Jack Wilshere - massive media hype but never any end product to back it up - bear in mind he was in a relatively decent Arsenal side at the time.
Jamie Redknapp - All I ever remembered him for was injuries, and a goal against us when (muppet Enklemann?) was down fainted on the ground. Oh and that irrelevant free kick goal against Blackburn on the last day of the season and Blackburn still get to win the PL. He is a Ashley Westwood but may be a red Ferrari version
At present day, Virgil Van Dijk. He is good, but may be I am quite crtical in defenders, and growing up to see the likes of Maldini, Baresi, God etc. kind of make you feel VVD would have been just a decent central defender in comparison.