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Serge Aurier
Obviously these are all hypotheticals, but I'm not convinced that a David Bentley does necessarily have more contacts at top clubs compared to a Dean Windass. I know a couple of guys (not ex pros) who work in non league football who have plenty of contacts in the Premier League at both scouting and exec levels.
My assumption is actually that the majority of agents aren't ex players actually ex players at all, so that 'circle' of people with the contacts and general knowledge of the way the system works isn't as much of a closed shop as it used to be. Which goes back to my point about professionalism opening the industry up.
It's fairly interesting to look at the FAs list of registered intermediaries for recognisable names (...neither Bentley or Windass are on it at the moment )
Who are you, Jimmy two times - im gonna go get the papers get the papers!