Massimo Ambrosini (Italian pronunciation: [ˈmassimo ambroˈziːni]; born 29 May 1977 in Pesaro, Marche) is a former Italian professional footballer, who mainly played as a defensive midfielder. At club level, he is mostly known for his successful time at Italian team A.C. Milan, where he spent eighteen years of his career, winning several titles, and captained the side from 2009 to 2013 following the retirement of Paolo Maldini. Ambrosini retired from professional football in 2014, after a season with Fiorentina. At international level, he represented Italy at the 2000 Summer Olympics, and in two UEFA European Championships, winning a runners-up medal at UEFA Euro 2000. He currently works as a pundit and football commentator for Sky Sport Italia.