Pennant was signed at the age of 15 by Wenger in 1999 for £2 million (a record fee for a trainee at the time) from Notts County. He endured long spells on the bench at Highbury and unfortunately the Englishman never lived up to his potential. Instead, the winger suffered from major disciplinary problems which affected him from settling into the club. Pennant had a couple of loan spells at Watford and Leeds United before he was let go by Arsenal and was sent packing to Birmingham City in 2004.
Possibly the worst signing Wenger has ever made in his managerial career. Why Stepanovs was bought to the club is beyond me and possibly most of the Arsenal fans reading this. The 6’ 4’’ centre-back was absolute garbage and the 6-1 battering at the hands of Manchester United at Old Trafford proved this testament. Wenger paid £1 million to Skonto Riga (a Latvian club) in 2000 for Igor Stepanovs services. The defender made 17 appearances before moving to K.S.K. Beveren in 2003. Stepanovs was a complete and utter joke for Arsenal, and that’s me being nice!
Jeffers was playing his club football for Everton and impressed so much that Wenger opted to sign him from the Toffees in 2001 for a surprising £8 million. Everton must have been laughing all the way to the bank when they sold the striker for as much as they did. Jeffers spent 3 years with Arsenal, making a total of 22 appearances and managing to only score a measly 4 goals for the North London club. The English striker was ultimately sold to Charlton for £2.6 million in 2004, as he was forced out by better forwards in Thierry Henry and Sylvain Wiltord. A fox in the box? More like a frog in the bog.
Richard Wright Joined Arsenal in 2001 from Ipswich Town for an estimated £6 million, after a countless number of splendid performances for the Tractor Boys impressed the French manager. Wenger brought in the English goalkeeper as a successor to David Seaman, but failed to make an impact for the Gunners. His calamity against Charlton Athletic which led to a home 4-2 defeat for saw the fans question the goalkeeper’s ability. Wright also suffered a long-term injury which saw the keeper drop to third choice behind Stuart Taylor. Wright’s only year at Arsenal was below average, but the goal-stopper was also plagued with a number of injuries and only managed to make a total of 22 appearances for the club…he was later sold to Everton.