Career
Player
In 1976 he was sold to Napoli in an exchange bid with Giorgio Braglia. He played two seasons with the azzurri, winning a Coppa Italia and an Anglo-Italian Cup. He played for Serie B team Sampdoria in 1978-1979, and then back to Serie A with Bologna the following season.
After spells with minor league teams Rimini, Rondinella and Massese, Chiarugi retired from football in 1986.
Known in Italian football for his impetuous nature which gained him the nickname Cavallo Pazzo (Crazy Horse), he was also popularly considered as a diver, causing the Italian media to create the Italian neologism chiarugismo, a synonym of "football diving", after his name. Coach
After his retirement as a player in 1986, Chiarugi joined Fiorentina youth team coaching staff
In his career, he served as Fiorentina caretaker coach three times. Late in the 1992-1993 season, Chiarugi (jointly with Giancarlo Antognoni) replaced Aldo Agroppi with little fortune, as he did not manage to save them from relegating to Serie B after 54 consecutive seasons in the top flight.
On February 2001, following the dismissal of Fatih Terim, Chiarugi was installed as caretaker coach for a single match, a 2–1 loss to Bari, before the appointment of Roberto Mancini.
Chiarugi was appointed again as caretaker coach during the dramatic 2001-2002 season ended with relegation to Serie B and the successive club cancellation due to financial troubles. On November 14, 2007 he was announced as new head coach of Tuscan Serie C2 side Poggibonsi. He was sacked on September 2008 due to poor results.