Born in 1966, Alessandro Costacurta is considered as one of the best defenders to wear the legendary AC Milan shirt. He spent over twenty years with Milan between 1986 and 2007 during his club career, as well as a brief season-long stint on loan at Monza. He is best known for his role alongside Franco Baresi, Paolo Maldini and Mauro Tassotti during the late 1980s and 1990s. He played under the crème de la crème of managers, such as Arrigo Sacchi and Fabio Capello where he formed one of the greatest defenses in Serie A and European football.
In 1987 and on matchday 6 of the season, Costacurta made his first Serie A debut on October 25th against Hellas Verona. Milan would go on to win the game 1-0, as well as the Serie A title, but due to the presence of the more experienced Filippo Galli in his place, Costacurta received minimal playing opportunities that season. With the Rossoneri, Billy (as nicknamed by the fans) won the following 7 Serie A titles, 1 Coppa Italia, 5 Supercoppa Italiana, 5 European Cup / UEFA Champions League, 4 European Super Cup / UEFA Super Cup and 2 Intercontinental Cups.
Following his retirement, Costacurta formed part of Carlo Ancelotti's coaching staff in Milan as a technical assistant in 2008, thus receiving his own coaching badges. He was employed as a football pundit by Sky Italia in 2010, becoming one of the TV channel's top sports stars and being featured in several of the channel's shows till present.