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AC Milan’s Notable Managers 

Since its founding in 1899, AC Milan had a colorful history of its own as one of the biggest names in Italian football. 

Countless managers have left an imprint beyond the San Siro and the Milanello, as they won more than just matches and silverware along the way. In their time managing the Rossoneri, they have influenced the direction of the fabled club. 

Nereo Rocco 

The club’s winningest coach, Rocco made catenaccio mainstream as he was one of its main proponents. During his three separate spells from 1961 to 1977, he brought 10 titles to the San Siro, half of which came from his second stint. 

He won a pair of Scudetti and three Coppa Italia as his domestic haul, before making his name outside of Italy, where he won a pair each of the European Cup and the European Cup Winner’s Cup, as well as the 1969 Intercontinental Cup on his tenure. 

Arrigo Sacchi 

The shades were a perfect representation of Sacchi, who was the anti-thesis of Rocco in more ways than one, as he took up coaching after selling shoes for a living.  

Apart from his attacking philosophy, he innovated Italian football with his use of the high pressing and the offside trap. His Rossoneri not only has the fluid yet solid defensive wall of Maldini and Baresi, but also a fearsome attacking trio from the Netherlands: Ruud Gullit, Frank Rijkaard and Marco van Basten. 

Signed during the early days of Berlusconi’s ownership in 1987, he won eight trophies during his first stint, where he had been known as the manager of the Milan side that won back-to-back European Cups from 1989 to 1990, before leaving the following year to become the Azzuri manager. 

Fabio Capello 

He might have just improved Sacchi’s style while being pragmatic, but Don Fabio made Milan more creative in his squad approach, during which he rotated his first team not just to keep them fresh for the big games, but also allowed more freedom apart from their roles. 

It was his versatility and adaptability to situations that made him the second-winningest manager in the San Siro with nine trophies in the 90s, including four scudetti. His 1991-92 side were the third Italian club to win the domestic league unbeaten (doing so in 34 matches). Also, he added a Champions League to his name in 1994 with a four-goal demolition of Barcelona in Athens. 

Carlo Ancelotti 

It is fitting to put a disciple of both Sacchi and Capello to this list, in which his winning experience in playing for both managers became his guide when he first came to the San Siro as their new boss in 2001. 

Ancelotti became the record holder for most games managed, which was 97 more than the fabled Nereo Rocco. During his eight years until 2009, he managed to win eight trophies, including two Champions League titles, while employing the same creative philosophy that he had during his playing years. 

His Milan squad not only had former teammates Costacurta and Maldini leading the back in the twilight of their careers (alongside goalkeeper Dida) but had a plethora of players that enabled him to play his preferred tactics. This generated the rise of the likes of Andrea Pirlo, Ballon d’Or winner Kaka, and the attacking pair of Inzaghi and Shevchenko.