5 million, though that amount appears to have stemmed from a previously circulated valuation when Hull City were pursuing Bailey.

Olympiacos owner Vangelis Marinakis reportedly became directly involved in negotiations and helped push the transfer through rapidly. He had recently taken a similar hands-on approach to the club’s acquisition of Gustavo Puerta from Racing de Santander.

Bailey’s arrival adds to an extraordinary summer of spending for Olympiacos. The Greek club have now committed more than €65 million to transfers, the highest summer outlay in their history.

Despite the English transfer window closing on Tuesday, Bailey remained able to leave Villa because Greek clubs can continue completing transfers until September 15.

The move also resolves an issue Villa had been attempting to address throughout the summer. Manager Unai Emery had previously acknowledged that the club expected Bailey to depart, explaining before the Arsenal defeat that a transfer had already appeared close when the squad travelled to Asia for pre-season.

Villa’s deadline-day signing of Ibrahim Mbaye further reduced Bailey’s prospects. Mbaye was recruited for the same right-sided role, leaving little opportunity for the Jamaican to re-establish himself in Emery’s plans.

Several possible destinations had emerged before Olympiacos entered the picture. Hull City appeared particularly well placed to sign Bailey during August, with the Championship club working towards a permanent transfer.

That deal ultimately failed to materialise, with Bailey’s reported £120,000-a-week salary proving a major obstacle. Hull subsequently brought in Mohamed-Ali Cho from Nice.

Ajax and Sevilla were also linked with the winger, while Saudi clubs Al-Ittihad and Diriyah Club were mentioned as possible destinations. Bailey, however, appeared reluctant to pursue a move to Saudi Arabia, having also attracted interest from Neom SC in 2025.

There had even been discussion of Villa extending Bailey’s contract by another year to facilitate a loan, although a permanent departure was the club’s preferred outcome.

His exit closes a five-year spell at Villa Park that began when he arrived from Bayer Leverkusen in 2021. Bailey made 163 appearances for Villa in all competitions, registering 23 goals and 25 assists, and leaves with a Europa League winner’s medal from May.

His standout campaign came in 2023/24, when he played a significant role in Villa securing Champions League qualification. Bailey recorded 10 Premier League goals and nine assists that season, while adding another four goals during the club’s Conference League campaign.

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