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This study seeks to investigate a connection between the political thought of Machiavelli and the philosophy prevalent in the work of Girolamo Savonarola. In this consideration, it will be necessary to examine the works of Savonarola. After considering Savonarola, the study focuses on Machiavelli and apparent similarities between the two men’s writings. In addition to cross-referencing Machiavelli and Savonarola, it is necessary to cross-reference the work of Machiavelli with other humanist sources to determine whether or not Machiavelli’s alternative perspectives of human nature can be synthesized into the larger context of the scholarship of his day. For this purpose, the works of Coluccio Salutati and Desiderius Erasmus are examined as representatives of two different cross sections of Renaissance culture and literature. This examination seeks to focus emphasis on the similarity between Machiavelli’s writing and Savonarola’s preaching.