5) David Bentley
Although never a truly excellent player, David Bentley’s quick decline was still pretty staggering. After showing some promise as a youngster at Arsenal, Bentley truly found his feet at Blackburn Rovers before earning regular call-ups for England and then a big-money move to Tottenham Hotspur. After a bright start, it all fell apart for Bentley and he spent years struggling to find a club before retiring at the age of just 30.