A player that graduated through the Gunners’ famed academy system left for Chelsea in 2006 after being unable to agree a new contract

Arsene Wenger bought and sold many world-class players during his 22-year reign as Arsenal manager, but the Frenchman admits that losing Ashley Cole to Chelsea is his biggest regret as the Gunners made a rare “mistake” in the transfer market.

A home-grown product of the club’s famed academy system took in 228 appearances for the north London outfit after stepping onto a senior stage, claiming two Premier League titles, three FA Cup crowns and the first of his 107 caps for England.

Widely regarded as the best left-back in world football when performing at the peak of his powers, Cole became a superstar at Arsenal but made a controversial switch to Chelsea in 2006 after Wenger and Co were unable to agree a new contract.

There is still a sense of frustration on Wenger’s part that the Gunners were unable to retain Cole’s services as, unlike other players that slipped the net, he boasted strong emotional ties to the club.

Asked by beIN Sports on his biggest regrets on the sales front, Wenger, who walked away from Emirates Stadium in 2018, said: “I would say, most of the time the players gave us seven, eight, nine years and left after.

“The younger generation, like [Cesc] Fabregas, we lost early and would not have loved to lose him.

“The player who I think internally was a mistake to lose was Ashley Cole because he was playing at nine or 10 years old for the club.

“I knew that Fabregas, taking him away from Barcelona, at some stage he would want to go back to Barcelona. But Ashley Cole came out of the club and I think it was a misunderstanding for a few thousand pounds.

“At the time, it was when [Roman] Abramovich came in to the game and Ashley Cole is one of the few players that developed even more and continued to develop when he left.”

Cole went on to claim another Premier League title and four more FA Cups with Chelsea, along with League Cup, Champions League and Europa League triumphs.

He took in 338 appearances for the Blues before leaving to link up with Serie A side Roma in the summer of 2014.

Bridges have never been rebuilt with those at Arsenal, with many supporters accusing him of greed when crossing London, and the most-capped full-back in English football history is now working as an assistant to former team-mate Frank Lampard at Everton.

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