Leon Bailey (born 9 August 1997, age 29) is a Jamaica international right winger now with Olympiacos. His early senior career was shaped by spells away from a settled first-team base, with loan football giving him the sort of adult minutes that tend to strip the polish off a young winger quickly enough.
He built his wider reputation in European football before moving on to Aston Villa, where his best league return came in 2023-24: 10 goals in 35 appearances. That was the season in which his pace and direct running came with enough end product to matter regularly, rather than just threaten to.
At Olympiacos in 2026-27, Bailey has made two appearances across all competitions, one in the Super League and one in the Europa League. His market value is around ยฃ18.5m, according to Transfermarkt.
He has also remained involved with Jamaica this season, playing in two World Cup qualifiers and three Gold Cup matches, scoring once in the Gold Cup. His career to this point has taken him from early developmental spells into established top-flight football, with his strongest club campaign still the 2023-24 season at Aston Villa.
📈 Key stats and insights
