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Good citizens of a republic should be capable of ruling and being ruled in turn. Appealing as it may seem, this prescription faces the practical problem that ruling and being ruled often require from citizens qualities and dispositions incompatible with one another. In an imperfect republic, this problem appears in an even thornier form: citizens who wish to establish a just rule cannot avoid standing up to the unjust rule of the present, but their successful resistance may weaken the authority of the rule that they establish—either by igniting their own ambition to usurp this rule for their own sake or by setting an example for their challengers to fiercely resist this rule. In this paper, I examine Machiavelli’s account of the love of honor and glory, a passion that has often been misunderstood as the equivalent of ambition, as one of his solutions to this problem of political ethics. Developed largely from his understanding of the practice and ethics of war, Machiavellian honor not only is compatible with his view that human beings are primarily motivated by interests and passions, but also solves two difficulties found respectively in Ciceronian honor and chivalric honor: while the former underestimates the difficulty of resisting the existing rule, the latter—as Machiavelli understands it—exacts from citizens too much obedience to the existing rule. Striking a balance between their political entrepreneurship and rule-abidingness, Machiavellian honor motivates citizens and would-be civil princes to not only accept the importance of not being good when necessary but also refrain from committing unnecessary evil. Finally, I examine Machiavelli’s own qualification for his positive appraisal of the love of honor and critically assess the applicability of Machiavellian honor to the political ethics of citizens in contemporary constitutional democracies.