#3 Ashley Cole
Ashley Cole was the poster-boy dream for any young football fan – the Arsenal fan who made it through his club’s academy and became a legitimate star featuring in the greatest team of his club’s history. Yet, Cole found it fit to flirt with Chelsea after Arsenal offered him a poor wage increase in contract negotiations.
Ultimately, Ashley Cole left Arsenal with William Gallas moving from Chelsea in a cash plus swap deal. At the time, it was considered a coup for Arsenal, but Gallas proved to be one of the most poisonous captains Arsenal have ever had, overseeing a side that had frequent infighting and collapsed when things became tough.
As for Cole, he racked up the trophies with Chelsea, going from strength to strength as he cemented his status as the best left-back in the league. Had the Gunners kept him, Cole would still have been the best left back in the league, while Arsenal might have also won a trophy or two with him at the Emirates.
