3. Jack Wilshere (Arsenal – West Ham)
The only reason why he’s not at the top of this list is that he didn’t actually cost West Ham a transfer fee. The story of Wilshere is tragic and depressing. Technically speaking, he’s one of the most gifted footballers England has produced in the last twenty years. Sadly, because of his continuous injury woes, we’ve only ever seen it in patches.
Wilshere’s injuries followed him on a free transfer from Arsenal to West Ham where he has since lost hope of a starting place to Declan Rice, the young defensive midfielder who won plaudits from fans and pundits last season. The game looks like its passing Wilshere by. Don’t be surprised if he retires sooner rather than later.