Right Midfielder: Jermaine Pennant
http://www.youtube.com/watch?v=2-z8ftrdNYA Another player that will go down as having wasted potential, Jermaine Pennant was the
record fee for a trainee player when he signed for Arsenal in 1999. A pacy English winger with an excellent cross and an eye for goal, he should have been at the club to challenge Freddie Ljungberg and add another dimension to the club's attacking force. He became Arsenal's third-youngest ever player in the same year, but would have to wait until 2002 to make his Premier League debut. Despite scoring a hat-trick in his full league debut against Southampton, a match which coincidentally was the start of Arsenal's 49-match unbeaten run, he failed to secure a permanent spot in the team. His attitude was seen as the key problem behind why he wasn't getting regular game time. He would regularly turn up late for training, was very homesick at the beginning of his time at the club, and would complain often about his lack of first-team football. It was a difficult time for anybody to break into the team due to the consistency of their performances, and so he was sent out on loan numerous times, before eventually being sold to Birmingham City in 2005. Over time, his performances and attitudes have matured to a very high standard, but it is safe to say that his time at Arsenal came far too soon.
Other contenders: David Bentley, Luis Boa Morte