I offer a novel reading in this dissertation of René Descartes’s (1596–1650) skepticism in his work Meditations on First Philosophy (1641–1642). I specifically aim to answer the following problem: How is Descartes’s skepticism to be read in accordance with the rest of his philosophy? This problem can be divided into two more general questions in Descartes scholarship: How is skepticism utilized in the Meditations, and what are its intentions and relation to the preceding philosophical tradition? -/- I approach the topic (...) from both a historical and a text-based analysis, combining textual and contextual research. I examine Descartes’s skepticism against two main traditions in the historical analysis: philosophical skepticism and Aristotelian Scholasticism. I argue that skepticism in the Meditations is intended to oppose and upheave both Scholasticism and skepticism. The intended results of the work are not merely epistemological but also metaphysical and even ethical. Furthermore, these ambitions cannot be neatly distinguished but merge into each other. -/- The third historical context against which the skeptical meditations are examined is the literary genre of meditative exercises, particularly from the 1500–1600’s, which, while religiously and spiritually oriented, likewise provided the practitioner with an enlightened understanding of self-knowledge and their cognitive place in the world on the way to closer spiritual proximity to God. I argue by this reading that the skepticism of the Meditations is an attentive, meditational cognitive exercise that is not merely instrumental and methodological but is to have a genuine and serious (psychologically real) effect on our thinking. The skeptical meditation is not simply a theoretical thought experiment but is to be seriously practiced as a transformative process of reorienting one’s cognitive framework to discover truth, certainty, and a way to a happy, tranquil, and virtuous life. -/- I offer a close reading in the textual analysis of the first three meditations of the Meditations. I argue that the meditative skepticism employed in the work does not reject the previous beliefs but suspends judgment on them, withdrawing assent until further evidence can be found. I introduce a new term into Descartes scholarship in this analysis, based on the terminology of ancient skepticism: Cartesian epochē (gr. epochē, suspension, withdrawal). Instead of rejecting previous beliefs or assenting to the probably false, the skeptical procedure of the Meditations is argued to emulate in important ways the suspension of judgment on equally balanced reasons in ancient Pyrrhonian skepticism. Novel interpretations are presented along the way of the will’s freedom, of the First Meditation’s skeptical scenarios, of the cogito, and of the vindication of metaphysical certainty, as well as a clarification of the Cartesian Circle problem. -/- Reinterpreting the relation of Descartes’s skepticism to the preceding historical and literary traditions leads to a new look at the skeptical method itself. Presenting a new interpretation of skepticism in the Meditations leads at the same time to a new look at its relation to the historical context. The two research questions are, then, intrinsically tied together. -/- My focus in the study is on the Meditations, but I also reference and discuss Descartes’s other philosophical works, as well as his correspondence, when necessary. (shrink)