A star for the Rossoneri before son Paolo went on to become a legend in his own right, the native of Trieste started his career for his hometown club at the age of 21 before joining the Diavolo.
Maldini played for Milan from 1954 to 1966, helping the club win four Scudetti along with their first European Cup which came via a 2-1 win over Benfica in 1963.
After captaining the club, the Italian moved to Torino before bringing an end to his playing career in 1967.
Maldini continued his association with the game by moving into the coaching ranks, becoming an assistant for Milan before taking over as boss from 1972 to 1974.
After once again becoming an assistant, this time for the Italian national team from 1980 to 1986, Maldini then took over as coach of the U21 side.
There the tactician led the Azzurrini to three consecutive European U21 titles in the 1990s, developing future stars such as Fabio Cannavaro, Gianluigi Buffon, and Francesco Totti before eventually taking over the reigns with senior side for the 1998 World Cup.
Maldini then became Paraguay national team boss in 2001, leading them to the World Cup in 2002.
Most recently Maldini served as a pundit for Al Jazeera.