Arsene Wenger was duped into making Arsenal's 'worst ever signing' after a training ground prank that went too far, according to former Gunners winger Jermaine Pennant. The north Londoners had a knack for recruiting top players during Wenger's time at the club, including the likes of Thierry Henry, Patrick Vieira and Dennis Bergkamp. However, not every deal turned out to be successful with some falling completely flat.

One of Arsenal's most notable transfer flops was the signing of Latvian defender Igors Stepanovs. He joined in 2000 but only made 31 appearances for the club before leaving in the summer of 2004. Pennant, who played alongside Stepanovs, described him as the worst signing Arsenal had ever made and told an interesting story about how the move came about.

"I would say the worst signing ever for Arsenal was Igors Stepanovs," Pennant told The Mirror. "I have no idea what Arsenal was thinking, but I know the story behind it. It was Dennis Bergkamp and Ray Parlour, trying to wind up Martin Keown, saying: 'Oh, wow'.

"He played a training match, but Bergkamp and Ray Parlour were going: 'Oh, he’s unbelievable'. In front of the boss, in front of Martin Keown.

"Then a week later, he comes walking in on a four-year deal. Four years and it was so bad. It was bad. Probably one of the worst signings I’ve seen."

Stepanovs joined Arsenal following an injury to Tony Adams and made the perfect start by scoring on his debut against Ipswich Town. However, things went downhill from there and he never managed to prove himself as a dependable asset.

He started in a crucial game against Manchester United, which resulted in a 6-1 defeat with Dwight Yorke bagging a hat-trick in the first half. It marked a turning point for Stepanovs, who played just once more that season before joining Swiss club Grasshoppers.

Reflecting on the infamous match at Old Trafford back in 2021, he told The Athletic: "It wasn’t a good game. I went back and watched the highlights and analysed myself. In some ways I was unlucky.

"Sometimes you’re close to the striker, you’re not doing much wrong, but the ball jumps over your foot and goes in. It felt like they just scored every chance they had. It was bad, but that’s football.

"People like to judge and that’s up to them. Maybe the reaction was so strong because it wasn’t just a game against any team, it was Manchester United.

"The manager and I talked after the game. I understood where he was coming from. He was under pressure. We’re not kids. You’re at Arsenal, you know the expectations.

"You know you’ve made a mistake. You’ve lost your chance. But for me, it was important to not stop, to continue to train and to get back. You must not give up. You need to stop talking and train harder."