Arsene Wenger has admitted that one player’s departure from Arsenal was his “biggest regret” ahead of Thierry Henry, Robin van Persie and Cesc Fabregas.
The 72-year-old Frenchman sold a whopping 389 players during his remarkable 22-year career at Arsenal, according to Transfermarkt.
Wenger, who stepped down as Arsenal manager in 2018, oversaw the departure of prolific Arsenal players and controversial transfers.
Arsenal legend Henry left the north London club in 2007 to complete a £16.1m transfer to Barcelona in 2007.
Van Persie exited Arsenal in 2012 to make a controversial transfer to Manchester United in an initial deal worth around £22.5m.
Another high-profile transfer Wenger sanctioned was the sale of former Arsenal captain Fabregas, who signed for Barcelona in 2011 in a deal worth around £35m.
However, Wenger has now claimed it was a “shame” to see Nicolas Anelka leave Arsenal.
Speaking at an event alongside former Arsenal co-owner and vice-chairman David Dein, he said: “Yes, we used the Arsene Wenger card and players wanted to go to where they would win.
“My biggest regret and shame is that Anelka left. He could have been special, instead he played for 13 clubs.”
A young Anelka arrived at Arsenal in 1997 from Paris Saint-Germain, with the Gunners snapping him up for only £500,000.
The Frenchman, who was 17 at the time he signed for Arsenal, was Wenger’s first official signing as Gunners boss.
Anelka made only four Premier League appearances in his debut season for Arsenal after arriving in the second half of the 1996-97 campaign.
However, the former Arsenal and Chelsea striker secured more regular playing time in the following season after Ian Wright was sidelined due to a long-term injury.
Anelka showed exactly why Wenger rated him so highly in the 1998-99 season by scoring 17 times in 35 Premier League appearances, but the Gunners fell a point short of United in the title race.
Image credit: PA
The former France international, who finished the aforementioned season as Arsenal’s top scorer, would be voted the PFA Young Player of the Year.
Anelka would force a £22.3m move to Real Madrid in 1999, despite Wenger’s desire to keep him in north London.
He was famously nicknamed ‘Le Sulk’ and claimed that he was “bored” with life in London, with Arsenal using the funds from the Anelka deal to sign Henry.
Anelka went on to play for 11 clubs after his time with Arsenal, including a second spell with PSG.
The former Manchester City and Madrid man retired from football in 2015 after spending two seasons with Indian Super League side Mumbai City.