Jermaine Pennant
Pennant moved from Notts County to Arsenal when he was still only 15-years-old in 1999, for what at the time was a record fee for a trainee. He only ever made 12 appearances for the Gunners in the top flight, and didn’t really find his feet until a permanent transfer to Birmingham in 2005 was completed after numerous loan spells. Here he excelled, earning a transfer to Liverpool, where he competed in their failed Champions League final in 2007. Pennant’s now a bench player at Stoke.