3. Carlo Ancelotti
Position: Central Midfield
Carlo Ancelotti began his club career with Parma in 1974 at the age of 18. His ability while in possession of the ball quickly saw him gain fame and he was signed up by Roma in ’79. What Carletto lacked in physicality and athleticism, he more than made up for with his insane technical ability, composure on the ball, and wide range of passing. Extremely versatile in midfield, he was best fielded as a deep-lying playmaker and revolutionized the role while serving as inspiration for the likes of Andrea Pirlo and Albertini. His time at the capital saw him win the Italian Championship and four Coppa Italia titles before he was signed by AC Milan. What followed was unprecedented domestic and continental success.
With Milan, Ancelotti was a part of an extraordinarily talented group of individuals which included Franco Baresi, Paolo Maldini and the Dutch axis of Marco van Basten, Ruud Gullit, and Frank Rijkaard. Carlo added balance and poise to this fearful line-up and Milan consecutive European Cup titles, two UEFA Super Cups, two Serie A titles, and two Intercontinental Italian Cups.