2. Nicolas Anelka

There were no questions around the talent of French striker Nicolas Anelka when he made his big move to Real in the summer of 1999 for a big fee of £22.3m, but there were certainly questions around his attitude and temperament. The Frenchman had scored 17 goals in 35 Premier League games for Arsenal in 1998/99, but had also shown such little enthusiasm at the club that the British press had labelled him Le Sulk.
Unfortunately for Los Blancos, Anelka’s attitude didn’t especially change despite finally getting the big-money move he’d always craved. It took him six months to score a goal for his new club, and while it was an important goal – it came in a 3-0 victory in El Clasico against Barcelona – just a month later he found himself suspended for 45 days following a refusal to train.
Apparently the Frenchman had fallen out with head coach Vicente Del Bosque, and to make matters worse, he claimed the club had “treated him like a dog” by suspending him. Real’s President Lorenzo Sanz responded by suggesting Anelka had psychological issues; “something does not turn around properly in his head” was the quote uttered by the Spanish businessman.
It came as no surprise then when the striker was unceremoniously sold to Paris St. Germain in the summer of 2000; the only shock was that Real were able to recoup £22m for him. His time at Real Madrid ended with just 7 goals in 31 appearances, making him one of their most disastrous signings.