Jermaine Pennant (App: 12; Goals: 3; 1999-2005):
One of many English youngsters who fell prey to the over-hype and expectations laid on him by top English clubs, Jermaine Pennant was a picked up by Wenger at just 15-years of age. He had a number of issues on an off the field and was just not able to adjust to the challenges in an Arsenal shirt that early in his career.