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This chapter shows how the elaboration of the idea of freedom and its place in modern politics has been carried out in dialogue with ancient Greek political thought, by looking at three important, yet inadequately appreciated, texts of modern political reflection. The three texts are Leonardo Bruni’s ‘Of the republic of the Florentines’ (1439), Jean-Jacques Rousseau’ s Discourse on Political Economy (1755), and Benjamin Constant’s The Spirit of Conquest and Usurpation (1813). Despite their originality and incisive argumentation, the three sources have remained in the margins of scholarship and rhetoric on the canon of modern political thought. The paper draws attention to the texts as statements of political criticism, through which conceptions of freedom are articulated in response to the challenges of modern society.