#4 Ashley Cole
One of the most controversial exits from Arsenal took place in the summer of 2006, as left-back Ashley Cole – who broke through into the Gunners’ first team from their academy in 1999 – moved to Chelsea following some protracted negotiations that went back well over a year. In the aftermath of the move, Cole became one of the most hated players in Arsenal history and was even christened ‘Cashley’ by fans who felt that the move was driven purely by greed.
The controversy started when Cole was caught in a secret meeting in early 2005 with his agent, Jonathan Barnett, Chelsea manager Jose Mourinho and their chief executive Peter Kenyon to discuss a move – all while he was under contract with Arsenal. The Premier League found all parties guilty of illegal “tapping up”, and all 4 men were fined. The relationship between Cole and Arsenal essentially never recovered.
Despite signing a contract extension with Arsenal later that summer, a year later he was gone, heading to Stamford Bridge for a fee of £5m, with Chelsea defender William Gallas moving in the opposite direction.
The move was bad enough for Arsenal fans, but their opinion of Cole being greedy was made even worse when he released his autobiography, stating he was left “trembling with anger” when Arsenal only offered him £55k per week, while Chelsea were willing to pay £90k per week.