The present research investigation concentrates on Xenophon’s historiographical works, focusing in particular on those minor figures in them who display characteristics or behaviour that render them unworthy of the governing role they occupy. Critics have long focused on identifying and analysing those characters who represent the perfect model of leadership described by Xenophon and offered for imitation by his audience. However, very little has been said about the opposite figures, those paradigms and opposites, destined not so much to be imitated, but rather useful in representing the mistakes that a reader must avoid and to bring out even more the models of enlightened and capable leadership that are the real focus of Xenophon’s attention in various works. If, in fact, the paideutic intention and characteristics of the Senofonte corpus is evident, intended to teach the qualities, political but even more so moral, necessary to hold a role of government and leadership; it would seem logical to assume that this didactic purpose of Xenophon’s works can also be realised in the negative figures, whose role is emphasised and highlighted by the author through ever new literary strategies.