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This article aims at investigating some diachronic aspects of the Italian negative system, considering a time span ranging from Old Latin to Modern Italian. Most of the negative polarity phenomena populating the Modern Italian system are consequences of a crucial change that occurred in Old Latin: The Latin negative morpheme <i>nōn</i> (“not”), which initially displayed a maximal projection status, and became a syntactic (negative) head. This change caused the shift from a double negation system to a negative concord one, which affects many Romance languages (and their dialects). It also determines the availability of the expletive reading of negation in Italian, as well as in other Romance languages (ex. French), calling for a new generalization: only languages (and structures) displaying a negative head allow the expletive interpretation of negation, languages displaying a maximal projection status do not.