20. Arjen Robben: 2004-07
Before he became a star at Bayern Munich, Arjen Robben made his name at Chelsea FC under Jose Mourinho. While he does not seem like a traditional Mourinho player because of his lack of defensive work, Robben was precisely the sort of pacey winger that a manager craves.
Equally adept at playing on either wing, Robben joined Chelsea for £12.1 million from PSV Eindhoven but injuries in preseason prevented him from making an instant impact. That was essentially the story of Robben’s career at Chelsea but he was still able to make a difference when healthy.
In 2005 and 2006 he was an integral part of the Blues’ title-winning sides and managed to make 40 and 37 appearances in all competitions in his final two seasons with the club. In his time at Stamford Bridge, Robben won two Premier League titles, an FA Cup, and two League Cups.
Real Madrid came sniffing around for the winger in 2007 and made an offer that the Blues could not refuse as they bid £24 million for his services. Things did not quite work out at Madrid but he has since become a global superstar at Bayern Munich. One can only think of what Robben could have accomplished had he spent the majority of his career in West London but given the trophies he has won at both clubs it is highly unlikely that the Dutchman has any regrets about the move.
Next: #19