Cesare’s playing days with Milan came to an end in 1966, but just six years later he was back, and this time on the bench, guiding the side in the Cup Winners’ Cup versus Red Boys of Luxembourg in a 4-1 victory and with the great Nereo Rocco as technical director. As a true Milanista however Cesare also experienced the lows such as the defeat to Verona in 1974 and the club ushered in Giovanni Trapattoni for the remaining games of the season. But his bond to Milan was unbreakable and what’s more, there would be a second generation with his son Paolo following in his footsteps and enjoying unrivalled success at the club.

After his experience as Italy coach at the World Cup in France in 1998, Cesare returned to the Milan family as head scout and in March 2001 he took over from Alberto Zaccheroni for the closing stages of 2000-2001 season, overseeing the memorable 6-0 victory over Inter. There are also high hopes of a third generation as his grandson Christian is now back in form again after recent injuries and impressed at the recent Viareggio Cup, the prestigious youth tournament, with the Milan Primavera (U19s).

The club president Silvio Berlusconi and the rest of the club will always remember fondly his charisma, kindness and warm smile. The club sends its condolences to the Maldini family and the loss of such a key figure in Rossoneri history has left everyone at AC Milan moved and saddened.