10 Most Expensive Transfer Flops In Premier League History

9. Jose Antonio Reyes

In the early 2000s, Reyes was undoubtedly one of the brightest young players in Spanish football. He was a flying winger with vast potential at Sevilla, and when Arsene Wenger snapped him up and took him to Arsenal in January 2004, many felt he would flourish alongside the soon-to-be 'Invincibles' Thierry Henry, Dennis Bergkamp, Patrick Vieira and Robert Pires. It didn't go to plan though. Despite an impressive start to life in north London, including two goals against Chelsea in the FA Cup, Reyes struggled with the physical side of the Premier League and found it hard to dislodge the likes of Pires and Freddie Ljungberg in Wenger's first-choice starting eleven. There was the odd flash of class here and there, but his performances lacked influence and consistency throughout. He was sent-off in the 2005 FA Cup Final- Arsenal still beat Manchester United though, on penalties- becoming only the second player at the time to do so, and around that time he also complained of homesickness. Despite signing a new long-term deal at the club that summer, he left to join Real Madrid a year later. It brought an end to a very forgettable two-and-a-half years in England.