#1 Kaka – Real Madrid
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Arguably one of the worst ever transfer decisions, Kaka literally threw his career down the line when he left AC Milan for Real Madrid to become a centrepiece of Florentino Perez’s Galaticos 2.0 back in 2009. During his time at Milan, Kaka was one of the best playmakers in the world and was a pivotal part of the Milan sides that dominated both Italy as well as Europe.
He won the Serie A player of the year award in his debut season with the Italian giants and quickly established himself into a midfield that boasted of names like Gennaro Gattuso, Clarence Seedorf and Andrea Pirlo.
In 2009, Kaka completed a €65 million move to the Bernabeu but failed to fulfill his expectations due to repeated injuries and a few performances that let him down. Soon, he was deemed surplus to the requirements and was offloaded to Milan in 2013 after a disappointing spell with the Los Blancos.
The Brazilian failed to recapture his form thereafter and is currently plying his trade in the MLS with Orlando City. He also made a return to Sao Paulo, where he started off as a player, in a loan spell but has looked nothing like what he was during his prime years in Italy.
