Ashley Cole
In 2005, Cole became embroiled in one of the nastiest cases of tapping up in Premier League history and became forever known as the ultimate Judas in world football.
Along with his agent Jonathan Barnett, Cole broke Premier League rules and ethics by secretly meeting Chelsea manager José Mourinho and chief executive Peter Kenyon to discuss a transfer to Chelsea. When it came to light, Arsenal were furious and the FA fined Cole £100,000, Chelsea, £300,000, Mourinho £200,000 and Barnett £100,000, with his agents licence suspended for 18 months.
With things so sour at Arsenal he ended up leaving for Chelsea and had a successful career at Stamford Bridge. However, although he is hated now, the former academy star and boyhood Gunners fan was of our best ever players and a stalwart at left back in one of our most successful eras.
It was gutting to lose him to for the sake of an extra £10,000 a week in wages and he was a player who realistically, until Nacho Monreal, hadn’t been properly replaced.