Dean Ashton is a difficult player to include on this list. He was a stand out player in his Norwich days and in no way were his performances for West Ham a mockery to his £7 million price tag. However, he was tormented by an injury that forced him to retire at the ridiculously young age of 26, playing just 46 games in the three seasons he was with Hammers. This included almost two full successive seasons out. Despite his obvious talent and the unfortunate nature of his recurring injury, that still amasses to almost two entire seasons that West Ham paid his impressive wages with nothing to show for it. His position as star striker hasn't really been filled since - Andy Carroll being the only notable potential successor (that's if he can quell his injury problems too), and this has only added to the significance of Dean Ashton's retirement. His ability was never questioned, but due to the events that unravelled throughout the course of his West Ham career, Dean Ashton finds himself very much on this list.
