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From the political and institutional perspectives, the transition from the Roman Republic to the principatus cannot be conceived as being totally completed in the first century CE. Although power had become absolute and the princeps—the one—had achieved the strongest position, whereas both the few and the many had been gradually marginalized from ruling, this absolutism was not still completely shaped, particularly with regard to the issue of the choice of the ruler. What is shared among some political authors in this period is a focus on the lack of opportunity in playing a role in the appointment process of the princeps: the designation of the ruler is more frequently out of control of the ruled people and the spaces of maneuver within the political institutions appear drastically smaller. In this context, part of the political literature aims to fix this problem through the specula principis: if there is little space for being involved in the choice of the princeps, it becomes essential to influence the ruler and/or the possible successors with a view to allowing them to be good governors and not cruel tyrants. This essay analyzes, in a comparative perspective, the prince’s educational plots in the Plutarchan political Moralia, the Discourses on Kingship by Dio Chrysostom, and the De clementia by Seneca, in order to stress the elements of continuity and discontinuity among these works with particular regard to their respective educational solutions to the twofold crucial problem of having a good princeps and avoiding tyranny.