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In the Florentine Histories, Machiavelli presents Giano della Bella and Michele di Lando as well-intentioned leaders who fail to imitate the ancient examples of Moses, Romulus and Brutus; consequently, they fail to become successful founders or reformers of the early Florentine Republic. Machiavelli suggests that naïve or undifferentiated notions of goodness or patriotism prompt Giano and Michele to spurn the common people’s support, to exhibit excessive deference to rapacious elites and, eventually, to exit the city—leaving it much worse off than before (FH III.13, 22). In this paper, I show that Machiavelli’s accounts of more cravenly ambitious Florentine figures, Corso Donati and Walter Brienne, evince defective notions of self-interest that prevent them from acting in ways that could have benefitted Florence’s civic and geo-political welfare—as well as their own political reputations and authority. Machiavelli indicates that Corso and Walter both arouse harmful popular hatred against themselves rather than inspiring salutary popular respect; they neglect to organize widely public, civic-military forces rather than merely sectarian ones; and they both rely too extensively on foreign support for their defectively established authority (FH II.21, FH II.33-34). Machiavelli declares that a “wise legislator” could have imposed a proper constitutional order upon the Florentine Republic (FH III.1). Nevertheless, both Florence’s well-meaning and selfishly motivated leaders, Machiavelli reluctantly shows, consistently facilitate a significant deterioration of liberty in his native city.