8) Nicolas Anelka – 1999
The France international proved to be arguably Arsene Wenger’s best bit of business. Having bought the forward for ÂŁ500,000 from Paris Saint-Germain, the Frenchman was sold a year later to Real for ÂŁ23 million – buying none other than Thierry Henry as his replacement.
After initial success, he fell out of favour with the fans, players and coach Vicente del Bosque. But luckily for Los Blancos, PSG were prepared to pay all ÂŁ23 million Real spent on bringing him in from north London in the first place.
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