Andrea Pirlo was one of the greatest midfielders of a generation full of sensational midfielders. The Italian was an absolute maestro in the middle of the park and it would have been fun to see what he could achieve in a Real Madrid shirt. A move to Santiago Bernabeu did not end up transpiring though.
Pirlo would spend almost his entire playing career in Italy, representing clubs like Inter Milan, AC Milan and Juventus, before making a move to the MLS to play for New York City FC in the twilight of his career.
Thus, we do not know how Pirlo would have fared in a foreign league. It appears that a move to Real Madrid did come pretty close to happening after the 2006 World Cup though, which Italy won.
Pirlo has now shed some light on why the move to Real Madrid did not happen and he decided to stay on at AC Milan. As reported by FourFourTwo, the Italian legend said:
"“We had just won the World Cup, but we didn’t know what would happen.“I was very, very close with Real Madrid, but then we got told that Milan could enter Champions League qualifying and be readmitted to Serie A. I was offered a new contract straight away and the club did a lot to keep me.”"
Pirlo reveals why Real Madrid move did not happen after World Cup win
Real Madrid would end up signing Fabio Cannavaro after the 2006 World Cup but could not manage to get their hands on his Italian national teammate. AC Milan were in deep trouble at that time due to the Calciopoli scandal and there were question marks about whether they would even remain in the Serie A and Champions League or not. When they retained their status, Pirlo remained with Rossoneri.
One of the greatest things about Pirlo was his incredible longevity, as he managed to adjust his game accordingly to his age and remained one of the best midfielders on the planet, very late into his career.
In fact, one could make the argument that he started to earn the plaudits that he deserved pretty late into his career and was not recognised as one of the classiest midfielders in the game by many, till the 2010s.