4. Juan Cuadrado – Fiorentina to Chelsea (£26.1m)
Possibly the most pointless transfer of all-time. Impressive performances at the 2014 World Cup saw Cuadrado placed on the radar of Europe’s top clubs. His form continued into the 2014/15 season and, by the January transfer window, clubs such as Juventus and Arsenal were vying for his signature.
Jose Mourinho’s Chelsea won the race for the Colombian winger and he signed a four-and-a-half-year deal at Stamford Bridge. It went downhill from there though.
Making just 12 appearances in all competitions for the Blues between the transfer and the end of the season, Cuadrado’s future became uncertain. The aforementioned Juventus reignited their interest in the ex-Udinese man and signed him on a season-long loan for the 2015/16 season.
It remains to be seen what the future holds for the wide man.