Leon Bailey Moves to Olympiacos
Leon Bailey’s five years at Villa Park are over, after a move to Olympiacos, was wrapped in seemingly quick-time. While English football’s transfer window may have slammed shut on Tuesday, the Greek Super League’s transfer deadline doesn’t close until 15 September, which is why the deal could still be done yesterday.
The move is a genuine surprise: Olympiacos hadn’t previously featured among the clubs linked with Bailey this summer.
The Marinakis Factor
Olympiacos owner Vangelis Marinakis is reported to have taken personal charge of the negotiations and closed the deal quickly, having already done the same when signing Gustavo Puerta from Racing de Santander. Olympiacos have now spent more than €65m on transfers this summer, an unprecedented figure in the club’s history. Bailey’s contract, according to Greek media, makes him one of the highest-paid players in Greek football.
The 29-year-old has signed a contract running until June 2029, with the transfer fee reported to be around €4m. Greek reporters had originally suggested the fee was €8.5m, but that looks like guesswork based on a fee floated on social media when Hull City were in for the player.
Villa have been trying to move Bailey on all summer. Unai Emery said as much ahead of the recent Arsenal defeat, admitting Villa had expected to sell him while they were on their pre-season Asia tour.
“We were expecting him to leave,” Emery said. “When we left for Asia, he was close to leaving.”
The signing of Ibrahim Mbaye for the same right-sided role, announced on deadline day, only sharpened that need. There was no longer a route back into Emery’s side, so Bailey needed a solution.
Bailey’s Summer of Links
Hull City had looked the likeliest exit for most of August, with Villa working towards a permanent deal and Hull’s president saying it should be finalised within days. A move never materialised. Bailey’s reported £120,000-a-week wages proved the sticking point, and Hull later signed Mohamed-Ali Cho from Nice instead.
Links to Ajax and Sevilla surfaced, but again, unlikely to be completed, as his wages were always going to be a stumbling block. There was talk of extending his contract by a year to enable a loan, but Villa would clearly prefer a clean break. The best bet for that was thought to be Saudi sides Al-Ittihad and Diriyah Club, but Bailey seemed to have dismissed a move to Saudi, as he did when Neom SC showed interest in him in 2025. His recent injuries and decline in form perhaps limited the scope of his wages even in Saudi, so Olympiacos, it seems, ended up being Bailey’s preference for the all-round offering.
His Champions League Qualifying Season
Bailey joined Villa from Bayer Leverkusen in 2021 and leaves having made 163 appearances for the club, scoring 23 goals and adding 25 assists, with a Europa League winner’s medal from May among the honours. His 2023/24 season was clearly his best at the club, helping Villa qualify for the Champions League, with 10 league goals and nine assists, and a further four goals in the Conference League.
Bailey’s Decline
A sharp decline was to follow though. Towards the end of 2024, during the 2024/25 season, MOMS learned that the club’s football department had been genuinely surprised by the drop-off of the side’s attacking players. Nobody was singled out, but there was little doubt Bailey was top of the list. The winger took until January to score what would be his only league goal of the season. A failed loan at Roma, which initially stalled due to him getting injured as soon as he joined the Italians, typified his fortunes since.
At 29, with a year left on his contract and no route back into Emery’s plans, moving Bailey on was always about limiting the financial drain rather than getting value. Getting his wages off the books and collecting what is essentially akin to the loan fee Roma paid last season is probably as good as the club could have hoped for.
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