The transfer market of Milan is heading back to South America once again with the proposed signing of Boca Juniors midfielder Rodrigo Bentancur. The rossoneri have had a love/hate relationship with the country with many players arriving at Milanello but not all of them able to succeed.
 

This summer, the rossoneri could see three new editions from over there; Bentacur is one and he will follow in the footsteps of Leonel Vangioni (River Plate) and Gustavo Gomez (Lanus). It’s hoped that these players make a better impression than the last two players to head over, defender Jherson Vergara and midfielder Bruno Montelongo. Both players had short-lived careers at Milan with both disappearing without a trace due to the arrivals of Ibrahimovic, Robinho, van Bommel, Boateng and Cassano.  

To find one of the best purchases by Milan from South America in recent years we have to go back to the 2008-09 season when Galliani managed to pick up Thiago Silva for just €10 million; the last great defender to wear the rossoneri jersey. During that same summer, two players from Uruguay arrived in the shape of Mathias Cardacio (Nacional) and Tabaré Viudez (Defensor). A year previous to that, a young striker called Pato arrived from Internacional whose career was beset by injuries despite being a darling of the rossoneri faithful during his time at the club. Other names all came and disspeared without a trace; who remembers Grimi, Marcio Amoroso and Diago (the brother of Kaka)? Goalkeeper Dida’s arrival in 2003 from San Paolo, shortly after the club had been crowned champions of Europe, had a great opening two years at the club despite never really endearing himself to the fans at the San Siro. Derided by many, including Luciano Moggi at Juventus, he went on to win one scudetto, a Champions League, a European Supercup, a World Club Championship and a Golden Ball in 2007.

By Daniele Polidoro. Adapted and translated by Steve Mitchell