Jermaine Pennant
Jermaine Pennant signed for Arsenal in 1998 from Notts County for £2 million when he was just 15-years-old, which was a huge amount in those days for such a young player.
He became Arsenal’s youngest ever youth team player (a record later broken by both Cesc Fabregas and Jack Wilshere) when he played in the League Cup on 30 November 1999 and looked to be a promising winger that could learn from and eventually replace Robert Pires and Freddie Ljungerbg.
It wasn’t to be. With the strength of the Gunners forward line his chances in the first team were limited to just five starts in his seven years at the club. He was also plagued by bad attitude problems, indiscipline and off the pitch behaviour which resulted in him shipped out.