In 2011, Milan decided not to renew Andrea Pirlo’s contract. He was 32 years old and, for the club, his best days seemed to be behind him. Allegri did not see him as an indispensable piece either.
Pirlo felt that Milan no longer trusted him and made a decision that would change history: he left for Juventus, their crosstown rival, on a free transfer.
What happened next was Milan’s worst nightmare. Pirlo became the brains behind a Juventus side that dominated Italy, was named Serie A’s best player, and won four consecutive Scudettos.
Every time he faced Milan, the man they considered “too old” was on the other side. Years later, Adriano Galliani admitted it bluntly: “It was the biggest mistake of my career”.
Milan thought Pirlo was finished at 32. Pirlo made sure to prove to them that they had simply let go of a champion who still had a lot left to win.