|Date of birth||23-05-1961|
|Seasons in Monza||1978-1981|
|Caps and goals||60(10)|
It was launched by Monza in Serie B in 1978, playing three good seasons. He moved to Serie A in 1981, making his Serie A debut on 13 September 1981 against Como. Just ten days later he made his debut in the Under-21 national team, with which he will play a total of 4 games, scoring a goal.
With the purple jersey he immediately became the owner and fought for the league title until the end: the title faded by only one point and Juventus won it. On 14 April 1982 he made his debut in the senior national team, in the defeat against East Germany (in the same game another young man, the Interista Giuseppe Bergomi, made his debut). Enzo Bearzot calls him to the 1982 World Cup, where he will graduate world champion without playing any games.
In the following years he only plays sporadically with the blue shirt while he becomes a regular holder of the Florentine team until 1986, when he is bought by Milan. With the Rossoneri shirt he won the 1987/88 championship, but was transferred the following year on loan for a season to Roma, as it was not very appreciated by the Rossoneri coach Arrigo Sacchi. Back in Milan, after Arrigo Sacchi saw him again in the Rossoneri shirt, in 1989/1990 he scored 10 goals and won the Champions Cup: although he never has the certainty of being a holder, he often finds space in the Milanese team. He becomes an even more important pawn in the team's game with the advent of the new coach Fabio Capello, who, after the injury of Van Basten and the sale of Papin, makes him play in the new role of center forward. Massaro adapts perfectly, given his offensive characteristics, and in 1993/1994 leads the team to the third consecutive championship, becoming the idol of the fans, who nickname him "Providence". In addition, in the Champions League final in Athens against Barcelona, ??he is the star of the evening making the first two goals that stretch the Blaugrana.
His old coach Arrigo Sacchi then calls him into the national team for the 1994 World Cup: Massaro scores a very important goal in the first round against Mexico which will allow Italy to go to the round of 16. Deployed in the final against Brazil, he has the opportunity of the knockout but is unable to exploit it. On penalties (of which Massaro will miss the fourth penalty of the unfortunate series) then Italy succumbs to the Brazilians who graduate world champions.
THE END OF THE CAREER
After the World Cup he played for another year at Milan, but he proved to be in a downward parabola after having lived a second youth at the age of 34: he therefore moved to Japan, in Shimizu S-Pulse, where he ended his career . Back in Italy, he is now head of Milan's PR and a television commentator. He is also an excellent golfer. He is currently a regular guest at the production of RAI International, "The joust of goals", where he comments on the most important matches of the day.