Pennant's name was splashed all over the back pages when he moved from Notts County to Highbury in a £2million deal that left County alleging that the Londoners had poached their star talent.
Arsene Wenger moved to sign him after he had performed brilliantly in County's first team at the age of 15, and the manager is convinced that he will become a massive success.
The youngster's repertoire of tricks and huge self-belief make him great to watch: elegant on the ball and clever with his use of it, he has a rich rage of entertaining traits.
Had been capped by England at Under-15, -16, -20 and -21 level, and became Arsenal's youngest-ever first team player at the age of 16 on his debut in a November 1999 Worthington Cup tie against Middlesbrough.
In May 2001 made it to the England Under-21 set-up and thrived; all the while focused on following close friend Ashley Cole into both Arsenal's and England's senior teams.
You wouldn't bet against it happening sooner rather than later.
Only featured in Worthington Cup games in his early years with the Gunners, but he will surely remember coming on as a sub in Germany as Arsenal player Schalke 04 in the Champions League. Pennant replaced Nwankwo Kanu for the last 12 minutes of the game in October 2001.
Was rumoured to be available for loan with both Sheffield Wednesday and Preston North End strongly linked. Eventually joined First Division Watford for a month in January 2002, playing nine games and scoring two goals.
Had only made seven appearances for Arsenal by the start of the 2002/03 season, but was swiftly handed his Premiership debut in a 2-2 draw at West Ham United.
Rejoined Watford on loan in mid-November 2002.