This chapter explores the ideas behind Niccolò Machiavelli’s two major political works, Discourses on Livy and The Prince. It starts by explaining how Machiavelli’s reception and biography highlight a correlation between his activities as Secretary of the Florentine chancery and his later theoretical work. Machiavelli’s philosophical thought primarily focused on power and the state; whereaa, his theory of history introduced the concepts of virtù (virtue) and fortuna (fortune). The chapter also outlines Machiavelli’s understanding of republican freedom in line with the significance of the conflict between the few and the many. Finally, it raises issues of violence, conquest, and empire correlating to Machiavelli’s theories.