Nicolas Anelka
In: £500k Out: £22.5 million
One of the many players in the Arsenal squad who were of French origin, Anelka was picked up from Paris Saint-Germain’s youth squad, at the age of 16. Bought for £500k by the newly-appointed Wenger, his potential as a striker was huge. After waiting on the sidelines for his first year, Anelka quickly found his feet, scoring his first against Manchester United in a 3-2 win at home.
He played a vital role in the double that year, scoring a decent 9 goals in 40 appearances in all competitions, but he quickly became persona non grata due to reported lack of enthusiasm and a negative attitude. The fans named him ‘Le Sulk’, and he left the following summer for Real Madrid for £22.5 million. Persistence and consistency are the last words you will choose to describe the man, as he has since been a part of 9 different clubs. He wasn’t the best buy in terms of the goals he scored; but in terms of cold hard cash, this was a brilliant bargain. Also, do keep in mind that Wenger was quick to get rid of a player who proved his critics right with his antics on and off the field. He was a talented player for sure, but certainly not the best example for his teammates.