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This paper examines Plutarch’s ideas on political leadership and euergetism in the lives of Cimon and Pericles against the background of second-century AD city politics. Up till now, scholars have mainly explored the Lives as sources on the periods they describe or as programmes for moral self-improvement (Pelling 1995; Duff 1999; Stadter 1997, 2003-2004; Chrysanthou 2018). Recent research on the Moralia and the Lives, however, has argued that Plutarch not only intended to morally improve his readers but also to help them become more effective political and military leaders (Van Hoof 2010; Jacobs 2017). The paper proposed here aims to test the hypothesis that the lives of Cimon and Pericles were, in part, intended to instruct second-century AD politicians on how to secure and maintain the support of the dēmos through acts of munificence. Although it has been recognised that the interaction between politicians and the people constitutes an important and recurring topic in the Lives (Saïd 2005; de Blois 2008; Pelling 2011), the possible significance of these biographies for the dissemination of ideas about political leadership and mass-elite relations in Plutarch’s own day has hitherto gone unnoticed. This line of investigation is nevertheless highly relevant in light of the new, emerging orthodoxy among specialists of the imperial Greek city that emphasises the vitality of the popular assembly and an ongoing tradition of ‘people politics’ (Zuiderhoek 2008; Fernoux 2011; Oppeneer 2018, 2020). A crucial aspect of mass-elite relations in the Roman-era polis was the exchange of gifts for honours (Zuiderhoek 2009; Heller & van Nijf 2017). Unsurprisingly, then, Plutarch discusses the phenomenon at length in his Political precepts, a treatise aimed at the political leaders of his own time. Although he strongly condemns certain types of benefactions as examples of pleasure-oriented demagoguery, he also argues that a good leader should, from time to time, give in to popular demands. To support his argument, he advances Pericles and Cimon as paradigms of politicians who were able to secure the support of the people through the appropriate use of munificence (818d). Since these politicians have received a more substantial treatment in the Lives, this paper explores the possibility that Plutarch’s discussion of the euergetic phenomenon in Pericles and Cimon might, in part, have been intended to provide his readers with insights that could be applied to the politics of honour in Roman times. To this end, my paper compares Plutarch’s depiction of euergetism (Cim. 10; Per. 9, 12, 34.1) with the honorific discourse articulated in the epigraphic record of the imperial Greek cities. This comparison could shed some new light on Plutarch’s approach to political leadership and the politics of honour in the Greek cities of the Roman empire. In addition, it might show that, notwithstanding the current focus on virtue and vice, Plutarch also intended his Lives to be of practical use for the political leaders of his own time.