Kaka From AC Milan to Real Madrid (2009) - $87 Million
For the middle part of the last decade, Brazilian Kaka was considered to be the true heir to Zidane, a silky attacking midfielder who glided along the pitch like he was on rails. It seemed only natural that he'd follow in "ZiZou's" footsteps and head to Madrid.
But Kaka was a different person. He was loyal and intensely religious. The money that Madrid offered him couldn't lure him away from his beloved Milan.
Finally, when Real came along with a then world record $87 million bid, AC had to convince their star to leave home.
After a disappointing spell at Madrid he was ultimately sold back to Milan on September 2, 2013, with a giant smile on his face.
