6. Ashley Cole
Enjoy that break, Arsenal fans? Considered by many as the transfer that left the most bitterness in Arsenal hearts, betrayal was certainly the word used when Ashley Cole left north London for the much larger amount of money on the table  over at Stamford Bridge.
At the time considered one of the key members of the ‘Invincibles’ and one of the best full backs in England, so it was no surprise when Arsenal fans began to refer to the England international as ‘Cashley’, in reference to the belief that his decision to move to West London was purely because of all the 0’s on the end of his proposed wage.
Take another breath, Arsenal fans.
5. Eric Cantona
Widely considered as one of Sir Alex Ferguson’s best pieces of business while at Old Trafford, this was a shocking transfer that cost around 1 million, resulting in Manchester United’s attack getting a huge boost, by bringing in Eric Cantona.
Leeds had just won the First Division title in 1991/92, before Cantona departed to help Man United win the inaugural Premier League, and become the first player to win back-to-back titles with two different clubs.
And, in case you didn’t know – Manchester and Leeds don’t like each other very much.
Table of Contents
