Massimo Ambrosini is an Italian former professional footballer, who played mainly as a defensive midfielder. At club level, he is best known for his fruitful time with AC Milan, where he spent a remarkable eighteen years of his career, captaining the side from 2009-14 and winning several titles. At present Massimo works as a football commentator and pundit commentator for Sky Sport in Italy.
Ambrosini started his career with Cesena, graduating to their first team during the 1994-95 season by the age of 17. He was signed the following year by Milan’s Capello and made a number of appearances as the squad progressed to the Serie A championship. After a brief stint with Vicenza during the 1996–97 season where he played a pivotal part in the team reaching the semi-final of UEFA Cup Winners’ Cup. Ambrosini returned to Milan until 2014, where he made 344 appearances for the side. The 2006-07 season was pinnacle for him as he played a crucial part in the final of the Champions League victory against Liverpool.
In 2014 Ambrosini retired from professional football after a season with Fiorentina. At international level, he represented Italy in two UEFA Championships, acquiring a runners-up medal at the UEFA Euro 2000, as well as the 2000 Summer Olympics.