I think we can all agree Ashley Cole was the biggest loss 26 years old when he left, arguably the worlds best left back for a long period of time, he would have eventually gone on to be our captain.
Cant believe we sold him to our wealthy rivals but 5M + Gallas, we should have been demanding at least 40M at the time. The sad thing is this was all for the sake of 5K wages which he no doubt deserved fast forward a few years and we give out big contracts to hype merchants like Jack Wilshere and Walcott.