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In the philosophical system of Charles de Bovelles, figurative images play a fundamental role. These images are speculative instruments through which the philosopher unfolds his metaphysical concepts in a figurative mode. This article takes an in-depth look at three Bovillian figurative-speculative images present in De nihilo and De sapiente in order to understand the reception of Nicholas of Cusa’s thought in Bovelles’s philosophy and also to underline the fundamental differences with Giordano Bruno’s own use of Cusanus’s ideas. By looking at these differences it is possible to discover the exact historical-philosophical position of Bovelles: unlike Giordano Bruno, Bovelles did not aim at a humanistic revision of Cusanus. His thought presents a unique and brilliant philosophical crossroad of different traditions, in which we can recognize the Renaissance as a conservative memory of the heritage of medieval philosophy.