This paper discusses the historical development of the Greek negator system, from Homeric Greek to Standard Modern Greek, in connection to the Jespersen’s Cycle phenomenon (Jespersen 1917, since Dahl 1979) and proposes a broader approach for Jespersen’s Cycle: an approach that is inclusive both to traditional Jespersen’s Cycle languages (Van der Auwera 2009), as well as atypical Jespersen’s Cycle languages. Greek is among the latter, along with languages that deviate in one way or another from what the current understanding of Jespersen’s Cycle predicts. The proposed approach views Jespersen’s Cycle as a phenomenon that targets intensified predicate negation and with time elevates it to propositional. This view agrees with current theories of grammaticalization and syntactic change (Roberts and Roussou 2003, Van Gelderen 2004), while the schematic representation of Jespersen’s Cycle is given as an instance of upward lexical micromovement (Chatzopoulou 2012).