Guappo (plural: guappi) is a word in Neapolitan language, meaning thug, bully, braggart. While today the word is often used to indicate a member of the Camorra, a Mafia-type organisation in the region of Campania and its capital Naples in Italy, the guapperia (or guapparia; i.e., the guappo culture) predates Camorra and was originally very different.
The word derives from the Spanish guapo, meaning bold, elegant, an ostentatious person, and which eventually derives from the Latin vappa, meaning flat wine or scoundrel. The noun guapparía, which is sometimes also used to indicate the Camorra, means arrogance, domineering, braggart. The verb guappia means to behave like a guappo (Camorrista), to be domineering and derives from the Spanish guapear (to feign courage, to flaunt elegance).
The word wop, a pejorative American slang term for an Italian, probably derives from guappo.
The figure of the guappo is not necessarily synonymous with the Camorrista. It is a historical figure in the Neapolitan area, distinguishable by his smart or overdressed dandy-like appearance, his unusual pose that serves to draw attention to him, and the particular care he lavishes on his body and face. The guappo could be characterized as "simple" or "posh" according to the clothes he wore: the former preferred extravagant and flashy clothes while the latter loved to dress in clothes from the best tailors in Naples.
Originally, the guappo was rather a violent free spirit; free from the law as well as the "official" Camorra, with his proper code of honour, at once an extortionist, a rectifier of wrong for the local neighbourhood and a benefactor of artists of the café chantant. He was sometimes allied with, and sometimes a rival of the Camorra. Around 1860, a guappo was described as an independent and individualist camorrista.
When the Camorra as an organisation was weak, the guappo flourished. After the first mass trial against the Camorra in 1911-12, and the advent of Fascist rule the Camorra as an organisation was nearly destroyed. The local guappo returned and the interwar period (1918–1939) was the heyday of the individualist guappo power. After World War II, with the return of the Camorra, the figure of the guappo eventually merged into the organisation. A typical guappo of that era was Pasquale Simonetti, also known as "Pascalone ‘e Nola", who controlled the Naples fruit market. He was married to Pupetta Maresca and famous for publicly slapping American Mafia boss, Lucky Luciano, at the Agnano racetrack. (In actual fact the perpetrator was Francesco Pirozzi, known as Ciccillo 'o francese, one of the men of Camorra boss Alfredo Maisto.)