Philippe Coutinho — Liverpool to Barcelona (2018) — €160 million

Philippe Coutinho's £142 million (€160 million) move from Liverpool to Barcelona in January 2018 was at the time the third most expensive transfer ever. Barcelona used money freed from Neymar's sale to fund the deal. Coutinho never fulfilled his potential at Camp Nou, returning to English football via a loan to Bayern Munich (where he won the Bundesliga) before ultimately joining Aston Villa at a fraction of his fee. His career trajectory became a cautionary tale about how transfer fees can destroy player confidence and distort expectations.