This paper examines Leibniz's engagement with Maimonides' Guide of the Perplexed within the long-standing tradition of its reception, while highlighting the originality of Leibniz's position. From its inception, the Guide functioned—according to Leo Strauss's influential interpretation—as a deliberately esoteric and exoteric work, conceived not primarily as a philosophical treatise but as a "guide" for a correct hermeneutics of Scripture. Its central aim was to regulate the reader's approach to biblical language, imagination, and intuition when confronting the most sensitive questions of physics (Work of Creation) and metaphysics (Work of the Chariot). Over time, however, the destiny of the Guide shifted. It came to be studied predominantly as a philosophical text on cosmology and metaphysics, often detached from its original hermeneutical and pedagogical function. This reduction is already visible in medieval Jewish philosophy, notably in Gersonides and Crescas, where the Guide is treated mainly as a source of doctrinal positions rather than as a method for reading and disciplining interpretation. Leibniz enters this tradition with a distinctive agenda: the construction of a monumental modern synthesis of metaphysics and the emerging natural sciences. From this perspective, he appears as an atypical yet exceptional reader of Maimonides. On the one hand, Leibniz demonstrates an acute sensitivity to the dual esoteric/exoteric structure of the Guide, recognizing its strategic use of concealment, analogy, and graded access to truth. On the other hand, he engages seriously with its doctrinal content, particularly concerning the eternity of the world and the rational intelligibility of creation—issues that resonate with his own reflections on contingency and the best of all possible worlds. The paper argues that his reading of Maimonides exemplifies a non-reductive approach capable of preserving the unity of these domains while respecting their internal differentiation.