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He was once the youngest Gunner to ever play for Arsenal and he scored a hat-trick on his full Premier League debut. But Jermaine Pennant's promise didn't turn him into the star player many expected him to be for the Club.
Why he never really made it at Arsenal is open to debate. His pace and talent could make him thrilling to watch, yet he could not break into a team which at the time boasted the right-sided talent of Freddie Ljungberg.
Despite that, Pennant has made over 200 career appearances and most of those have been in the Premier League.
He joined Arsenal in 1999 from Notts County and that November he made his senior debut for Wenger's side. Aged 16 years and 319 days, his substitute appearance against Middlesbrough in the League Cup made him the youngest player ever to wear the Arsenal shirt until Cesc Fabregas came along.
After helping the Gunners claim back-to-back FA Youth Cup titles in 2000 and 2001, Pennant joined Watford on loan in January 2002.
Nine games later he returned to Arsenal and featured in the 4-1 win over Bayern Leverkusen in the Champions League, his second appearance in the competition. The following campaign he again went on loan to Watford, this time spending three months with the Hornets.
Then came what appeared to be his major breakthrough. Pennant started the Premier League game at home to Southampton in May 2003 - just days before the same teams would meet in the FA Cup Final. He tore the Saints to shreds, netting a first-half hat-trick to match Robert Pires' treble in the same match.
But despite taking home the match ball after that 6-1 win, Pennant never again scaled those heights with Arsenal.
In August 2003 he began a season-long loan with Leeds United, making 34 starts which included two against Arsenal.
The first half of the 2004/05 season saw him regularly feature in Wenger's Premier League team but in January of that term he moved on loan to Birmingham City, who signed him on a permanent deal that summer.
WHAT THE FANS SAID
We all have to have the same memory - a hat-trick on his Premier League debut against Southampton. He was totally amazing that day and seemed destined to be a firm fans' favourite. Unfortunately it didn't work out that way but at least he can have that great memory.
Emma Passmor, Yyne and Wyre
