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#4 Antonio Cassano
One of the most talented players to ever play the game, Antonio Cassano spent two seasons at Real Madrid without having any sort of positive impact on the Spanish giants. Having signed for Los Blancos in January 2006 for €5 million, the Italian managed to score only 3 goals in 29 appearances. Cassano even called it the biggest mistake of his life:
“My biggest mistake was the year and a half at Real Madrid because I did everything and more to ruin it. That is a huge regret,
“I was seduced by their offer. If I had listened to Totti, I probably would’ve stayed at Roma for 10-15 years along with him. That was the advice he gave me, and I had to listen. But I did my usual, and it went instinctively to my head.”
Soon things went downhill for Cassano at Real Madrid, as he started gaining weight and struggled to get into the first team ahead of Raul and Ronaldo Nazario. His weight problems got so out of hand that Madrid even started fining him for every gram he gained over his playing weight which earned him the infamous nickname 'Gordito'.
For all his talent, Cassano never made it at Real Madrid and is considered to be one of the worst signings made by Florentino Perez.
