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This thesis tracks changes in political thought in the writings of Niccolò Machiavelli and Francesco Vettori between 1512 and the 1520s. While modern historians have traditionally emphasized the early phase of their correspondence, I examine two often overlooked sources from later years: the letters they exchanged in the 1520s and Vettori's history, the Sommario della Istoria d'Italia. By the 1520s, the Italian political terrain had experienced sweeping and devastating transformations. I seek to explore the effects of those changes on these Florentines' thinking by highlighting an idea common to both of their writings-Italia. Through contrast with Vettori's thought, I contextualize the nature of Machiavelli's political observations after he had spent a decade and a half in political exile, while also shedding light on the dynamism of Italia in early sixteenth-century political discourse and historiography. In a short epilogue I suggest some ways in which a rethinking of early modern perceptions of Italia can also contribute to modern theoretical debates about the meaning of "nation."