Kaka to Manchester City
Manchester City made a reported £100 million bid to sign Kaka from AC Milan in the January transfer window of 2009. If that deal had been completed it would have almost doubled the world record fee Real Madrid had paid to sign Zinedine Zidane from Juventus.
Kaka eventually joined Real Madrid that summer for a then record high of £56 million, which was soon dwarfed following the acquisition of Cristiano Ronaldo. The Brazilian, though, never made his mark at the Santiago Bernabeu.
Injury problems and a loss of form made for a relatively underwhelming stay in Madrid when considering the fee paid to sign him, and Kaka left the club after four seasons, rejoining Milan on a free.