[[1]] In 1976, he was sold to Napoli in an exchange bid with Giorgio Braglia,[1] with whom he shared the same nickname: Cavallo Pazzo ("Crazy" or "Mad Horse", in Italian).

Chiarugi also gained three caps for the Italy national football team, making his debut on 22 November 1969 in a 3–0 win over East Germany.

[2][4] Known in Italian football for his impetuous nature, pace and technique, which gained him the nickname Cavallo Pazzo (Crazy Horse), Chiarugi was a quick, energetic, and highly creative forward with an eye for goal and excellent dribbling skills, known for his individualistic playing style, as well as his use of elaborate feints and nutmegs to beat opponents.

[2][7] In February 2001, following the dismissal of Fatih Terim, Chiarugi was installed as caretaker coach for a single match, a 2–1 loss to Bari,[2][8] before the appointment of Roberto Mancini.

Following the departure of Ottavio Bianchi, Chiarugi was appointed again as caretaker coach during the dramatic 2001–02 season, which ended with relegation to Serie B and the successive club cancellation due to financial troubles, which ultimately led to Fiorentina's bankruptcy.