"Regret and shame": Arsene Wenger talks of the Arsenal transfer he wishes he could change

Speaking at a charity event this week, Arsene Wenger has revealed his "biggest regret" in the transfer market at Arsenal.

Wenger managed the club from 1996 until 2018, taking the Gunners from Highbury to the Emirates Stadium and winning 10 major trophies along the way, including the 2003/04 Premier League title in which his side went unbeaten.

As well as transforming the English game through sports science and dietary changes, Wenger brought in a number of the game's most prominent foreign imports, such as Thierry Henry and Cesc Fabregas. The Frenchman had a reputation for unearthing overseas gems, with Arsenal the first English side to field an entire XI with no homegrown players.

While Wenger's transfer policy became famous, his habits of talking about transfers months and years later became infamous, with the legendary manager spilling the beans on a whole raft of world-class stars that the north Londoners were in for. While speaking alongside former Arsenal co-owner and vice-chairman David Dein this week, however, there was one transfer that Wenger claimed he regretted above all others. 

"My biggest regret and shame is that Nicolas Anelka left," Wenger said. "He could have been special, instead he played for 13 clubs."

Clairefontaine graduate Anelka was bought by Wenger for just £500,000 in 1997 from Paris Saint-Germain. While at Arsenal, the young French starlet went became a fan favourite, scoring in the 1998 FA Cup final, as the Gunners completed the double.

Things turned sour during his time in England, however, with the striker claiming he "can't stand the English press" in May 1999. He was sold for £22m to Real Madrid, ultimately - with Wenger said to be heartbroken at the time at his protege wishing to leave so soon.

Arsenal and Wenger reinvested the fee that they received from Anelka in a state-of-the-art training ground. Wenger has always maintained that his next French striker, Thierry Henry, was never meant to replace Anelka, however, and that the plan was to play the pair together. 

Anelka went on to play for Liverpool, Manchester City, Bolton, Chelsea and West Brom in the Premier League.