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The sale of Ricardo Kaka to Real Madrid seven years ago today was a difficult one for fans of the Rossoneri as their “Prodigal Son” had departed. Since his sale, success has been hard to come by in the fashion capital of the world for the red and black.

On this day in 2009, A.C. Milan’s star Brazilian Ricardo Kaká was sold to Real Madrid in what was – at the time – the second-largest transfer in world football history at 65 million euros behind Zinedine Zidane’s 75 million move. It wasn’t only until the Merengues one-upped their haul by landing Cristiano Ronaldo from Manchester United that same summer for €94m.

Kaká’s historic Milan career began back in 2003 when the club purchased the gifted Brazilian from São Paulo for an estimated fee of 8.5 million euros; a bargain to say the least. His achievements with the Rossoneri include the following: one Serie A title (2003-04), one Italian Super Cup (2004), one UEFA Super Cup (2007), one UEFA Champions League title (2006-07), one FIFA Club World Cup (2007-08) and of course a Ballon d’Or in 2007; the last player to win the honor not named Ronaldo or Messi.

The 34-year old Orlando City SC playmaker appeared in a total of 120 matches for Real Madrid, scoring twenty-nine goals and tallying thirty-nine assists respectively. Injuries plagued him quite a bit in Spain before he made his return home to where he was most successful in September of 2013.

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