20David Bentley to Spurs
Given the weighty tag of the 'new Beckham' by Steve McClaren, a line which stuck, David Bentley appeared to be making true on those lofty comments during his three seasons at Blackburn Rovers between 2005 and 2008. Having struggled to break into the first team at Arsenal, Bentley became an
England international with Blackburn in his early 20s. He joined Tottenham in 2008, but despite a decent first season at White Hart Lane, Bentley's career soon began to fall apart. After a series of failed loan moves, Bentley retired age 29, having not had a club for over a year.