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#5 Antonio Cassano-2006
After five successful years with the Italian club Roma, Antonio Cassano was signed by Spanish giants Real Madrid for a fee of £3.8m in 2006.
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Though he was a player of immense ability and supremely talented, has had a poor attitude in the past and has clashed with teammates and managers in some of his previous clubs.
It took the Italian just over three minutes to score on his debut after he came off the bench as a replacement against Real Betis. But in spite of the promising start, Cassano's attitude and refusal to train hindered his rise in the club.
Despite the hefty fines made by the club on Cassano for lack of discipline, he continued to cause more trouble and in a result, he was suspended for "A lack of respect" in 2006 and was subsequently dropped.
Due to this, Cassano was packed off from Madrid after only one and a half seasons with the club, to join Sampdoria, initially on loan and then on a permanent basis in 2008.
However, the 33-year-old Cassano's attitude problems didn't solve in Sampordia due to which he made his final move to AC Milan in 2011 before retiring in 2017.
