Answer
During his time at AC Milan, Massaro was managed by Arrigo Sacchi and Fabio Capello. Sacchi is widely regarded as one of the greatest managers of all time, having led Milan to European Cup success in 1989 and 1990, as well as the Intercontinental Cup in 1989. Capello was also a highly successful manager, winning three Serie A titles with Milan and the Champions League in 1994.